IMPPAT Phytochemical information: 
Ononin
Ononin
Summary

SMILES: OC[C@H]1O[C@@H](Oc2ccc3c(c2)occ(c3=O)c2ccc(cc2)OC)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C22H22O9/c1-28-12-4-2-11(3-5-12)15-10-29-16-8-13(6-7-14(16)18(15)24)30-22-21(27)20(26)19(25)17(9-23)31-22/h2-8,10,17,19-23,25-27H,9H2,1H3/t17-,19-,20+,21-,22-/m1/s1
InChIKey: MGJLSBDCWOSMHL-MIUGBVLSSA-N
DeepSMILES: OC[C@H]O[C@@H]Occcccc6)occc6=O))cccccc6))OC)))))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=c1c(-c2ccccc2)coc2cc(OC3CCCCO3)ccc12
Scaffold Graph/Node level: OC1C(C2CCCCC2)COC2CC(OC3CCCCO3)CCC21
Scaffold Graph level: CC1C(C2CCCCC2)CCC2CC(CC3CCCCC3)CCC21
Functional groups: CO; cO[C@@H](C)OC; coc; c=O; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: Isoflavonoid O-glycosides
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
NP Classifier Class: Isoflavones
Synonymous chemical names:
ononin, formononetin 7-o-glucoside
External chemical identifiers:
CID:CID_442813; ChEMBL:CHEMBL465980; ChEBI:CHEBI:7775; ZINC:ZINC000001081322; FDASRS:Z0Z637970U; SureChEMBL:SCHEMBL240476; MolPort-001-740-570
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Ononin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 430.41
Log P RDKit 0.65
Topological polar surface area (Å2) RDKit 138.82
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.23
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.32
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
Ononin
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.459352
Ononin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -8.22
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 Yes
P-glycoprotein substrate SwissADME Yes
Ononin
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_000756ENSG00000109471IL23558ChEMBL, NPASS
TAR_EXP_000119ENSG00000101751POLI11201NPASS
TAR_EXP_000417ENSG00000111275ALDH2217BindingDB, ChEMBL, NPASS
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL
TAR_EXP_000456ENSG00000085662AKR1B1231ChEMBL, NPASS
TAR_EXP_000852ENSG00000069535MAOB4129ChEMBL
TAR_EXP_000888ENSG00000100985MMP94318ChEMBL
TAR_EXP_000966ENSG00000116044NFE2L24780NPASS
TAR_EXP_000983ENSG00000141458NPC14864ChEMBL, NPASS
TAR_EXP_001230ENSG00000100030MAPK15594ChEMBL
TAR_EXP_001231ENSG00000102882MAPK35595ChEMBL
TAR_EXP_001240ENSG00000169032MAP2K15604ChEMBL
TAR_EXP_001241ENSG00000126934MAP2K25605ChEMBL
TAR_EXP_001557ENSG00000012048BRCA1672ChEMBL, NPASS
TAR_EXP_001621ENSG00000141510TP537157ChEMBL, NPASS
TAR_EXP_001728ENSG00000176208ATAD579915ChEMBL, NPASS
TAR_EXP_001900ENSG00000123595RAB9A9367ChEMBL, NPASS