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]
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) 6
Hydrogen Bond Donor Count (hbonddonor) 8
Hydrogen Bond Acceptor Count (hbondacc) 14
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
CHEMBL451532
CAS Number
10236-47-2
UNII
N7TD9J649B
DrugBank ID
DB16859
TTD ID
D09VQM
VARIDT ID
DR00581
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

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]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Alpha-L-rhamnosidase (lrA)
Main DME 		DEBI82Z A0A1V8Q7P3_9BIF Substrate [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Catenin beta-1 (CTNNB1) OTZ932A3 CTNB1_HUMAN Gene/Protein Processing [4]
Cyclin-dependent kinase inhibitor 1 (CDKN1A) OTQWHCZE CDN1A_HUMAN Gene/Protein Processing [5]
FAS-associated death domain protein (FADD) OTV7GFHH FADD_HUMAN Gene/Protein Processing [6]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [7]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Post-Translational Modifications [7]
Osteocalcin (BGLAP) OTK1YLWQ OSTCN_HUMAN Gene/Protein Processing [8]
RAF proto-oncogene serine/threonine-protein kinase (RAF1) OT51LSFO RAF1_HUMAN Post-Translational Modifications [5]
Tumor necrosis factor receptor superfamily member 6 (FAS) OTP9XG86 TNR6_HUMAN Gene/Protein Processing [6]
Vascular cell adhesion protein 1 OTP74K37 VCAM1_HUMAN Gene/Protein Processing [9]
Molecular Interaction Atlas (MIA) 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 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.
5 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.
6 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.
7 Naringin suppresses cell metastasis and the expression of matrix metalloproteinases (MMP-2 and MMP-9) via the inhibition of ERK-P38-JNK signaling pathway in human glioblastoma. Chem Biol Interact. 2016 Jan 25;244:195-203. doi: 10.1016/j.cbi.2015.12.011. Epub 2015 Dec 22.
8 Naringin-induced bone morphogenetic protein-2 expression via PI3K, Akt, c-Fos/c-Jun and AP-1 pathway in osteoblasts. Eur J Pharmacol. 2008 Jul 7;588(2-3):333-41. doi: 10.1016/j.ejphar.2008.04.030. Epub 2008 May 19.
9 Naringin suppress chondrosarcoma migration through inhibition vascular adhesion molecule-1 expression by modulating miR-126. Int Immunopharmacol. 2014 Sep;22(1):107-14. doi: 10.1016/j.intimp.2014.06.029. Epub 2014 Jun 26.