Details of the Drug

General Information of Drug (ID: DMHAZLM)

Drug Name
NARINGENIN
Synonyms
naringenin; 5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one; 67604-48-2; 4',5,7-Trihydroxyflavanone; Naringenine; (+/-)-Naringenin; naringetol; 480-41-1; salipurpol; (-)-Naringenin; NARIGENIN; Salipurol; 5,7,4'-Trihydroxyflavanone; 93602-28-9; (S)-Naringenin; BE-14348A; NSC 34875; ( inverted exclamation markA)-Naringenin; CHEMBL32571; MLS000738094; MLS000028739; CHEBI:50202; Flavanone, 4',5,7-trihydroxy-; FTVWIRXFELQLPI-UHFFFAOYSA-N; NSC34875; NSC11855; MFCD00006844; SMR000059039; AK122638; NSC 11855; 4',7-Trihydroxyflavanone
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 272.25
Logarithm of the Partition Coefficient (xlogp) 2.4
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C15H12O5
IUPAC Name
5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
Canonical SMILES
C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O
InChI
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
InChIKey
FTVWIRXFELQLPI-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
932
ChEBI ID
CHEBI:50202
CAS Number
67604-48-2
DrugBank ID
DB03467
TTD ID
D02ABO
VARIDT ID
DR00833
INTEDE ID
DR2246
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Aromatase (CYP19A1) TTSZLWK CP19A_HUMAN Inhibitor [1]
Cytochrome P450 1B1 (CYP1B1) TTI84H7 CP1B1_HUMAN Inhibitor [2]
Estradiol 17 beta-dehydrogenase 1 (17-beta-HSD1) TTIWB6L DHB1_HUMAN Inhibitor [3]
Estrogen receptor beta (ESR2) TTOM3J0 ESR2_HUMAN Inhibitor [4]
Lactoylglutathione lyase (GLO1) TTV9A7R LGUL_HUMAN Inhibitor [5]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [6]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 105D7 (cyp105)
Main DME 		DECV2ME CYP28_STRAW Substrate [7], [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Estrogen receptor beta (ESR2) DTT ESR2 2.09E-01 -0.06 -0.17
P-glycoprotein 1 (ABCB1) DTP P-GP 2.55E-01 4.83E-01 5.66E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Pharmacophore modeling strategies for the development of novel nonsteroidal inhibitors of human aromatase (CYP19). Bioorg Med Chem Lett. 2010 May 15;20(10):3050-64.
2 Selective inhibition of methoxyflavonoids on human CYP1B1 activity. Bioorg Med Chem. 2010 Sep 1;18(17):6310-5.
3 Discovery of nonsteroidal 17beta-hydroxysteroid dehydrogenase 1 inhibitors by pharmacophore-based screening of virtual compound libraries. J Med Chem. 2008 Jul 24;51(14):4188-99.
4 Subtle side-chain modifications of the hop phytoestrogen 8-prenylnaringenin result in distinct agonist/antagonist activity profiles for estrogen re... J Med Chem. 2006 Dec 14;49(25):7357-65.
5 Structure-activity relationship of human GLO I inhibitory natural flavonoids and their growth inhibitory effects. Bioorg Med Chem. 2008 Apr 1;16(7):3969-75.
6 Flavonoid permeability across an in situ model of the blood-brain barrier. Free Radic Biol Med. 2004 Mar 1;36(5):592-604.
7 The metagenome of Caracolus marginella gut microbiome using culture independent approaches and shotgun sequencing. Data Brief. 2017 Nov 22;16:501-505.
8 Hydroxylation of Compactin (ML-236B) by CYP105D7 (SAV_7469) from Streptomyces avermitilis. J Microbiol Biotechnol. 2017 May 28;27(5):956-964.