Details of the Drug

General Information of Drug (ID: DM4DG1Y)

Drug Name

naringin

Synonyms

Naringoside; AC1NR4U8; 4',5,7-Trihydroxyflavanone-7-rutinoside; 4',5,7-Trihydroxyflavanone-7-rhamnoglucoside

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 3

Molecular Weight (mw)

580.5

Logarithm of the Partition Coefficient (xlogp)

-0.5

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C27H32O14
IUPAC Name: (2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
Canonical SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=CC(=C4C(=O)C[C@H](OC4=C3)C5=CC=C(C=C5)O)O)CO)O)O)O)O)O
InChI: InChI=1S/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1
InChIKey: DFPMSGMNTNDNHN-ZPHOTFPESA-N

Cross-matching ID

PubChem CID: 442428
ChEBI ID: CHEBI:28819
CAS Number: 10236-47-2
TTD ID: D09VQM
VARIDT ID: DR00581

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Sodium-independent organic anion transporter (SLCO1A2)	TTUGD21	SO1A2_HUMAN	Inhibitor	[2]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Alpha-L-rhamnosidase (lrA)_{Main DME}	DEBI82Z	A0A1V8Q7P3_9BIF	Substrate	[3]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Apoptosis regulator BAX (BAX)	OTAW0V4V	BAX_HUMAN	Gene/Protein Processing	[4]
Bone morphogenetic protein 4 (BMP4)	OTPZMDFH	BMP4_HUMAN	Gene/Protein Processing	[5]
Caspase-3 (CASP3)	OTIJRBE7	CASP3_HUMAN	Gene/Protein Processing	[4]
Caspase-9 (CASP9)	OTD4RFFG	CASP9_HUMAN	Gene/Protein Processing	[4]
Catenin beta-1 (CTNNB1)	OTZ932A3	CTNB1_HUMAN	Gene/Protein Processing	[5]
Cellular tumor antigen p53 (TP53)	OTIE1VH3	P53_HUMAN	Gene/Protein Processing	[4]
Cyclin-dependent kinase inhibitor 1 (CDKN1A)	OTQWHCZE	CDN1A_HUMAN	Gene/Protein Processing	[6]
Cytochrome P450 1A1 (CYP1A1)	OTE4EFH8	CP1A1_HUMAN	Gene/Protein Processing	[7]
Cytochrome P450 1A2 (CYP1A2)	OTLLBX48	CP1A2_HUMAN	Gene/Protein Processing	[7]
Cytochrome P450 3A4 (CYP3A4)	OTQGYY83	CP3A4_HUMAN	Gene/Protein Processing	[8]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

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: 4738).
2	Naringin is a major and selective clinical inhibitor of organic anion-transporting polypeptide 1A2 (OATP1A2) in grapefruit juice. Clin Pharmacol Ther. 2007 Apr;81(4):495-502.
3	Metabolism of rutin and poncirin by human intestinal microbiota and cloning of their metabolizing alpha-L-rhamnosidase from Bifidobacterium dentium. J Microbiol Biotechnol. 2015 Jan;25(1):18-25.
4	Naringin induces death receptor and mitochondria-mediated apoptosis in human cervical cancer (SiHa) cells. Food Chem Toxicol. 2013 Jan;51:97-105. doi: 10.1016/j.fct.2012.07.033. Epub 2012 Jul 27.
5	Effects of naringin on the proliferation and osteogenic differentiation of human amniotic fluid-derived stem cells. J Tissue Eng Regen Med. 2017 Jan;11(1):276-284. doi: 10.1002/term.1911. Epub 2014 Jun 11.
6	Requirement for Ras/Raf/ERK pathway in naringin-induced G1-cell-cycle arrest via p21WAF1 expression. Carcinogenesis. 2008 Sep;29(9):1701-9. doi: 10.1093/carcin/bgn055. Epub 2008 Feb 22.
7	Structure-function relationships of inhibition of human cytochromes P450 1A1, 1A2, 1B1, 2C9, and 3A4 by 33 flavonoid derivatives. Chem Res Toxicol. 2010 Dec 20;23(12):1921-35.
8	Effects of naringin on the pharmacokinetics of verapamil and one of its metabolites, norverapamil, in rabbits. Biopharm Drug Dispos. 2005 Oct;26(7):295-300.