IMPPAT Phytochemical information: 
Naringin
Naringin
Summary

SMILES: OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2)O[C@@H](CC3=O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)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
DeepSMILES: OC[C@H]O[C@@H]OcccO)ccc6)O[C@@H]CC6=O)))cccccc6))O)))))))))))))[C@@H][C@H][C@@H]6O))O))O[C@@H]O[C@@H]C)[C@@H][C@H][C@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1CC(c2ccccc2)Oc2cc(OC3OCCCC3OC3CCCCO3)ccc21
Scaffold Graph/Node level: OC1CC(C2CCCCC2)OC2CC(OC3OCCCC3OC3CCCCO3)CCC12
Scaffold Graph level: CC1CC(C2CCCCC2)CC2CC(CC3CCCCC3CC3CCCCC3)CCC12
Functional groups: CO; CO[C@@H](C)OC; cO[C@@H](C)OC; cO; cOC; cC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Flavonoid glycosides
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavanones
Synonymous chemical names:
Naringin, naringin
External chemical identifiers:
CID:CID_442428; ChEMBL:CHEMBL451532; ChEBI:CHEBI:28819; ZINC:ZINC000008143604; FDASRS:N7TD9J649B; SureChEMBL:SCHEMBL23432; MolPort-001-742-592
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Naringin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 580.54
Log P RDKit -1.17
Topological polar surface area (Å2) RDKit 225.06
Number of hydrogen bond acceptors RDKit 14
Number of hydrogen bond donors RDKit 8
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 41
Number of heteroatoms RDKit 14
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.41
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.52
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Naringin
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 4
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.201696
Naringin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -10.15
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes
Naringin
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000475ENSG00000120948TARDBP23435NPASS
TAR_EXP_000414ENSG00000170323FABP42167ChEMBL
TAR_EXP_000392ENSG00000157554ERG2078NPASS
TAR_EXP_000285ENSG00000137869CYP19A11588BindingDB, ChEMBL, NPASS
TAR_EXP_000132ENSG00000137491SLCO2B111309ChEMBL, NPASS
TAR_EXP_001659ENSG00000277132UGT2B157366ChEMBL, NPASS
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_001663ENSG00000162607USP17398NPASS
TAR_EXP_001651ENSG00000177889UBE2N7334BindingDB, ChEMBL, NPASS
TAR_EXP_001536ENSG00000084453SLCO1A26579ChEMBL
TAR_EXP_001306ENSG00000196396PTPN15770BindingDB, ChEMBL, NPASS
TAR_EXP_001168ENSG00000241635UGT1A154658ChEMBL, NPASS
TAR_EXP_000097ENSG00000108468CBX110951NPASS
TAR_EXP_001167ENSG00000244474UGT1A454657ChEMBL, NPASS
TAR_EXP_001148ENSG00000172115CYCS54205ChEMBL, NPASS
TAR_EXP_000801ENSG00000157542KCNJ63763ChEMBL, NPASS
TAR_EXP_001857ENSG00000104321TRPA18989ChEMBL, NPASS
TAR_EXP_001106ENSG00000085563ABCB15243ChEMBL
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_000095ENSG00000224143EHMT210919ChEMBL, NPASS
TAR_EXP_000800ENSG00000120457KCNJ53762BindingDB, ChEMBL, NPASS
TAR_EXP_000799ENSG00000162989KCNJ33760BindingDB, ChEMBL
TAR_EXP_000747ENSG00000138413IDH13417NPASS
TAR_EXP_000660ENSG00000082701GSK3B2932BindingDB, ChEMBL, NPASS
TAR_EXP_000086ENSG00000173083HPSE10855BindingDB, ChEMBL, NPASS