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

General Information of Drug (ID: DR2246)
Drug Name
BE-14348A
Synonyms
Naringenin; BE-14348A; FTVWIRXFELQLPI-UHFFFAOYSA-N; Flavanone, 4',5,7-trihydroxy-; NARIGENIN; Naringenine; Salipurol; naringenin; naringetol; salipurpol; ( inverted exclamation markA)-Naringenin; (+/-)-Naringenin; (-)-Naringenin; (S)-Naringenin; 4',5,7-Trihydroxyflavanone; 4',7-Trihydroxyflavanone; 480-41-1; 5,7,4'-Trihydroxyflavanone; 5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one; 67604-48-2; 93602-28-9; AK122638; CHEBI:50202; CHEMBL32571; MFCD00006844; MLS000028739; MLS000738094; NSC 11855; NSC 34875; NSC11855; NSC34875; SMR000059039
Indication Viral hepatitis [ICD11: 1E51] Phase 1 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 272.25 Topological Polar Surface Area 87
Heavy Atom Count 20 Rotatable Bond Count 1
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
932
ChEBI ID
CHEBI:50202
CAS Number
480-41-1
TTD Drug ID
D02ABO
Formula
C15H12O5
Canonical SMILES
C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O
InChI
1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2/t13-/m0/s1
InChIKey
FTVWIRXFELQLPI-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
3-(4-Hydroxyphenyl) propionic acid DM003390
10394
Unclear 1 [6]
5,7-Dihydroxychromone DM003397
5281343
Unclear 1 [4]
Apigenin DM003396
5280443
Oxidation - Dehydrogenation 1 [4]
Eriodictyol DM003394
440735
Oxidation - Hydrolyzationn 1 [4]
Naringenin-O-glucuronides DM003398 N. A. Conjugation - Glucuronidation 1 [4]
Phloroglucinol DM003399
359
Unclear 1 [6]
(4-Hydroxyphenyl) acetic acid DM001229
127
Unclear 2 [6]
3-Phenylpropionic acid DM003391
107
Unclear 2 [6]
Hesperetin DM003395
72281
Conjugation - Methylationn 2 [4]
Midostaurin Metabolite P6 DM001360
243
Unclear 3 [6]
4-Hydroxyhippuric acid DM003392
151012
Unclear 4 [6]
Midostaurin Metabolite P6B DM001361
464
Unclear 4 [6]
⏷ Show the Full List of 12  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003833 BE-14348A 3-(4-Hydroxyphenyl) propionic acid Unclear Unclear [6]
MR003839 BE-14348A Eriodictyol Oxidation - Hydrolyzationn CYP1A2 ... [4]
MR003841 BE-14348A Apigenin Oxidation - Dehydrogenation CYP2C9 ... [4]
MR003842 BE-14348A 5,7-Dihydroxychromone Unclear CYP2C9 [4]
MR003843 BE-14348A Naringenin-O-glucuronides Conjugation - Glucuronidation Unclear [4]
MR003844 BE-14348A Phloroglucinol Unclear Unclear [6]
MR003834 3-(4-Hydroxyphenyl) propionic acid 3-Phenylpropionic acid Unclear Unclear [6]
MR003838 3-(4-Hydroxyphenyl) propionic acid (4-Hydroxyphenyl) acetic acid Unclear Unclear [6]
MR003840 Eriodictyol Hesperetin Conjugation - Methylationn Unclear [4]
MR003835 3-Phenylpropionic acid Benzoic acid Unclear Unclear [6]
MR003836 Benzoic acid 4-Hydroxyhippuric acid Unclear Unclear [6]
MR003837 Benzoic acid Hippuric acid Unclear Unclear [6]
⏷ Show the Full List of 12 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 105D7 (cyp105) DME1233 Streptomyces avermitilis
CYP28_STRAW
1.14.15.11
[2] , [3]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[4]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[4]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[4]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[4]
Unclear metabolic mechanism (DME-unclear) DME1257 Bifidobacterium longum Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1277 Lactobacillus rhamnosus Not Available Not Available [5]
⏷ Show the Full List of 9  DME(s)
References
1 ClinicalTrials.gov (NCT01091077) A Pilot Study of the Grapefruit Flavonoid Naringenin for HCV Infection
2 The metagenome of Caracolus marginella gut microbiome using culture independent approaches and shotgun sequencing. Data Brief. 2017 Nov 22;16:501-505.
3 Hydroxylation of Compactin (ML-236B) by CYP105D7 (SAV_7469) from Streptomyces avermitilis. J Microbiol Biotechnol. 2017 May 28;27(5):956-964.
4 Pharmacokinetics and Metabolism of Naringin and Active Metabolite Naringenin in Rats, Dogs, Humans, and the Differences Between Species
5 Catabolism of citrus flavanones by the probiotics Bifidobacterium longum and Lactobacillus rhamnosus. Eur J Nutr. 2018 Feb;57(1):231-242.
6 High gastrointestinal permeability and local metabolism of naringenin: influence of antibiotic treatment on absorption and metabolism

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