Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR3191)
Drug Name
Phenylbutyrate
Synonyms
Benzenebutyric acid; Phenyl butanoate; Phenyl butyrate; HDInhib_000004; Butanoic acid, phenyl ester; Butyric acid, phenyl ester; FR-2080; Gamma-Phenylbutyric acid; Omega-Phenylbutanoic acid; GAMMA-PHENYL-BUTYRIC ACID; Butyric acid, 4-phenyl-(8CI); 1-Phenylbutyric acid; 4-PHENYL-BUTANOIC ACID; 4-PHENYLBUTYRIC ACID; 4-Phenylbutanoic acid; 4-phenylbutans; 4-phenylbutyrate
Indication Phenylketonuria [ICD11: 5C50] Phase 2 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 164.2 Topological Polar Surface Area 37.3
Heavy Atom Count 12 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
4775
ChEBI ID
CHEBI:41500
CAS Number
1821-12-1
TTD Drug ID
D0B7CH
Formula
C10H12O2
Canonical SMILES
C1=CC=C(C=C1)CCCC(=O)O
InChI
InChI=1S/C10H12O2/c11-10(12)8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8H2,(H,11,12)
InChIKey
OBKXEAXTFZPCHS-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Phenybutyryl-CoA DM018730 N. A. Unclear - Unclear 1 [4]
Phenylbutenoyl-CoA DM005180 N. A. Unclear - Unclear 2 [4]
Beta-Hydroxyphenylbutyryl-CoA DM005181 N. A. Unclear - Unclear 3 [4]
Beta-Ketophenylbutyryl-CoA DM005182 N. A. Unclear - Unclear 4 [4]
Acetyl Coenzyme A DM003095
444493
Unclear - Unclear 5 [4]
Phenylacetyl-CoA DM005183
165620
Unclear - Unclear 5 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013766 Phenylbutyrate Phenybutyryl-CoA Unclear - Unclear Unclear [4]
MR013767 Phenybutyryl-CoA Phenylbutenoyl-CoA Unclear - Unclear Unclear [4]
MR013768 Phenylbutenoyl-CoA Beta-Hydroxyphenylbutyryl-CoA Unclear - Unclear ECHS1 [4]
MR013769 Beta-Hydroxyphenylbutyryl-CoA Beta-Ketophenylbutyryl-CoA Unclear - Unclear HSDB [4]
MR013770 Beta-Ketophenylbutyryl-CoA Phenylacetyl-CoA Unclear - Unclear Unclear [4]
MR013771 Beta-Ketophenylbutyryl-CoA Acetyl-CoA Unclear - Unclear ACAT2 [4]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
(R)-beta-hydroxybutyrate dehydrogenase (BDH2) DMEN776 Homo sapiens
DHRS6_HUMAN
1.1.1.-
[2]
3-ketoacyl-CoA thiolase (CKAT) DMEN774 Homo sapiens Not Available Not Available [2]
3-MG-CoA hydratase (AUH) DMEN263 Homo sapiens
AUHM_HUMAN
4.2.1.18
[3]
Acyl-CoA hydrolase (ACAA2) DMEN775 Homo sapiens
THIM_HUMAN
2.3.1.16
[2]
acyl-CoA-L-glutamine N-acyltransferase (GLYATL1) DMEN777 Homo sapiens
GLYL1_HUMAN
2.3.1.68
[2]
Enoyl-CoA hydratase (ECHS1) DMEN259 Homo sapiens
ECHM_HUMAN
4.2.1.17
[3]
glycine N-acylase (GLYNA) DMEN778 Homo sapiens Not Available Not Available [2]
Long-chain 3-hydroxyacyl-CoA dehydrogenase (LCHAD) DMEN267 Homo sapiens Not Available Not Available [3]
long-chain 3-ketoacyl-CoA thiolas (LCKAT) DMEN773 Homo sapiens Not Available Not Available [3]
long-chain 3-ketoacyl-CoA thiolas (LCKAT) DMEN773 Homo sapiens Not Available Not Available [2]
Long-chain enoyl-CoA hydratase (HADHA) DMEN265 Homo sapiens
ECHA_HUMAN
1.1.1.211
[3]
S-(hydroxymethyl)glutathione dehydrogenase (adh) DME1249 Vibrio cholerae
A0A0A7DS01_VIBCL
1.1.1.284
[2]
UDP-glucuronyltransferase (UGT) DMEN064 . Not Available Not Available [2]
⏷ Show the Full List of 13  DME(s)
References
1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 8480).
2 New secondary metabolites of phenylbutyrate in humans and rats
3 Identification of enzymes involved in oxidation of phenylbutyrate
4 Phase 2 comparison of a novel ammonia scavenging agent with sodium phenylbutyrate in patients with urea cycle disorders: safety, pharmacokinetics and ammonia control

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.