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Ligand ceramide

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

BRENDA

ceramide biosynthesis, sphingosine metabolism

KEGG

Adipocytokine signaling pathway, AGE-RAGE signaling pathway in diabetic complications, Diabetic cardiomyopathy, Insulin resistance, Leishmaniasis, Necroptosis, Neurotrophin signaling pathway, Sphingolipid metabolism, Sphingolipid signaling pathway more

MetaCyc

ceramide de novo biosynthesis, ceramide degradation (generic), ceramide phosphoethanolamine biosynthesis, gala-series glycosphingolipids biosynthesis, ganglio-series glycosphingolipids biosynthesis, globo-series glycosphingolipids biosynthesis, lacto-series glycosphingolipids biosynthesis, neolacto-series glycosphingolipids biosynthesis, sphingolipid biosynthesis (mammals), sphingomyelin metabolism, sphingosine and sphingosine-1-phosphate metabolism more

Show all BRENDA pathways known for ceramide

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (20 results)

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Show Natural Substrate (20 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.19.18

(4E)-sphing-4-enine ceramide + ferrocytochrome b5 + O2 + H+ = (4E,8E)-sphing-4,8-dienine ceramide + ferricytochrome b5 + H2O

700049, 726865, 658684

-

2.4.1.47

UDP-galactose + ceramide = UDP + D-galactosylceramide

489240

-

2.4.1.80

UDP-glucose + an N-acylsphingosine = UDP + a D-glucosyl-N-acylsphingosine

736201

-

2.4.1.80

UDP-glucose + ceramide = UDP + glucosylceramide

722902, 658310, 659376, 657538

-

2.4.1.80

UDP-glucose + N-acylsphingosine = UDP + D-glucosyl-N-acylsphingosine

489421, 489418, 489422, 489420, 489424, 489417, 489416, 489415, 489405, 489410, 489414, 489404, 489413, 658382, 658636, 682224, 681073, 679436, 682504, 680834

-

2.7.1.138

ATP + ceramide = ADP + ceramide 1-phosphate

661763, 662201, 662431, 662592, 700070, 660886, 662591, 697229, 699089, 696440, 699665, 699827, 737976, 738825, 739165, 760632, 761664, 738014, 738824, 760496, 760851, 761586, 762163, 661860, 661653, 640965, 701002

-

2.7.1.138

ceramide + ATP = ceramide 1-phosphate + ADP

673703, 691938, 691965, 691127, 693223, 690671, 675274, 690404, 693454, 692307, 694006, 690700, 692594, 691364, 690698, 671789, 693522, 690416, 694266

-

2.7.8.27

a ceramide + a phosphatidylcholine = a sphingomyelin + a 1,2-diacyl-sn-glycerol

737844, 739480, 738936, 737776, 738955

-

2.7.8.27

ceramide + phosphatidylcholine = sphingomyelin + 1,2-diacyl-sn-glycerol

708149, 707360, 667142

-

2.7.8.27

phosphatidylcholine + ceramide = sphingomyelin + 1,2-diacyl-sn-glycerol

721280

-

2.7.8.27

phosphatidylcholine + ceramide = sphingomyelin + diacylglycerol

669649

-

2.4.1.80

3 entries

2.7.1.138

2 entries

2.7.8.27

4 entries

2.7.8.3

cytidine diphosphate choline + N-acyl-threo-trans-sphingosine = CMP + sphingomyelin

645383, 645384, 645388, 645389, 645385, 645387, 645390

-

2.7.8.B14

a ceramide + a phosphatidylethanolamine = a ceramide phosphoethanolamine + a 1,2-diacyl-sn-glycerol

738578

-

3.5.1.23

ceramide + H2O = carboxylate + sphingosine

720471

-

3.5.1.23

ceramide + H2O = fatty acid + sphingosine

755557, 754889

-

3.5.1.23

ceramide + H2O = sphingosine + a fatty acid

753222, 753850, 712206

-

3.5.1.23

ceramide + H2O = sphingosine + fatty acid

720416, 715623, 719536, 696396, 711949, 712467, 712489, 718697, 719918, 720438, 720471, 711520, 700748, 700448, 711710, 711799

-

3.5.1.23

N-acyl-sphingosine + H2O = a carboxylate + sphingosine

669517

-

3.5.1.23

N-acylsphingosine + H2O = a carboxylate + sphingosine

664589, 664159

-

3.5.1.23

N-acylsphingosine + H2O = carboxylate + sphingosine

733093, 735256, 733290

-

3.5.1.23

7 entries

In Vivo Product in Enzyme-catalyzed Reactions (25 results)

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Show Natural Product (25 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.19.17

dihydroceramide + ferrocytochrome b5 + O2 + H+ = (4E)-sphing-4-enine ceramide + ferricytochrome b5 + H2O

-

-

1.14.19.17

dihydroceramide + reduced acceptor + O2 + H+ = (4E)-sphing-4-enine ceramide + acceptor + H2O

-

-

1.14.19.17

a dihydroceramide + 2 ferrocytochrome b5 + O2 + 2 H+ = a (4E)-sphing-4-enine ceramide + 2 ferricytochrome b5 + 2 H2O

-

-

1.14.19.17

3 entries

2.3.1.298

fatty acyl-CoA + dihydrosphingosine = ceramide + CoA

-

-

3.1.4.12

a sphingomyelin + H2O = a ceramide + choline phosphate

-

-

3.1.4.12

a sphingomyelin + H2O = a ceramide + phosphocholine

-

-

3.1.4.12

sphingomyelin + H2O = ceramide + phosphocholine

-

-

3.1.4.12

sphingomyelin + H2O = ceramide + phosphorylcholine

-

-

3.1.4.12

sphingomyelin + H2O = ceramide + sphingosine

-

-

3.1.4.12

sphingomyelin + H2O = N-acylsphingosine + choline phosphate

651801, 653103, 650584, 650502, 650366, 652972, 652090, 653120, 651315, 652701, 649984, 649682, 649563, 652601, 652461, 653652, 652373, 652974, 651708, 650323, , 653119, 652543, 652444, 651338, 651148, 652079, 652706

-

3.1.4.12

6 entries

3.1.4.3

sphingomyelin + H2O = ceramide + phosphorylcholine

135299, 135292

-

3.2.1.123

oligoglycosylglucosyl-(1<->1)-ceramide + H2O = ceramide + oligoglycosylglucose

-

-

3.2.1.45

beta-glucosylceramide + H2O = D-glucose + ceramide

-

-

3.2.1.45

D-glucosylceramide + H2O = D-glucose + ceramide

-

-

3.2.1.45

glucocerebroside + H2O = ceramide + D-glucose

-

-

3.2.1.45

glucocerebroside + H2O = D-glucose + ceramide

-

-

3.2.1.45

glucocerebroside + H2O = glucose + ceramide

-

-

3.2.1.45

glucosylceramide + H2O = beta-D-glucose + ceramide

-

-

3.2.1.45

glucosylceramide + H2O = D-glucose + ceramide

-

-

3.2.1.46

D-galactosylceramide + H2O = D-galactose + ceramide

-

-

3.2.1.46

D-galactosyl-N-acylsphingosine + H2O = D-galactose + N-acylsphingosine

-

-

3.2.1.62

galactosylceramide + H2O = beta-D-galactose + ceramide

208758

-

3.2.1.62

glucosylceramide + H2O = beta-D-glucose + ceramide

208758

-

3.2.1.62

oligoglycosylglucosyl-(1->1)-ceramide + H2O = ceramide + oligoglycosylglucose

-

-

3.2.1.62

glucosylsphingosine + H2O = beta-D-glucose + N-acylsphingosine

208758

-

3.2.1.45

7 entries

3.2.1.46

2 entries

3.2.1.62

4 entries

Substrate in Enzyme-catalyzed Reactions (28 results)

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Show Substrate (28 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.19.18

(4E)-sphing-4-enine ceramide + ferrocytochrome b5 + O2 + H+ = (4E,8E)-sphing-4,8-dienine ceramide + ferricytochrome b5 + H2O

700049, 726865, 658684

-

2.4.1.274

UDP-galactose + ceramide = ?

715415

-

2.4.1.47

UDP-galactose + ceramide = UDP + D-galactosylceramide

489240

-

2.4.1.80

UDP-glucose + an N-acylsphingosine = UDP + a D-glucosyl-N-acylsphingosine

736201

-

2.4.1.80

UDP-glucose + ceramide = UDP + D-glucosyl-ceramide

658717

-

2.4.1.80

UDP-glucose + ceramide = UDP + glucosylceramide

657538, 722902, 658310, 691791, 721726, 704776, 722356, 659376

-

2.4.1.80

CDP-glucose + N-acylsphingosine = CDP + D-glucosyl-N-acylsphingosine

489414

-

2.4.1.80

TDP-glucose + N-acylsphingosine = TDP + D-glucosyl-N-acylsphingosine

489414

-

2.4.1.80

UDP-glucose + N-acylsphingosine = UDP + D-glucosyl-N-acylsphingosine

489421, 489418, 658382, 721726, 489422, 489420, 658636, 489424, 489408, 489414, 489404, 489412, 489318, 489406, 489415, 489416, 489417, 489405, 489407, 489409, 489410, 489413, 489419, 489423, 682224, 681073, 679436, 682504, 680834

-

2.4.1.80

6 entries

2.7.1.107

ATP + ceramide = ADP + ceramide 3-phosphate

640352, 640361, 640362, 640359, 640368

-

2.7.1.138

ATP + ceramide = ADP + ceramide 1-phosphate

661763, 662201, 662431, 662592, 700070, 660886, 661653, 662591, 671750, 671756, 671789, 673703, 675274, 697229, 699089, 671880, 696440, 699665, 699827, 737976, 738825, 739165, 760632, 761664, 738014, 738824, 760496, 760851, 761586, 762163, 661860, 640968, 640965, 640966, 701002

-

2.7.1.138

ceramide + ATP = ceramide 1-phosphate + ADP

690700, 673703, 690698, 692307, 693223, 693454, 675274, 690404, 690671, 691938, 691965, 692594, 693522, 694006, 694266, 691364, 671789, 690416, 691127

-

2.7.1.138

GTP + ceramide = GDP + ceramide 1-phosphate

640965

-

2.7.8.27

a ceramide + a phosphatidylcholine = a sphingomyelin + a 1,2-diacyl-sn-glycerol

737844, 739480, 738936, 737776, 738955

-

2.7.8.27

ceramide + phosphatidylcholine = sphingomyelin + 1,2-diacyl-sn-glycerol

708149, 667142, 707360, 709418, 709422

-

2.7.8.27

phosphatidylcholine + ceramide = sphingomyelin + 1,2-diacyl-sn-glycerol

722907, 723537, 721280, 723307

-

2.7.8.27

phosphatidylcholine + ceramide = sphingomyelin + diacylglycerol

669649

-

2.7.8.3

cytidine diphosphate choline + ceramide = CMP + sphingomyelin

645383, 645386

-

2.7.8.3

cytidine diphosphate choline + N-acyl-threo-trans-sphingosine = CMP + sphingomyelin

645383, 645384, 645388, 645389, 645385, 645387, 645390

-

2.7.1.138

3 entries

2.7.8.27

4 entries

2.7.8.3

2 entries

2.7.8.B14

a ceramide + a phosphatidylethanolamine = a ceramide phosphoethanolamine + a 1,2-diacyl-sn-glycerol

738578

-

3.5.1.23

ceramide + H2O = ?

693589, 754849

-

3.5.1.23

ceramide + H2O = carboxylate + sphingosine

720471

-

3.5.1.23

ceramide + H2O = fatty acid + sphingosine

755557, 754889

-

3.5.1.23

ceramide + H2O = sphingosine + a fatty acid

712206, 753222, 753850

-

3.5.1.23

ceramide + H2O = sphingosine + fatty acid

720416, 715623, 719536, 171991, 696396, 711799, 711949, 712467, 712489, 718697, 719918, 720438, 720471, 171987, 711520, 700748, 700448, 711710, 171988

-

3.5.1.23

N-acyl-sphingosine + H2O = a carboxylate + sphingosine

669517

-

3.5.1.23

N-acylsphingosine + H2O = a carboxylate + sphingosine

664589, 664159, 656154, 656010, 655998, 656224, 657260

-

3.5.1.23

N-acylsphingosine + H2O = carboxylate + sphingosine

733093, 735256, 733290

-

3.5.1.23

8 entries

Product in Enzyme-catalyzed Reactions (85 results)

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Show Product (85 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.19.17

dihydroceramide + ferrocytochrome b5 + O2 + H+ = (4E)-sphing-4-enine ceramide + ferricytochrome b5 + H2O

-

-

1.14.19.17

dihydroceramide + reduced acceptor + O2 + H+ = (4E)-sphing-4-enine ceramide + acceptor + H2O

-

-

1.14.19.17

a dihydroceramide + 2 ferrocytochrome b5 + O2 + 2 H+ = a (4E)-sphing-4-enine ceramide + 2 ferricytochrome b5 + 2 H2O

-

-

1.14.19.17

3 entries

2.3.1.24

an acyl-CoA + sphingosine = CoA + an N-acylsphingosine

486668

-

2.3.1.298

fatty acyl-CoA + dihydrosphingosine = ceramide + CoA

-

-

2.7.8.27

sphingomyelin + diacylglycerol = ceramide + phosphatidylcholine

-

-

3.1.3.4

ceramide 1-phosphate + H2O = ceramide + phosphate

-

-

3.1.3.4

ceramide-1-phosphate + H2O = ceramide + phosphate

-

-

3.1.4.12

a sphingomyelin + H2O = a ceramide + choline phosphate

-

-

3.1.4.12

a sphingomyelin + H2O = a ceramide + phosphocholine

-

-

3.1.4.12

sphingomyelin + H2O = ceramide + phosphocholine

-

-

3.1.4.12

sphingomyelin + H2O = ceramide + phosphorylcholine

-

-

3.1.4.12

sphingomyelin + H2O = ceramide + sphingosine

-

-

3.1.4.12

sphingomyelin + H2O = N-acylsphingosine + choline phosphate

, 652079, 135146, 135153, 135168, 135179, 135180, 651148, 651338, 652444, 652543, 653119, 135163, 135170, 135183, 650323, 651315, 652706, 652974, 653103, 653120, 652090, 652972, 135182, 651708, 135166, 650366, 650502, 650584, 651801, 652701, 649984, 649682, 649563, 652601, 652461, 653652, 652373, 135172, 135173

-

3.1.4.3

sphingomyelin + H2O = ceramide + phosphocholine

652656,

-

3.1.4.3

sphingomyelin + H2O = ceramide + phosphorylcholine

135286, 135297, , 133931, 135299, 135308, 135296, 135298, 135292, 135307

-

3.1.4.3

ceramide aminoethylphosphonate = N-acylsphingosine + aminoethylphosphonate

135298

-

3.1.4.3

ceramide phosphorylethanolamine = N-acylsphingosine + phosphorylethanolamine

135298

-

3.1.4.3

sphingomyelin + H2O = N-acylsphingosine + choline phosphate

-

-

3.1.3.4

2 entries

3.1.4.12

6 entries

3.1.4.3

5 entries

3.2.1.104

glucosylceramide + H2O = D-glucose + ceramide

-

-

3.2.1.123

alpha-L-Fuc-(1->2)-beta-D-Gal-(1->3)-beta-D-GalNAc-(1->4)-(alpha-Neu5Ac-(2->3))-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1')-ceramide + H2O = ceramide + alpha-L-Fuc-(1->2)-beta-D-Gal-(1->3)-beta-D-GalNAc-(1->4)-(alpha-Neu5Ac-(2->3))-beta-D-Gal-(1->4)-beta-D-Glc

-

-

3.2.1.123

alpha-Neu5Ac-(2->3)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1')-ceramide + H2O = ceramide + alpha-Neu5Ac-(2->3)-beta-D-Gal-(1->4)-Glc

-

-

3.2.1.123

beta-D-Gal-(1->3)-beta-D-GalNAc-(1->4)-(alpha-Neu5Ac-(2->3))-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1')-ceramide + H2O = ceramide + beta-D-Gal-(1->3)-beta-D-GalNAc-(1->4)-(alpha-Neu5Ac-(2->3))-beta-D-Gal-(1->4)-beta-D-Glc

-

-

3.2.1.123

beta-D-Gal-(1->4)-beta-D-Glc-(1<->1')-ceramide + H2O = ceramide + beta-D-Gal-(1->4)-Glc

-

-

3.2.1.123

beta-D-GalNAc-(1->3)-alpha-Gal-(1->4)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1')-ceramide + H2O = ceramide + beta-D-GalNAc-(1->3)-alpha-Gal-(1->4)-beta-D-Gal-(1->4)-beta-D-Glc

-

-

3.2.1.123

Fucalpha(1->3)GalNAcalpha(1->3)[Fucalpha(1->2)]Galbeta(1->4)Glcbeta(1-1)ceramide + H2O = Fucalpha(1->3)GalNAcalpha(1->3)[Fucalpha(1->2)]Galbeta(1->4)Glc + ceramide

646687

-

3.2.1.123

Galalpha(1-4)Galbeta(1-4)Glcbeta(1-1)ceramide + H2O = Galalpha(1-4)Galbeta(1-4)Glc + ceramide

-

-

3.2.1.123

Galalpha1-6Galalpha1-6Galbeta1-6Galbeta1-1'ceramide + H2O = ceramide + Galalpha1-6Galalpha1-6Gal

-

-

3.2.1.123

Galalpha1-6Galbeta1-6Galbeta1-1'ceramide + H2O = ceramide + Galalpha1-6Galbeta1-6Gal

-

-

3.2.1.123

Galbeta(1,3)GalNacbeta(1,4)Galbeta(1,4)Glcbeta-1,1'-ceramide + H2O = ceramide + Galbeta(1,3)GalNacbeta(1,4)Galbeta(1,4)Glc

-

-

3.2.1.123

Galbeta(1,3)GalNAcbeta(1,4)[NeuAcalpha(2,3)]Galbeta(1,4)Glcbeta-1,1'-ceramide + H2O = ceramide + Galbeta(1,3)GalNAcbeta(1,4)[NeuAcalpha(2,3)]Galbeta(1,4)Glc

-

-

3.2.1.123

Galbeta(1,3)GalNAcbeta(1,4)[NeuAcalpha(2,8)NeuAcalpha(2,3)]Galbeta(1,4)Glcbeta-1,1'-ceramide + H2O = ceramide + Galbeta(1,3)GalNAcbeta(1,4)[NeuAcalpha(2,8)NeuAcalpha(2,3)]Galbeta(1,4)Glc

-

-

3.2.1.123

Galbeta(1,4)Glcbeta-1,1'-ceramide + H2O = ceramide + Galbeta(1,4)Glc

-

-

3.2.1.123

Galbeta(1,6)Galbeta(1,6)Glcbeta-1,1'-ceramide + H2O = ceramide + Galbeta(1,6)Galbeta(1,6)Glc

-

-

3.2.1.123

Galbeta(1-3)GalNAcbeta(1-4)(NeuAcalpha(2-3))Galbeta(1-4)Glcbeta(1-1)ceramide + H2O = Galbeta(1-3)GalNAcbeta(1-4)(NeuAcalpha(2-3))Galbeta(1-4)Glc + ceramide

, 646687, 646699

-

3.2.1.123

Galbeta(1-3)GalNAcbeta(1-4)(NeuAcalpha(2-8)NeuAcalpha(2-3))Galbeta(1-4)Glcbeta(1-1)ceramide + H2O = Galbeta(1-3)GalNAcbeta(1-4)(NeuAcalpha(2-8)NeuAcalpha(2-3))Galbeta(1-4)Glc + ceramide

-

-

3.2.1.123

Galbeta(1-3)GalNAcbeta(1-4)Galbeta(1-4)Glcbeta(1-1)ceramide + H2O = Galbeta(1-3)GalNAcbeta(1-4)Galbeta(1-4)Glc + ceramide

, 646687

-

3.2.1.123

Galbeta(1-4)Glcbeta(1-1)ceramide + H2O = Galbeta(1-4)Glc + ceramide

, 646687, 646694

-

3.2.1.123

Galbeta(1-6)Galbeta(1-6)Galbeta(1-1)ceramide + H2O = Galbeta(1-6)Galbeta(1-6)Gal + ceramide

646687

-

3.2.1.123

Galbeta1-6Galbeta1-1'ceramide + H2O = ceramide + Galbeta1-6Galbeta

-

-

3.2.1.123

Galbeta1-6Galbeta1-6Galbeta1-1'-ceramide + H2O = ceramide + Galbeta1-6Galbeta1-6Gal

-

-

3.2.1.123

GalNAcalpha(1,4)GalNAcbeta(1,4)GlcNAcbeta(1,3)Manbeta(1,4)Glcbeta-1,1'-ceramide + H2O = ceramide + GalNAcalpha(1,4)GalNAcbeta(1,4)GlcNAcbeta(1,3)Manbeta(1,4)Glc

-

-

3.2.1.123

GalNAcalpha(1-3)GalNAcbeta(1-3)Galalpha(1-4)Galbeta(1-4)Glcbeta(1-1)ceramide + H2O = GalNAcalpha(1-3)GalNAcbeta(1-3)Galalpha(1-4)Galbeta(1-4)Glc + ceramide

-

-

3.2.1.123

GalNAcbeta(1,3)Galalpha(1,4)Galbeta(1,4)Glcbeta-1,1'-ceramide + H2O = ceramide + GalNAcbeta(1,3)Galalpha(1,4)Galbeta(1,4)Glc

-

-

3.2.1.123

GalNAcbeta(1-3)Galalpha(1-4)Galbeta(1-4)Glcbeta(1-1)ceramide + H2O = GalNAcbeta(1-3)Galalpha(1-4)Galbeta(1-4)Glc + ceramide

, 646699

-

3.2.1.123

GalNAcbeta(1-4)(NeuAcalpha(2-3))Galbeta(1-4)Glcbeta(1-1)ceramide + H2O = GalNAcbeta(1-4)(NeuAcalpha(2-3))Galbeta(1-4)Glc + ceramide

, 646687

-

3.2.1.123

GalNAcbeta(1-4)Galbeta(1-4)Glcbeta(1-1)ceramide + H2O = GalNAcbeta(1-4)Galbeta(1-4)Glc + ceramide

-

-

3.2.1.123

GlcA4Me-beta(1,4)[GalNAc-Me-alpha(1,3)]Fucalpha(1,4)GlcNAcbeta(1,2)Manalpha(1,3)[Xylbeta(1,2)]Manbeta(1,4)Glcbeta-1,1'-ceramide + H2O = ceramide + GlcA4Me-beta(1,4)[GalNAc-Me-alpha(1,3)]Fucalpha(1,4)GlcNAcbeta(1,2)Manalpha(1,3)[Xylbeta(1,2)]Manbeta(1,4)Glc

-

-

3.2.1.123

GlcNAcalpha1-2Fucalpha1-3Manbeta1-4Glcbeta1-1'-ceramide + H2O = ceramide + GlcNAcalpha1-2Fucalpha1-3Manbeta1-4Glc

-

-

3.2.1.123

GlcNAcbeta(1-2)Manalpha(1-3)Manbeta(1-4)Glcbeta(1-1)ceramide + H2O = GlcNAcbeta(1-2)Manalpha(1-3)Manbeta(1-4)Glc + ceramide

646687

-

3.2.1.123

Manalpha(1-3)Manbeta(1-4)Glcbeta(1-1)ceramide + H2O = Manalpha(1-3)Manbeta(1-4)Glc + ceramide

646687

-

3.2.1.123

Manbeta(1-4)Glcbeta(1-1)ceramide + H2O = Manbeta(1-4)Glc + ceramide

646687

-

3.2.1.123

monogalactosylceramide + H2O = ceramide + D-galactose

-

-

3.2.1.123

NeuAcalpha(2,3)Galbeta(1,3)GalNAcbeta(1,4)[NeuAcalpha(2,3)]Galbeta(1,4)Glcbeta-1,1'-ceramide + H2O = ceramide + NeuAcalpha(2,3)Galbeta(1,3)GalNAcbeta(1,4)[NeuAcalpha(2,3)]Galbeta(1,4)Glc

-

-

3.2.1.123

NeuAcalpha(2,3)Galbeta(1,3)GalNAcbeta(1,4)[NeuAcalpha(2,8)NeuAcalpha(2,3)]Galbeta(1,4)Glcbeta-1,1'-ceramide + H2O = ceramide + NeuAcalpha(2,3)Galbeta(1,3)GalNAcbeta(1,4)[NeuAcalpha(2,8)NeuAcalpha-2,3]Gal-beta(1,4)Glc

-

-

3.2.1.123

NeuAcalpha(2,3)Galbeta(1,4)Glcbeta-1,1'-ceramide + H2O = ceramide + NeuAcalpha(2,3)Galbeta(1,4)Glc

-

-

3.2.1.123

NeuAcalpha(2-3)Galbeta(1-3)GalNAcbeta(1-4)(NeuAcalpha(2-3))Galbeta(1-4)Glcbeta(1-1)ceramide + H2O = NeuAcalpha(2-3)Galbeta(1-3)GalNAcbeta(1-4)(NeuAcalpha(2-3))Galbeta(1-4)Glc + ceramide

, 646687

-

3.2.1.123

NeuAcalpha(2-3)Galbeta(1-3)GalNAcbeta(1-4)(NeuAcalpha(2-8)NeuAcalpha(2-3))Galbeta(1-4)Glcbeta(1-1)ceramide + H2O = NeuAcalpha(2-3)Galbeta(1-3)GalNAcbeta(1-4)(NeuAcalpha(2-8)NeuAcalpha(2-3))Galbeta(1-4)Glc + ceramide

646691,

-

3.2.1.123

NeuAcalpha(2-3)Galbeta(1-4)Glcbeta(1-1)ceramide + H2O = NeuAcalpha(2-3)Galbeta(1-4)Glc + ceramide

646687,

-

3.2.1.123

NeuAcalpha(2-3)Galbeta(1-4)GlcNAcbeta(1-3)Galbeta(1-4)Glcbeta(1-1)ceramide + H2O = NeuAcalpha(2-3)Galbeta(1-4)GlcNAcbeta(1-3)Galbeta(1-4)Glc + ceramide

, 646687

-

3.2.1.123

NeuAcalpha(2-8)NeuAcalpha(2-3)Galbeta(1-3)GalNAcbeta(1-4)(NeuAcalpha(2-3))Galbeta(1-4)Glcbeta(1-1)ceramide + H2O = NeuAcalpha(2-8)NeuAcalpha(2-3)Galbeta(1-3)GalNAcbeta(1-4)(NeuAcalpha(2-3))Galbeta(1-4)Glc + ceramide

646687

-

3.2.1.123

NeuAcalpha(2-8)NeuAcalpha(2-3)Galbeta(1-3)GalNAcbeta(1-4)(NeuAcalpha(2-8)NeuAcalpha(2-3))Galbeta(1-4)Glcbeta(1-1)ceramide + H2O = NeuAcalpha(2-8)NeuAcalpha(2-3)Galbeta(1-3)GalNAcbeta(1-4)(NeuAcalpha(2-8)NeuAcalpha(2-3))Galbeta(1-4)Glc + ceramide

646691,

-

3.2.1.123

NeuAcalpha(2-8)NeuAcalpha(2-3)Galbeta(1-4)Glcbeta(1-1)ceramide + H2O = NeuAcalpha(2-8)NeuAcalpha(2-3)Galbeta(1-4)Glc + ceramide

-

-

3.2.1.123

oligoglycosylglucosyl-(1<->1)-ceramide + H2O = ceramide + oligoglycosylglucose

-

-

3.2.1.45

beta-glucosylceramide + H2O = D-glucose + ceramide

-

-

3.2.1.45

D-glucocerebroside + H2O = D-glucose + ceramide

-

-

3.2.1.45

D-glucosylceramide + H2O = D-glucose + ceramide

-

-

3.2.1.45

glucocerebroside + H2O = beta-D-glucose + ceramide

-

-

3.2.1.45

glucocerebroside + H2O = ceramide + D-glucose

-

-

3.2.1.45

glucocerebroside + H2O = D-glucose + ceramide

-

-

3.2.1.45

glucocerebroside + H2O = glucose + ceramide

-

-

3.2.1.45

glucosylceramide + H2O = beta-D-glucose + ceramide

-

-

3.2.1.45

glucosylceramide + H2O = D-glucose + ceramide

-

-

3.2.1.46

D-galactosylceramide + H2O = D-galactose + ceramide

-

-

3.2.1.46

D-galactosyl-N-acylsphingosine + H2O = D-galactose + N-acylsphingosine

-

-

3.2.1.62

galactosylceramide + H2O = beta-D-galactose + ceramide

208758,

-

3.2.1.62

galactosylceramide + H2O = ceramide + D-galactose

-

-

3.2.1.62

glucosylceramide + H2O = beta-D-glucose + ceramide

208758,

-

3.2.1.62

glucosylceramide + H2O = ceramide + D-glucose

-

-

3.2.1.62

oligoglycosylglucosyl-(1->1)-ceramide + H2O = ceramide + oligoglycosylglucose

-

-

3.2.1.62

glucosylsphingosine + H2O = beta-D-glucose + N-acylsphingosine

208758

-

3.2.1.62

glycosyl-N-acylsphingosine + H2O = N-acylsphingosine + a sugar

-

-

3.5.1.23

4-nitrobenzo-2-oxa-1,3-diazole-C12-ceramide + H2O = 4-nitrobenzo-2-oxa-1,3-diazole-dodecanoic acid + ceramide

-

-

3.5.1.23

D-erythro-4-nitrobenzo-2-oxa-1,3-diazole-C12-ceramide + H2O = D-erythro-4-nitrobenzo-2-oxa-1,3-diazole-dodecanoic acid + ceramide

-

-

3.5.1.23

sphingosine + fatty acid = ceramide

171987

-

3.2.1.123

44 entries

3.2.1.45

9 entries

3.2.1.46

2 entries

3.2.1.62

7 entries

3.5.1.23

3 entries

Activator in Enzyme-catalyzed Reactions (5 results)

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Show Activating Compound (5 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

2.3.1.43

30% activation, stimulation of synthesis of 20:4 cholesteryl ester and 18:2 cholesteryl ester, but not of 16:0 cholesteryl ester, a phosphocholine ether matrix abolishes the activation effect

672155

-

3.1.3.16

ceramide induces increase of PP2A activity

693780

-

3.1.4.12

-

135149

-

3.1.6.8

inhibition or activation depends on substrate

135676

-

3.4.22.60

-

670408

-

Inhibitor in Enzyme-catalyzed Reactions (17 results)

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Show Inhibitors (17 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.34

treatment with exogenous ceramides, or increasing the endogenous ceramide levels inhibits HMGCR by 60–80%

695855

-

2.4.1.212

-

737217

-

2.7.1.107

-

640359

-

2.7.1.154

selective inhibition of PI3KC2beta

761670

-

2.7.1.174

-

687738

-

2.7.7.15

-

660981

-

2.7.7.15

short chain ceramides

662451

-

2.7.7.15

2 entries

2.7.8.27

-

667142

-

3.1.4.12

-

135172

-

3.1.4.12

23% inhibition

135173

-

3.1.4.12

feedback inhibition

679082

-

3.1.4.12

product feedback inhibition; product feedback inhibition

677878

-

3.1.4.12

strong inhibition in the presence of 0.4 mM linoleic acid

653103

-

3.1.4.12

5 entries

3.1.4.4

inhibits PLD at the catalytic subunit by competing with phosphatidylinositol-4,5-bisphosphate. Ceramide levels are increased coincidentally with reduced PLD activity in senescent cells. Treatment of cells with ceramide results in a dose-dependent decrease in PLD activity and diacylglycerol accumulation

709924

-

3.1.6.8

inhibition or activation depends on substrate

135676

-

3.2.1.23

hydrolysis of lactosyl ceramide

171319

-

7.2.2.3

mediates enzyme inhibition to about 60% by activating protein kinase A and protein kinase Czeta, that regulate ion transporter activities. Inhibition of the kinase reverses the inhibitory effect of ceramide on Na+-ATPase

711013

-

Enzyme Kinetic Parameters

K_M Value (12 results)

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Show KM Value (12 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.4.1.80

0.054

-

-

489410

2.4.1.80

0.08

-

-

489404

2.4.1.80

0.292

-

-

489407

2.4.1.80

3 entries

2.7.1.107

0.23

-

pH 6.6, 25°C

640362

2.7.1.138

0.045

-

pH 7.0, 22°C

640966

2.7.1.138

0.187

-

recombinant enzyme

661860

2.7.1.138

0.19

-

pH 7.2, 30°C, recombinant ceramide kinase

640968

2.7.1.138

0.194

-

assay mixture is composed of 0.88 mM ceramide, 1 mM cardiolipin, 1.5% beta-octylglucoside, 0.2 mM diethylenetriaminepenta-acetic acid, 20 mM MOPS, pH 7.2, 50 mM NaCl, 10 mM dithiothreitol, 2 mM EGTA, 3 mM CaCl2 and 0.5 mM ATP, at 30°C

671880

2.7.1.138

0.205

-

assay mixture is composed of 0.88 mM ceramide, 1 mM cardiolipin, 1.5% beta-octylglucoside, 0.2 mM diethylenetriaminepenta-acetic acid, 20 mM MOPS, pH 7.2, 50 mM NaCl, 10 mM dithiothreitol, 2 mM EGTA, 3 mM CaCl2 and 0.5 mM ATP, at 30°C

671880

2.7.1.138

19.2

-

recombinant mutant L10I

661763

2.7.1.138

20.9

-

recombinant wild-type enzyme

661763

2.7.1.138

7 entries

3.5.1.23

0.3

-

-

171987

IC₅₀ Value (1 result)

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Show IC50 Value (1 entry)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

7.2.2.3

0.0001

-

pH 7.4, 37°C

711013

References & Links

Literature References (231)

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Show Reference (231 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

133931

-

Phospholipases

1971

Hanahan, D.J.

The Enzymes, 3rd Ed. (Boyer, P. D. , ed. )

5

71-85

135146

2538416

A new Zn2+-stimulated sphingomyelinase in fetal bovine serum

1989

Spence, M.W.; Byers, D.M.; Palmer, F.B.St.C.; Cook, H.W.

J. Biol. Chem.

264

5358-5363

135149

2825797

Acid sphingomyelinase from human urine: purification and characterization

1987

Quintern, L.E.; Weitz, G.; Nehrkorn, H.; Tager, J.M.; Schram, A.W.; Sandhoff, K.

Biochim. Biophys. Acta

922

323-336

135153

-

Immunological properties of urinary sphingomyelinase

1984

Schram, A.W.; Weitz, G.; Driessen, M.; Brouwer-Kelder, E.M.; Sandhoff, K.; Barranger, J.A.; Tager, J.M.

Biochem. Soc. Trans.

12

1027-1028

135163

37279

The subcellular localization of neutral sphingomyelinase in rat liver

1979

Hostetler, K.Y.; Yazaki, P.J.

J. Lipid Res.

20

456-463

135166

23854

Studies on sphingomyelinase of Bacillus cereus. I. Purification and properties

1978

Ikezawa, H.; Mori, M.; Ohyabu, T.; Taguchi, R.

Biochim. Biophys. Acta

528

247-256

135168

19083

The isolation and characterization of sphingomyelinase from human placental tissue

1977

Pentchev, P.G.; Brady, R.O.; Gal, A.E.; Hibbert, S.R.

Biochim. Biophys. Acta

488

312-321

135170

174564

Magnesium-dependent sphingomyelinase

1976

Gatt, S.

Biochem. Biophys. Res. Commun.

68

235-241

135172

5916388

Enzymatic hydrolysis of sphingolipids. II. Hydrolysis of sphingomyelin by an enzyme from rat brain

1966

Barnholz, Y.; Roitman, A.; Gatt, S.

J. Biol. Chem.

241

3731-3737

135173

5911524

Enzymic hydrolysis of sphingomyelin by rat liver

1966

Heller, M.; Shapiro, B.

Biochem. J.

98

763-769

135179

9328299

Purification of a newly identified alkaline sphingomyelinase in human bile and effects of bile salts and phosphatidylcholine on enzyme activity

1997

Duan, R.D.; Nilsson, A.

Hepatology

26

823-830

135180

9240970

Serine protease inhibitors block neutral sphingomyelinase activation, ceramide generation, and apoptosis triggered by daunorubicin

1997

Mansat, V.; Bettaieb, A.; Levade, T.; Laurent, G.; Jaffrezou, J.P.

FASEB J.

11

695-702

135182

9879667

Identification, partial purification, and localization of a neutral sphingomyelinase in rabbit skeletal muscle: neutral sphingomyelinase in skeletal muscle

1998

Gosh, N.; Sabbadini, R.; Chatterjee, S.

Mol. Cell. Biochem.

189

161-168

135183

9852115

Purification and characterization of a membrane bound neutral pH optimum magnesium-dependent and phosphatidylserine-stimulated sphingomyelinase from rat brain

1998

Liu, B.; Hassler, D.F.; Smith, G.K.; Weaver, K.; Hannun, Y.A.

J. Biol. Chem.

273

34472-34479

135286

8722307

Characterization of a phospholipase C produced by Pseudomaonas fluorescens

1996

Ivanov, A.; Titibali, R.W.; Kostadinova, S.

New Microbiol.

19

113-121

135292

1904842

Purification and characterization of an extracellular 29-kilodalton phospholipase C from Listeria monocytogenes

1991

Geoffroy, C.; Raveveau, J.; Beretti, J.L.; Lecroisey, A.; Vazquez-Boland, J.A.; Alouf, J.E.; Berche, P.

Infect. Immun.

59

2382-2388

135296

6329100

Phospholipase C from Clostridium perfringens: Preparation and characterization of homogenous enzyme

1984

Krug, E.; Kent, C.

Arch. Biochem. Biophys.

231

400-410

135297

6811552

Phospholipase C (heat-labile hemolysin) of Pseudomonas aeruginosa: Purification and preliminary characterization

1982

Berka, R.M.; Vasil, M.L.

J. Bacteriol.

152

239-245

135298

6268935

Phospholipase C from Clostridium perfringens

1981

Takahashi, T.; Sugahara, T.; Ohsaka, A.

Methods Enzymol.

71

710-725

135299

-

Phospholipase C from Bacillus cereus

1981

Little, C.

Methods Enzymol.

71

725-730

135307

5411

Studies on phospholipases from Streptomyces. Purification and properties of Streptomyces hachijoensis phospholipase C

1975

Okawa, Y.; Yamaguchi, T.

J. Biochem.

78

537-545

135308

4216738

Phospholipase C (phosphatidylcholine cholinephosphohydrolase, EC 3.1.4.3) from Bacillus cereus

1974

Zwaal, R.F.A.; Roelofsen, B.

Methods Enzymol.

32

154-161

135676

235289

Comparison of the cerebroside sulphatase and the arylsulphatase activity of human sulphatase A in the absence of activators

1975

Stinshoff, K.; Jatzkewitz, H.

Biochim. Biophys. Acta

377

126-138

171319

-

beta-Galactosidase from rat brain

1969

Gatt, S.

Methods Enzymol.

14

156-161

171987

5916387

Enzymatic hydrolysis of sphingolipids. I. Hydrolysis and synthesis of ceramides by an enzyme from rat brain

1966

Gatt, S.

J. Biol. Chem.

241

3724-3730

171988

10488143

Purification and characterization of a membrane-bound nonlysosomal ceramidase from rat brain

1999

Bawab, S.E; Bielawska, A.; Hannun, Y.A.

J. Biol. Chem.

274

27948-27955

171991

8581356

Sulfatide and sphingomyelin loading of living cells as tools for the study of ceramide turnover by lysosomal ceramidase - implications for the diagnosis of Farber disease

1995

Levade, T.; Tempesta, M.C.; Moser, H.W.; Fensom, A.H.; Harzer, K.; Moser, A.B.; Salvayre, R.

Biochem. Mol. Med.

54

117-125

208758

6790523

The glycosylceramidase in the murine intestine. Purification and substrate specificity

1981

Kobayashi, T.; Suzuki, K.

J. Biol. Chem.

256

7768-7773

486668

9655376

Partial purification and characterization of sphingosine N-acyltransferase (ceramide synthase) from bovine liver mitochondrion-rich fraction

1998

Shimeno, H.; Soeda, S.; Sakamoto, M.; Kouchi, T.; Kowakame, T.; Kihara, T.

Lipids

33

601-605

489240

5807218

Enzymic synthesis of cerebroside from ceramide and uridine diphosphate galactose

1969

Fujino, Y.; Nakano, M.

Biochem. J.

113

573-575

489318

8509426

Synthesis and characterization of a new class of inhibitors of membrane-associated UDP-glycosyltransferases

1993

Paul, P.; Lutz, T.M.; Osborn, C.; Kyosseva, S.; Elbein, A.D.; Towbin, H.; Radominska, A.; Drake, R.R.

J. Biol. Chem.

268

12933-12938

489404

4631392

Enzymatic synthesis of glucocerebroside by a glucosyltransferase from embryonic chicken brain

1973

Basu, S.; Kaufman, B.; Roseman, S.

J. Biol. Chem.

248

1388-1394

489405

4784456

UDP-glucose: ceramide glucosyltransferase of rat brain: an association with smooth microsomes and requirement of an intact membrane for enzyme activity

1973

Shah, S.N.

Arch. Biochem. Biophys.

159

143-150

489406

2148864

Glucosyceramide synthase of mouse kidney: further characterization with an improved assay method

1990

Shukla, G.S.; Radin, N.S.

Arch. Biochem. Biophys.

283

372-378

489407

1533793

A rapid and simple assay method for UDP-glucose:ceramide glucosyltransferase

1992

Matsuo, N.; Nomura, T.; Imokawa, G.

Biochim. Biophys. Acta

1116

97-103

489408

454641

Short chain ceramides as substrates for glucocerebroside synthetase. Differences between liver and brain enzymes

1979

Vunnam, R.R.; Radin, N.S.

Biochim. Biophys. Acta

573

73-82

489409

2141281

Solubilization of UDPglucose-ceramide glucosyltransferase from the Golgi apparatus

1990

Durieux, I.; Martel, M.B.; Got, R.

Biochim. Biophys. Acta

1024

263-266

489410

3156635

UDPglucose-ceramide glucosyltransferase from porcine submaxillary glands is associated with the Golgi apparatus

1985

Coste, H.; Martel, M.B.; Azzar, G.; Got, R.

Biochim. Biophys. Acta

814

1-7

489412

8534980

Enzymatic formation of plant cerebroside: properties of UDP-glucose:ceramide glucosyltransferase in radish seedlings

1995

Nakayama, M.; Kojima, M.; Ohnishi, M.; Ito, S.

Biosci. Biotechnol. Biochem.

59

1882-1886

489413

8643456

Expression cloning of a cDNA for human ceramide glucosyltransferase that catalyzes the first glycosylation step of glycosphingolipid synthesis

1996

Ichikawa, S.; Sakiyama, H.; Suzuki, G.; Hidari, K.I.P.J.; Hirabayashi, Y.

Proc. Natl. Acad. Sci. USA

93

4638-4643

489414

8567691

Purification and characterization of UDP-glucose:ceramide glucosyltransferase from rat liver Golgi membranes

1996

Paul, P.; Kamisaka, Y.; Marks, D.L.; Pagano, R.E.

J. Biol. Chem.

271

2287-2293

489415

9507988

Glucosylceramide synthase activity in murine epidermis: quantitation, localization, regulation, and requirement for barrier homeostasis

1998

Chujor, C.S.; Feingold, K.R.; Elias, P.M.; Holleran, W.M.

J. Lipid Res.

39

277-285

489416

9695839

Glucosylceramide synthase and glycosphingolipid synthesis

1998

Ichikawa, S.; Hirabayashi, Y.

Trends Cell Biol.

8

198-202

489417

12538495

Possible role of ceramide as an indicator of chemoresistance: decrease of the ceramide content via activation of glucosylceramide synthase and sphingomyelin synthase in chemoresistant leukemia

2003

Itoh, M.; Kitano, T.; Watanabe, M.; Kondo, T.; Yabu, T.; Taguchi, Y.; Iwai, K.; Tashima, M.; Uchiyama, T.; Okazaki, T.

Clin. Cancer Res.

9

415-423

489418

9867864

Oligomerization and topology of the Golgi membrane protein glucosylceramide synthase

1999

Marks, D.L.; Wu, K.; Paul, P.; Kamisaka, Y.; Watanabe, R.; Pagano, R.E.

J. Biol. Chem.

274

451-456

489419

-

Histidine-193 of rat glucosylceramide synthase resides in a UDP-glucose-and inhibitor (D-threo-1-phenyl-2-decanoylamino-3-morpholinopropan-1-ol)-binding region: a biochemical and mutational study

1999

Wu, K.; Marks, D.L.; Watanabe, R.; Paul, P.; Rajan, N.; Pagano, R.E.

Biochem. J.

341

395-400

489420

10563309

Glucosylceramide synthase: assay and properties

2000

Shayman, J.A.; Abe, A.

Methods Enzymol.

311

42-49

489421

10563310

Methods for studying glucosylceramide synthase

2000

Marks, D.L.; Paul, P.; Kamisaka, Y.; Pagano, R.E.

Methods Enzymol.

311

50-59

489422

11171194

Characterization of UDP-glucose: ceramide glucosyltransferases from different organisms

2000

Leipelt, M.; Warnecke, D.C.; Hube, B.; Zahringer, U.; Heinz, E.

Biochem. Soc. Trans.

28

751-752

489423

11337504

Identification of active site residues in glucosylceramide synthase. A nucleotide-binding/catalytic motif conserved with processive beta-glycosyltransferases

2001

Marks, D.L.; Dominguez, M.; Wu, K.; Pagano, R.E.

J. Biol. Chem.

276

26492-26498

489424

12139966

Molecular cloning of Chinese hamster ceramide glucosyltransferase and its enhanced expression in peroxisome-defective mutant Z65 cells

2002

Saito, M.; Fukushima, Y.; Tatsumi, K.; Bei, L.; Fujiki, Y.; Iwamori, M.; Igarashi, T.; Sakakihara, Y.

Arch. Biochem. Biophys.

403

171-178

640352

1323028

Diacylglycerol kinase from Escherichia coli

1992

Walsh, J.P.; Bell, R.M.

Methods Enzymol.

209

153-162

640359

1309777

Ceramide is a competitive inhibitor of diacylglycerol kinase in vitro and in intact human leukemia (HL-60) cells

1992

Younes, A.; Kahn, D.W.; Besterman, J.M.; Bittman, R.; Byun, H.S.; Kolesnick, R.N.

J. Biol. Chem.

267

842-847

640361

6303781

Lipid dependence of diacylglycerol kinase from Escherichia coli

1983

Bohnenberger, E.; Sandermann, H.

Eur. J. Biochem.

132

645-650

640362

218816

Diglyceride kinase from Escherichia coli. Purification in organic solvent and some properties of the enzyme

1979

Bohnenberger, E.; Sandermann, H.

Eur. J. Biochem.

94

401-407

640368

205418

Properties of microsomal and soluble diacylglycerol kinase in rat liver

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