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Literature summary for 1.14.17.3 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

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

Cloned(Commentary)

Cloned (Comment) Organism
-
Rattus norvegicus

Inhibitors

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

KM Value [mM]

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

Organism

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

Purification (Commentary)

Purification (Comment) Organism
-
Blattella germanica
-
Rattus norvegicus

Source Tissue

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

Specific Activity [micromol/min/mg]

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

Substrates and Products (Substrate)

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

Synonyms

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

Temperature Optimum [°C]

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

pH Optimum

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

Ki Value [mM]

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