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

General Information of Drug (ID: DR2357)
Drug Name
BRN-0183227
Synonyms
BRN 0183227; CHEBI:5070; CHEMBL274318; EINECS 207-654-8; MFCD00006841; MLS002667384; NSC 50393; NSC-50393; NSC50393; FLAVANONE; ZONYXWQDUYMKFB-UHFFFAOYSA-N; (-)-Flavanone; 2,3-Dihydro-2-phenyl-4H-1-benzopyran-4-one; 2,3-Dihydro-2-phenyl-4H-benzopyran-4-one; 2,3-Dihydroflavone; 2-Phenyl-2,3-dihydro-4H-chromen-4-one; 2-Phenyl-4-chromanone; 2-Phenyl-chroman-4-one; 2-Phenylchroman-4-one; 2-phenyl-2,3-dihydrochromen-4-one; 2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one; 4-Flavanone; 487-26-3; 4H-1-Benzopyran-4-one, 2,3-dihydro-2-phenyl-; Flavanone
Indication Acute coronary syndrome [ICD11: BA4Z] Phase 1 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 224.25 Topological Polar Surface Area 26.3
Heavy Atom Count 17 Rotatable Bond Count 1
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
10251
PubChem SID
4028 ; 102205 ; 619227 ; 3134927 ; 4512170 ; 8138274 ; 8157393 ; 10523909 ; 10589599 ; 11341995 ; 11362178 ; 11362915 ; 11365477 ; 11368039 ; 11371267 ; 11375249 ; 11376201 ; 11408604 ; 11483925 ; 11487580 ; 11488021 ; 11489990 ; 11493460 ; 11493895 ; 14717855 ; 15043641 ; 24295177 ; 24846563 ; 26613018 ; 26679643 ; 26749819 ; 29204140 ; 29228771 ; 47217216 ; 47515755 ; 47885852 ; 48110894 ; 48259673 ; 48421824 ; 49969977 ; 50107717 ; 50107718 ; 52951290 ; 53787071 ; 56367296 ; 57326076 ; 85209501 ; 85730926 ; 85789144 ; 85789390
ChEBI ID
ChEBI:5070
CAS Number
487-26-3
TTD Drug ID
D0B4VE
Formula
C15H12O2
Canonical SMILES
C1C(OC2=CC=CC=C2C1=O)C3=CC=CC=C3
InChI
1S/C15H12O2/c16-13-10-15(11-6-2-1-3-7-11)17-14-9-5-4-8-12(13)14/h1-9,15H,10H2
InChIKey
ZONYXWQDUYMKFB-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
Naringenin DM003408
439246
Oxidation - Hydrolyzationn 1 [4]
Isosakuranetin DM003409
160481
Unclear 2 [4]
Naringenin-4',7-sulfo-O-glucuronide DM003411 N. A. Unclear 2 [3]
Naringenin-4'-O-glucuronide DM003412
91312540
Unclear 2 [3]
Naringenin-7-O-glucuronide DM003413
51136360
Unclear 2 [3]
Hesperetin DM003395
72281
Oxidation - Hydrolyzationn 3 [4]
Hesperetin-sulfo-O-glucuronide DM003410 N. A. Unclear 4 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003855 BRN-0183227 Naringenin Oxidation - Hydrolyzationn Unclear [4]
MR003856 Naringenin Isosakuranetin Unclear Unclear [4]
MR003859 Naringenin Naringenin-4',7-sulfo-O-glucuronide Unclear Unclear [3]
MR003860 Naringenin Naringenin-4'-O-glucuronide Unclear Unclear [3]
MR003861 Naringenin Naringenin-7-O-glucuronide Unclear Unclear [3]
MR003857 Isosakuranetin Hesperetin Oxidation - Hydrolyzationn Unclear [4]
MR003858 Hesperetin Hesperetin-sulfo-O-glucuronide Unclear UGT1A1 ... [3]
⏷ Show the Full List of 7 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Biphenyl dioxygenase (bphC) DME1009 Pseudomonas furukawaii
BPHC_PSEFK
1.13.11.39
[2]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 1A8 (UGT1A8) DME0064 Homo sapiens
UD18_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[3]
References
1 ClinicalTrials.gov (NCT00983086) Effects of Consumption of Orange Juice on Vascular Protection and Immune Function: Clinical Study on the Specific Contribution of Citrus Flavanones
2 Flavonoids biotransformation by bacterial non-heme dioxygenases, biphenyl and naphthalene dioxygenase. Appl Microbiol Biotechnol. 2011 Jul;91(2):219-28.
3 Stratification of Volunteers According to Flavanone Metabolite Excretion and Phase II Metabolism Profile after Single Doses of 'Pera' Orange and 'Moro' Blood Orange Juices
4 Flavanone metabolism in healthy and tumor-bearing rats

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