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Ligand phytosphingosine

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (6 results)

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Show Natural Substrate (6 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.19.29

C18-phytosphinganine + ferrocytochrome b5 + O2 + H+ = C18-8-phytosphingenine + ferricytochrome b5 + H2O

657640

-

1.14.19.29

C18-phytosphinganine + ferrocytochrome b5 + O2 + H+ = DELTA8-trans/cis-C18-phytosphingenine + ferricytochrome b5 + H2O

657892

-

2.3.1.297

hexacosanoyl-CoA + phytosphingosine = CoA + N-hexacosanoylphytosphingosine

752718

-

2.3.1.297

lignoceroyl-CoA + phytosphingosine = N-lignoceroylphytosphinganine + CoA

752718

-

1.14.19.29

2 entries

2.3.1.297

2 entries

2.3.1.298

an ultra-long-chain fatty acyl-CoA + phytosphingosine = phytoceramide + CoA

753522

-

2.7.1.91

ATP + phytosphingosine = ADP + phytosphingosine 1-phosphate

661509, 663137

-

In Vivo Product in Enzyme-catalyzed Reactions (1 result)

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Show Natural Product (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.5.1.23

phytoceramide + H2O = phytosphingosine + fatty acid

0

-

Substrate in Enzyme-catalyzed Reactions (12 results)

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Show Substrate (12 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.19.18

4-hydroxysphinganine + ferrocytochrome b5 + O2 + H+ = 4-hydroxy-trans-8-sphingenine + ferricytochrome b5 + H2O

658490

-

1.14.19.18

C18-phytosphingosine + ferrocytochrome b5 + O2 + H+ = (8Z)-C18-phytosphingenine + (8E)-C18-phytosphingenine + ferricytochrome b5 + H2O

728540

-

1.14.19.29

C18-phytosphinganine + ferrocytochrome b5 + O2 + H+ = C18-8-phytosphingenine + ferricytochrome b5 + H2O

657640

-

1.14.19.29

C18-phytosphinganine + ferrocytochrome b5 + O2 + H+ = DELTA8-trans/cis-C18-phytosphingenine + ferricytochrome b5 + H2O

657892

-

1.14.19.18

2 entries

1.14.19.29

2 entries

1.14.19.4

4-hydroxysphinganine + reduced acceptor + H2O = 4-hydroxy-trans-8-sphingenine + acceptor + H2O

658490

-

2.3.1.24

a fatty acyl-CoA + phytosphingosine = CoA + an N-acylphytosphingosine

757289

-

2.3.1.24

acyl-CoA + phytosphingosine = CoA + N-acylphytosphingosine

756124

-

2.3.1.24

stearoyl-CoA + phytosphingosine = CoA + N-stearoylphytosphingosine

756397

-

2.3.1.297

hexacosanoyl-CoA + phytosphingosine = CoA + N-hexacosanoylphytosphingosine

752718

-

2.3.1.297

lignoceroyl-CoA + phytosphingosine = N-lignoceroylphytosphinganine + CoA

752718

-

2.3.1.24

3 entries

2.3.1.297

2 entries

2.3.1.298

an ultra-long-chain fatty acyl-CoA + phytosphingosine = phytoceramide + CoA

753522

-

2.7.1.91

ATP + phytosphingosine = ADP + phytosphingosine 1-phosphate

661509, 674380, 661329, 663137, 661860

-

Product in Enzyme-catalyzed Reactions (11 results)

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Show Product (11 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.18.5

D-erythro-sphinganine + NADH + H+ + O2 = 4-hydroxysphinganine + NAD+ + H2O

0

-

1.14.18.5

D-erythro-sphinganine + NADPH + H+ + O2 = 4-hydroxysphinganine + NADP+ + H2O

0

-

1.14.18.5

dihydrosphingosine + NADPH + H+ + O2 = phytosphingosine + NADP+ + H2O

0

-

1.14.18.5

DL-erythro-dihydrosphingosine + reduced acceptor + H+ + O2 = phytosphingosine + acceptor + H2O

0

-

1.14.18.5

sphingosine + reduced acceptor + H+ + O2 = phytosphingosine + acceptor + H2O

0

-

3.5.1.23

N-dodecanoyl-7-nitrobenz-2-oxa-1,3,4-diazole-D-erythro-phytosphingosine + H2O = 12-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]dodecanate + D-erythro-phytosphingosine

0

-

3.5.1.23

11-eicosenoyl-phytoceramide + H2O = phytosphingosine + 11-eicosenoic acid

0

-

3.5.1.23

N-arachidonoyl-phytoceramide + H2O = phytosphingosine + arachidonate

0

-

3.5.1.23

N-oleoyl-phytoceramide + H2O = phytosphingosine + oleate

0

-

3.5.1.23

N-[12-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]lauroyl]-phytosphingosine + H2O = N-12-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]laurate + phytosphingosine

0

-

3.5.1.23

phytoceramide + H2O = phytosphingosine + fatty acid

0

-

1.14.18.5

5 entries

3.5.1.23

6 entries

Inhibitor in Enzyme-catalyzed Reactions (9 results)

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Show Inhibitors (9 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

2.3.1.22

-

486608

-

2.4.1.34

non-competitive inhibition

489077

-

2.7.1.174

-

687738

-

2.7.1.91

0.0025 mM, 21% inhibition; 0.0025 mM, 64% inhibition

687479

-

3.1.3.4

-

653123, 751277

-

3.1.3.4

inhibition of PAH1

693238

-

3.1.3.4

2 entries

3.1.4.12

-

135181

-

3.5.1.23

-

171990

-

3.5.1.23

recombinant CDase, 0.02 mM, 60% inhibition

657260

-

3.5.1.23

2 entries

Enzyme Kinetic Parameters

K_M Value (2 results)

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Show KM Value (2 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.3.1.297

0.0069

-

pH 7.5, 30°C, LOH1

752718

2.3.1.297

0.023

-

pH 7.5, 30°C, LOH3

752718

2.3.1.297

2 entries

References & Links

Literature References (24)

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Show Reference (24 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

135181

9126282

Characterization of a sphingomyelinase activity in Saccharomyces cerevisiae

1997

Ella, K.M.; Qi, C.; Dolan, J.W.; Thompson, R.P.; Meier, K.E.

Arch. Biochem. Biophys.

340

101-110

171990

9603946

Purification and characterization of a novel ceramidase from Pseudomonas aeruginoa

1998

Okino, N.; Tani, M.; Imayama, S.; Ito, M.

J. Biol. Chem.

273

14368-14373

486608

7669782

Sphingosine inhibits rat hepatic monoacylglycerol acyltransferase in Triton X-100 mixed micelles and isolated hepatocytes

1995

Bhat, B.G.; Wang, P.; Coleman, R.A.

Biochemistry

34

11237-11244

489077

11337502

Yeast 1,3-beta-glucan synthase activity is inhibited by phytosphingosine localized to the endoplasmic reticulum

2001

Abe, M.; Nishida, I.; Minemura, M.; Qadota, H.; Seyama, Y.; Watanabe, T.; Ohya, Y.

J. Biol. Chem.

276

26923-26930

653123

11070885

Kinetic analysis of sphingoid base inhibition of yeast phosphatidate phosphatase

2000

Wu, W.I.; Carman, G.M.

Methods Enzymol.

312

373-380

657260

12821326

Molecular cloning and characterization of the alkaline ceramidase from Pseudomonas aeruginosa PA01

2003

Nieuwenhuizen, W.F.; van Leeuwen, S.; Jack, R.W.; Egmond, M.R.; Gotz, F.

Protein Expr. Purif.

30

94-104

657640

11368168

Functional identification of a DELTA8-sphingolipid desaturase from Borago officinalis

2001

Sperling, P.; Libisch, B.; Zahringer, U.; Napier, J.A.; Heinz, E.

Arch. Biochem. Biophys.

388

293-298

657892

11171153

Further characterization of DELTA8-sphingolipid desaturases from higher plants

2000

Sperling, P.; Blume, A.; Zahringer, U.; Heinz, E.

Biochem. Soc. Trans.

28

638-641

658490

12402089

Isolation and characterization of the genes encoding DELTA8-sphingolipid desaturase from Saccharomyces kluyveri and Kluyveromyces lactis

2002

Takakuwa, N.; Kinoshita, M.; Oda, Y.; Ohnishi, M.

Curr. Microbiol.

45

459-461

661329

15848761

Synthesis and evaluation of sphingoid analogs as inhibitors of sphingosine kinases

2005

Kim, J.W.; Kim, Y.W.; Inagaki, Y.; Hwang, Y.A.; Mitsutake, S.; Ryu, Y.W.; Lee, W.K.; Ha, H.J.; Park, C.S.; Igarashi, Y.

Bioorg. Med. Chem.

13

3475-3485

661509

15743396

Sphingosine kinase signalling in immune cells

2005

Kee, T.H.; Vit, P.; Melendez, A.J.

Clin. Exp. Pharmacol. Physiol.

32

153-161

661860

15585321

The role of sphingosine and ceramide kinases in inflammatory responses

2005

Baumruker, T.; Bornancin, F.; Billich, A.

Immunol. Lett.

96

175-185

663137

15665242

Arabidopsis sphingosine kinase and the effects of phytosphingosine-1-phosphate on stomatal aperture

2005

Coursol, S.; Le Stunff, H.; Lynch, D.V.; Gilroy, S.; Assmann, S.M.; Spiegel, S.

Plant Physiol.

137

724-737

674380

16584625

Sphingosine kinase: biochemical and cellular regulation and role in disease

2006

Taha, T.A.; Hannun, Y.A.; Obeid, L.M.

J. Biochem. Mol. Biol.

39

113-131

687479

17912702

Dimethylsphingosine and FTY720 inhibit the SK1 form but activate the SK2 form of sphingosine kinase from rat heart

2007

Vessey, D.A.; Kelley, M.; Zhang, J.; Li, L.; Tao, R.; Karliner, J.S.

J. Biochem. Mol. Toxicol.

21

273-279

687738

18458076

Characterization of the yeast DGK1-encoded CTP-dependent diacylglycerol kinase

2008

Han, G.S.; OHara, L.; Siniossoglou, S.; Carman, G.M.

J. Biol. Chem.

283

20443-20453

693238

18812320

Phosphatidic acid phosphatase, a key enzyme in the regulation of lipid synthesis

2009

Carman, G.M.; Han, G.

J. Biol. Chem.

284

2593-2597

728540

24366682

Identification of the substrate recognition region in the DELTA6-fatty acid and DELTA8-sphingolipid desaturase by fusion mutagenesis

2014

Song, L.; Zhang, Y.; Li, S.; Hu, J.; Yin, W.; Chen, Y.; Hao, S.; Wang, B.; Wang, R.; Hu, Z.

Planta

239

753-763

751277

30530634

Fat-regulating phosphatidic acid phosphatase a review of its roles and regulation in lipid homeostasis

2019

Carman, G.M.; Han, G.S.

J. Lipid Res.

60

2-6

752718

26635357

Substrate specificity, kinetic properties and inhibition by fumonisin B1 of ceramide synthase isoforms from Arabidopsis

2016

Luttgeharm, K.D.; Cahoon, E.B.; Markham, J.E.

Biochem. J.

473

593-603

753522

11060777

Antifungals targeted to sphingolipid synthesis Focus on inositol phosphorylceramide synthase

2000

Georgopapadakou, N.

Expert Opin. Investig. Drugs

9

1787-1796

756124

29625159

The revelation of selective sphingolipid pathway inhibition mechanism on fumonisin toxin binding to ceramide synthases in susceptible organisms and survival mechanism in resistant species

2018

Sharma, S.; Ahmed, M.; Akhter, Y.

Biochimie

149

41-50

756397

29425496

The role of ceramide synthases in the pathogenicity of Cryptococcus neoformans

2018

Munshi, M.; Gardin, J.; Singh, A.; Luberto, C.; Rieger, R.; Bouklas, T.; Fries, B.; Del Poeta, M.

Cell Rep.

22

1392-1400

757289

31164445

Yeast ceramide synthases, Lag1 and Lac1, have distinct substrate specificity

2019

Megyeri, M.; Prasad, R.; Volpert, G.; Sliwa-Gonzalez, A.; Haribowo, A.; Aguilera-Romero, A.; Riezman, H.; Barral, Y.; Futerman, A.; Schuldiner, M.

J. Cell Sci.

132

jcs228411

Links to other databases for phytosphingosine

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Show Links (1 entry)

ChEBI

PubChem