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

General Information of Drug (ID: DR2108)
Drug Name
L-phenylalanine
Synonyms
Phenylalanine (VAN); Phenylalaninum [Latin]; Alanine, 3-phenyl-; Alanine, phenyl-, L-; Antibiotic FN 1636; Fenilalanina [Spanish]; H-Phe-OH; L-Alanine, 3-phenyl-; beta-Phenyl-L-alanine; phenylalanine; L-Alanine, phenyl-; L-Antibiotic FN 1636; L-phenylalanine; (2S)-2-amino-3-phenylpropanoic acid; (L)-Phenylalanine; (S)-2-Amino-3-phenylpropanoic acid; (S)-2-Amino-3-phenylpropionic acid; (S)-Phenylalanine; (S)-alpha-Amino-beta-phenylpropionic acid; (S)-alpha-Aminohydrocinnamic acid; 3-Phenyl-L-alanine; 3-Phenylalanine; 63-91-2
Indication Phenylketonuria [ICD11: 5C50] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 165.19 Topological Polar Surface Area 63.3
Heavy Atom Count 12 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
6140
PubChem SID
3379 ; 584667 ; 822460 ; 824902 ; 832928 ; 838754 ; 841094 ; 3134198 ; 4252550 ; 6436530 ; 7847089 ; 7889851 ; 8144203 ; 8153851 ; 10531434 ; 11457628 ; 11459655 ; 11528323 ; 11532528 ; 14710668 ; 15219430 ; 24770335 ; 24770338 ; 24770342 ; 24887247 ; 24898274 ; 24898657 ; 24898971 ; 24901797 ; 26651814 ; 26702643 ; 26748791 ; 26748792 ; 26753740 ; 29225143 ; 46391851 ; 46393329 ; 46505708 ; 50107465 ; 57323218 ; 57578102 ; 57652717 ; 57654567 ; 57655097 ; 78164833 ; 81044023 ; 81044025 ; 81044569 ; 81067307 ; 81067312
ChEBI ID
ChEBI:17295
CAS Number
63-91-2
TTD Drug ID
D0R1CR
Formula
C9H11NO2
Canonical SMILES
C1=CC=C(C=C1)CC(C(=O)O)N
InChI
1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/t8-/m0/s1
InChIKey
COLNVLDHVKWLRT-QMMMGPOBSA-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
Tyrosine DM003105
6057
Unclear 1 [4]
Levodopa DM002603
6047
Unclear 2 [4]
3-(3',4'-dihydroxyphenyl)propionic acid DM002604
348154
Unclear 3 [4]
DOPP DM002608
165198
Unclear 3 [4]
DOPL DM002605
439435
Unclear 4 [4]
(3,4-Dihydroxyphenyl)acetic acid DM000280
547
Unclear 5 [4]
Protocatechuate DM002607
72
Unclear 6 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003502 L-phenylalanine L-Tyrosine Unclear Unclear [4]
MR003503 L-Tyrosine DOPA Unclear Unclear [4]
MR003504 DOPA 3,4-dihydroxyphenylpropionic acid(DPPA) Unclear Unclear [4]
MR003508 DOPA DOPP Unclear Unclear [4]
MR003505 3,4-dihydroxyphenylpropionic acid(DPPA) DOPL Unclear Unclear [4]
MR003509 DOPP DOPL Unclear Unclear [4]
MR003506 DOPL 3,4-dihydroxyphenylacetic acid Unclear Unclear [4]
MR003507 3,4-dihydroxyphenylacetic acid 3,4-Dihydroxybenzoic acid Unclear Unclear [4]
⏷ Show the Full List of 8 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Phenylalanine--tRNA ligase mitochondrial (FARS2) DME0491 Homo sapiens
SYFM_HUMAN
6.1.1.20
[2]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1259 Intestinibacter bartlettii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1267 Anaerobutyricum hallii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1366 Bacteroides eggerthii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1376 Bacteroides ovatus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1445 Parabacteroides distasonis Not Available Not Available [3]
⏷ Show the Full List of 8  DME(s)
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Phenylalanine--tRNA ligase mitochondrial (FARS2) DME0491 Km = 0.033 microM
SYFM_HUMAN
[2]
References
1 ClinicalTrials.gov (NCT03788343) Phenylalanine and Its Impact on Cognition.
2 Expression and characterization of a human mitochondrial phenylalanyl-tRNA synthetase. J Mol Biol. 1999 May 14;288(4):567-77.
3 Major phenylpropanoid-derived metabolites in the human gut can arise from microbial fermentation of protein. Mol Nutr Food Res. 2013 Mar;57(3):523-35.
4 Catabolism of L-phenylalanine and L-tyrosine by Rhodobacter sphaeroides OU5 occurs through 3,4-dihydroxyphenylalanine Res Microbiol. 2007 Jul-Aug;158(6):506-11. doi: 10.1016/j.resmic.2007.04.008.

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