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Literature summary extracted from

  • Merkler, D.J.; Asser, A.S.; Baumgart, L.E.; Carballo, N.; Carpenter, S.E.; Chew, G.H.; Cosner, C.C.; Dusi, J.; Galloway, L.C.; Lowe, A.B.; Lowe, E.W.; King, L.; Kendig, R.D.; Kline, P.C.; Malka, R.; Merkler, K.A.; McIntyre, N.R.; Romero, M.; Wilcox, B.J.; Owen, T.C.
    Substituted hippurates and hippurate analogs as substrates and inhibitors of peptidylglycine alpha-hydroxylating monooxygenase (PHM) (2008), Bioorg. Med. Chem., 16, 10061-10074.
    View publication on PubMedView publication on EuropePMC

Application

EC Number Application Comment Organism
1.14.17.3 medicine PHM is a potential target for the development of inhibitors as drugs for the teratment of human disease Homo sapiens
1.14.17.3 medicine PHM is a potential target for the development of inhibitors as drugs for the treatment of human disease Rattus norvegicus
1.14.17.3 medicine PHM is a potential target for the development of insecticides Blattella germanica

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.14.17.3
-
 Rattus norvegicus

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.14.17.3 (CBZ-hydrazido)glycine
-
 Rattus norvegicus
1.14.17.3 (nicotinamidomethyl)phosphonic acid
-
 Rattus norvegicus
1.14.17.3 (S)-N-CBZ-4-amino-2-hydroxybutyric acid
-
 Rattus norvegicus
1.14.17.3 3-benzoylpropionic acid
-
 Rattus norvegicus
1.14.17.3 6-O-palmitoyl-L-ascorbate
-
 Rattus norvegicus
1.14.17.3 glutathione ethyl ester
-
 Rattus norvegicus
1.14.17.3 N,S-dibenzoyl-L-cysteine
-
 Rattus norvegicus
1.14.17.3 N-(benzoyl)-D-serine
-
 Rattus norvegicus
1.14.17.3 N-(thiobenzoyl)-(D,L)-alanine
-
 Rattus norvegicus
1.14.17.3 N-benzylglycine
-
 Rattus norvegicus
1.14.17.3 N-phenylthiohydantoic acid
-
 Rattus norvegicus
1.14.17.3 O-(phenylcarbamoyl)glycolic acid
-
 Rattus norvegicus
1.14.17.3 O-benzamidoglycolic acid
-
 Rattus norvegicus
1.14.17.3 Pro-Leu-Gly hydroxamic acid
-
 Rattus norvegicus
1.14.17.3 S-(2-phenylthioacetyl)thioglycolic acid
-
 Blattella germanica
1.14.17.3 S-(2-phenylthioacetyl)thioglycolic acid
-
 Homo sapiens
1.14.17.3 S-(2-phenylthioacetyl)thioglycolic acid
-
 Rattus norvegicus
1.14.17.3 S-(3-phenylthiopropionyl)thioglycolic acid
-
 Blattella germanica
1.14.17.3 S-(3-phenylthiopropionyl)thioglycolic acid
-
 Rattus norvegicus
1.14.17.3 S-(4-methylthiobenzoyl)thioglycolic acid
-
 Blattella germanica
1.14.17.3 S-(4-methylthiobenzoyl)thioglycolic acid
-
 Rattus norvegicus
1.14.17.3 S-(4-methylthiobenzoyl)thioglycolic acid ethyl ester
-
 Rattus norvegicus
1.14.17.3 S-(phenylthiocarbamoyl)-3-mercaptopropionic acid
-
 Blattella germanica
1.14.17.3 S-(phenylthiocarbamoyl)-3-mercaptopropionic acid
-
 Rattus norvegicus
1.14.17.3 S-(phenylthiocarbamoyl)thioglycolic acid
-
 Blattella germanica
1.14.17.3 S-(phenylthiocarbamoyl)thioglycolic acid
-
 Rattus norvegicus
1.14.17.3 S-(thiobenzoyl)-(R,S)-thiolactic acid
-
 Rattus norvegicus
1.14.17.3 S-(thiobenzoyl)-4-mercapto-4-cyanopentanoic acid
-
 Rattus norvegicus
1.14.17.3 S-(thiobenzoyl)thioglycolic acid
-
 Blattella germanica
1.14.17.3 S-(thiobenzoyl)thioglycolic acid
-
 Rattus norvegicus
1.14.17.3 S-(thiolauroyl)thioglycolic acid
-
 Rattus norvegicus
1.14.17.3 S-phenylmercaptoacetic acid
-
 Blattella germanica
1.14.17.3 S-phenylmercaptoacetic acid
-
 Rattus norvegicus
1.14.17.3 Salicylhydroxamic acid
-
 Rattus norvegicus

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.14.17.3 0.024
-
 phenylthioacetylglycine apparent KM Rattus norvegicus
1.14.17.3 0.031
-
 N-dansyl-Tyr-Val-D-Ala apparent KM Rattus norvegicus
1.14.17.3 0.036
-
 2-pyridylmercaptoacetylglycine apparent KM Rattus norvegicus
1.14.17.3 0.038
-
 3-phenylthiopropionylglycine apparent KM Rattus norvegicus
1.14.17.3 0.051
-
 6-phenylhexanoylglycine apparent KM Rattus norvegicus
1.14.17.3 0.059
-
 N-[(benzylmercapto)carbonyl]glycine apparent KM Rattus norvegicus
1.14.17.3 0.078
-
 hippuryl-Gly apparent KM Rattus norvegicus
1.14.17.3 0.1
-
 8-phenyloctanoylglycine apparent KM Rattus norvegicus
1.14.17.3 0.11
-
 4-nitrobenzoyl-Gly-Gly apparent KM Rattus norvegicus
1.14.17.3 0.15
-
 5-phenylpentanoylglycine apparent KM Rattus norvegicus
1.14.17.3 0.16
-
 N-(Phenylacetyl)glycine apparent KM Rattus norvegicus
1.14.17.3 0.16
-
 4-phenylbutyrylglycine apparent KM Rattus norvegicus
1.14.17.3 0.19
-
 phenylmercaptoacetylglycine apparent KM Rattus norvegicus
1.14.17.3 0.22
-
 2-propylmercaptoacetylglycine apparent KM Rattus norvegicus
1.14.17.3 0.23
-
 cinnamoylglycine apparent KM Rattus norvegicus
1.14.17.3 0.28
-
 isocaproylglycine apparent KM Rattus norvegicus
1.14.17.3 0.3
-
 3-indolylacetylglycine apparent KM Rattus norvegicus
1.14.17.3 0.3
-
 tBOC-Gly-Gly apparent KM Rattus norvegicus
1.14.17.3 0.31
-
 L-pyroglutamyl-Gly apparent KM Rattus norvegicus
1.14.17.3 0.31
-
 hippuryl-Gly-Gly apparent KM Rattus norvegicus
1.14.17.3 0.36
-
 phenylhydantoic acid apparent KM Rattus norvegicus
1.14.17.3 0.42
-
 chloroacetyl-Gly-Gly apparent KM Rattus norvegicus
1.14.17.3 0.47
-
 4-nitrohippuric acid apparent KM Rattus norvegicus
1.14.17.3 0.52
-
 4-bromohippuric acid apparent KM Rattus norvegicus
1.14.17.3 0.59
-
 CBZ-glycine apparent KM Rattus norvegicus
1.14.17.3 0.62
-
 4-chlorohippuric acid apparent KM Rattus norvegicus
1.14.17.3 0.77
-
 4-trifluoromethylhippuric acid apparent KM Rattus norvegicus
1.14.17.3 0.82
-
 4-methoxyhippuric acid apparent KM Rattus norvegicus
1.14.17.3 0.86
-
 2-hydroxyhippuric acid apparent KM Rattus norvegicus
1.14.17.3 0.9
-
 N-[(2-phenylcyclopropyl)carbonyl]glycine apparent KM Rattus norvegicus
1.14.17.3 0.94
-
 hydrocinnamoylglycine apparent KM Rattus norvegicus
1.14.17.3 1.2
-
 4-ethylhippuric acid apparent KM Rattus norvegicus
1.14.17.3 1.2
-
 4-propylhippuric acid apparent KM Rattus norvegicus
1.14.17.3 1.2
-
 3-(2-furyl)acryloylglycine apparent KM Rattus norvegicus
1.14.17.3 1.3
-
 hippuric acid apparent KM Rattus norvegicus
1.14.17.3 1.4
-
 2-aminohippuric acid apparent KM Rattus norvegicus
1.14.17.3 1.4
-
 3-methylhippuric acid apparent KM Rattus norvegicus
1.14.17.3 1.5
-
 acetyl-Gly-Gly apparent KM Rattus norvegicus
1.14.17.3 1.6
-
 N-(2-thienylcarbonyl)glycine apparent KM Rattus norvegicus
1.14.17.3 1.7
-
 4-hydroxyhippuric acid apparent KM Rattus norvegicus
1.14.17.3 1.8
-
 4-methylhippuric acid apparent KM Rattus norvegicus
1.14.17.3 1.9
-
 nicotinuric acid apparent KM Rattus norvegicus
1.14.17.3 2.2
-
 3-chlorohippuric acid apparent KM Rattus norvegicus
1.14.17.3 2.6
-
 4-aminohippuric acid apparent KM Rattus norvegicus
1.14.17.3 2.7
-
 N-(2-furoyl)glycine apparent KM Rattus norvegicus
1.14.17.3 3.4
-
 2-iodohippuric acid apparent KM Rattus norvegicus
1.14.17.3 3.7
-
 tBOC-Gly apparent KM Rattus norvegicus
1.14.17.3 4.1
-
 N-(alpha-methylhydrocinnamoyl)glycine apparent KM Rattus norvegicus
1.14.17.3 4.3
-
 2-methylhippuric acid apparent KM Rattus norvegicus
1.14.17.3 9.3
-
 N-acetylglycine apparent KM Rattus norvegicus
1.14.17.3 19
-
 2,6-difluorohippuric acid apparent KM Rattus norvegicus
1.14.17.3 35
-
 CBZ-D-alanine apparent KM Rattus norvegicus
1.14.17.3 84
-
 benzoyl-D-alanine apparent KM Rattus norvegicus
1.14.17.3 1400
-
 acetyl-D-alanine apparent KM Rattus norvegicus

Organism

EC Number Organism UniProt Comment Textmining
1.14.17.3 Blattella germanica
-
-
-
1.14.17.3 Homo sapiens
-
-
-
1.14.17.3 Rattus norvegicus P14925
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.14.17.3
-
 Blattella germanica
1.14.17.3
-
 Rattus norvegicus

Source Tissue

EC Number Source Tissue Comment Organism Textmining
1.14.17.3 DU-145 cell
-
 Homo sapiens
-
1.14.17.3 medullary thyroid carcinoma cell
-
 Rattus norvegicus
-

Specific Activity [micromol/min/mg]

EC Number Specific Activity Minimum [µmol/min/mg] Specific Activity Maximum [µmol/min/mg] Comment Organism
1.14.17.3 0.01
-
 N-dansyl-Tyr-Val-Gly Blattella germanica
1.14.17.3 3
-
 O2 Rattus norvegicus

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.17.3 2,6-difluorohippuric acid + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 2-aminohippuric acid + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 2-hydroxyhippuric acid + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 2-iodohippuric acid + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 2-methylhippuric acid + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 2-propylmercaptoacetylglycine + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 2-pyridylmercaptoacetylglycine + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 3-(2-furyl)acryloylglycine + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 3-chlorohippuric acid + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 3-indolylacetylglycine + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 3-methylhippuric acid + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 3-phenylthiopropionylglycine + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 4-aminohippuric acid + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 4-bromohippuric acid + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 4-chlorohippuric acid + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 4-ethylhippuric acid + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 4-hydroxyhippuric acid + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 4-methoxyhippuric acid + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 4-methylhippuric acid + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 4-nitrobenzoyl-Gly-Gly + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 4-nitrohippuric acid + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 4-phenylbutyrylglycine + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 4-propylhippuric acid + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 4-trifluoromethylhippuric acid + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 5-phenylpentanoylglycine + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 6-phenylhexanoylglycine + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 8-phenyloctanoylglycine + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 acetyl-D-alanine + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 acetyl-Gly-Gly + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 benzoyl-D-alanine + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 CBZ-D-alanine + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 CBZ-glycine + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 chloroacetyl-Gly-Gly + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 cinnamoylglycine + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 hippuric acid + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 hippuryl-Gly + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 hippuryl-Gly-Gly + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 hydrocinnamoylglycine + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 isocaproylglycine + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 L-pyroglutamyl-Gly + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 N-(2-furoyl)glycine + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 N-(2-thienylcarbonyl)glycine + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 N-(alpha-methylhydrocinnamoyl)glycine + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 N-(phenylacetyl)glycine + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 N-acetylglycine + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 N-Dan-Tyr-Val-Gly + ascorbate + O2 the product is unstable and dismutates to N-Dan-Tyr-Val-NH2 and glyoxylate (EC4.3.2.5) Blattella germanica N-Dan-Tyr-Val-2-hydroxyglycine + dehydroascorbate + H2O
-
 ?
1.14.17.3 N-dansyl-Tyr-Val-D-Ala + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 N-[(2-phenylcyclopropyl)carbonyl]glycine + ascorbate + O2
-
 Rattus norvegicus N-[(2-phenylcyclopropyl)carbonyl]-2-hydroxyglycine + dehydroascorbate + H2O
-
 r
1.14.17.3 N-[(benzylmercapto)carbonyl]glycine + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 N-[(phenylcyclopropyl)carbonyl]glycine + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 nicotinuric acid + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 phenylhydantoic acid + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 phenylmercaptoacetylglycine + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 phenylthioacetylglycine + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 tBOC-Gly + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?
1.14.17.3 tBOC-Gly-Gly + ascorbate + O2
-
 Rattus norvegicus ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.14.17.3 PAM
-
 Blattella germanica
1.14.17.3 PAM
-
 Rattus norvegicus
1.14.17.3 peptidylglycine alpha-hydroxylating monooxygenase
-
 Homo sapiens
1.14.17.3 peptidylglycine alpha-hydroxylating monooxygenase
-
 Blattella germanica
1.14.17.3 peptidylglycine alpha-hydroxylating monooxygenase
-
 Rattus norvegicus
1.14.17.3 PHM
-
 Homo sapiens
1.14.17.3 PHM
-
 Blattella germanica
1.14.17.3 PHM
-
 Rattus norvegicus
1.14.17.3 type A PAM
-
 Rattus norvegicus

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.14.17.3 37
-
-
 Blattella germanica
1.14.17.3 37
-
 activity assay Rattus norvegicus

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.14.17.3 6
-
-
 Blattella germanica
1.14.17.3 6
-
 activity assay Rattus norvegicus

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
1.14.17.3 0.00054
-
 S-(thiolauroyl)thioglycolic acid Ki,s Rattus norvegicus
1.14.17.3 0.0026
-
 S-(phenylthiocarbamoyl)-3-mercaptopropionic acid Ki,s Rattus norvegicus
1.14.17.3 0.0035
-
 S-(4-methylthiobenzoyl)thioglycolic acid Ki,s Rattus norvegicus
1.14.17.3 0.0057
-
 S-(thiobenzoyl)-4-mercapto-4-cyanopentanoic acid Ki,s Rattus norvegicus
1.14.17.3 0.0072
-
 N-(thiobenzoyl)-(D,L)-alanine Ki,s Rattus norvegicus
1.14.17.3 0.0079
-
 S-(2-phenylthioacetyl)thioglycolic acid Ki,s Rattus norvegicus
1.14.17.3 0.0086
-
 S-(phenylthiocarbamoyl)thioglycolic acid Ki,s Rattus norvegicus
1.14.17.3 0.0094
-
 S-(3-phenylthiopropionyl)thioglycolic acid Ki,s Rattus norvegicus
1.14.17.3 0.035
-
 6-O-palmitoyl-L-ascorbate Ki,s Rattus norvegicus
1.14.17.3 0.039
-
 S-(thiobenzoyl)thioglycolic acid Ki,s Rattus norvegicus
1.14.17.3 0.054
-
 O-(phenylcarbamoyl)glycolic acid Ki,s Rattus norvegicus
1.14.17.3 0.058
-
 S-(thiobenzoyl)-(R,S)-thiolactic acid Ki,s Rattus norvegicus
1.14.17.3 0.066
-
 glutathione ethyl ester Ki,s Rattus norvegicus
1.14.17.3 0.069
-
 N,S-dibenzoyl-L-cysteine Ki,s Rattus norvegicus
1.14.17.3 0.11
-
 N-phenylthiohydantoic acid Ki,s Rattus norvegicus
1.14.17.3 0.11
-
 S-(4-methylthiobenzoyl)thioglycolic acid ethyl ester Ki,s Rattus norvegicus
1.14.17.3 0.3
-
 Salicylhydroxamic acid Ki,s Rattus norvegicus
1.14.17.3 0.38
-
 S-phenylmercaptoacetic acid Ki,s Rattus norvegicus
1.14.17.3 1
-
 O-benzamidoglycolic acid Ki,s Rattus norvegicus
1.14.17.3 1
-
 Pro-Leu-Gly hydroxamic acid Ki,s Rattus norvegicus
1.14.17.3 1.4
-
 (S)-N-CBZ-4-amino-2-hydroxybutyric acid Ki,s Rattus norvegicus
1.14.17.3 1.5
-
 N-(benzoyl)-D-serine Ki,s Rattus norvegicus
1.14.17.3 2.9
-
 3-benzoylpropionic acid Ki,s Rattus norvegicus
1.14.17.3 7.9
-
 (CBZ-hydrazido)glycine Ki,s Rattus norvegicus
1.14.17.3 18
-
 N-benzylglycine Ki,s Rattus norvegicus
1.14.17.3 75
-
 (nicotinamidomethyl)phosphonic acid Ki,s, larger than 75 Rattus norvegicus