IMPPAT Phytochemical information: 
Vaginidin

Vaginidin
Summary

SMILES: CC(CC(=O)O[C@@H]1c2c(O[C@@H]1C(O)(C)C)ccc1c2oc(=O)cc1)C
InChI: InChI=1S/C19H22O6/c1-10(2)9-14(21)25-17-15-12(23-18(17)19(3,4)22)7-5-11-6-8-13(20)24-16(11)15/h5-8,10,17-18,22H,9H2,1-4H3/t17-,18+/m1/s1
InChIKey: VKTNFVWVAQYYBV-MSOLQXFVSA-N
DeepSMILES: CCCC=O)O[C@@H]ccO[C@@H]5CO)C)C))))cccc6oc=O)cc6))))))))))))))C
Scaffold Graph/Node/Bond level: O=c1ccc2ccc3c(c2o1)CCO3
Scaffold Graph/Node level: OC1CCC2CCC3OCCC3C2O1
Scaffold Graph level: CC1CCC2CCC3CCCC3C2C1
Functional groups: CC(=O)OC; cOC; CO; coc; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Coumarins and derivatives
ClassyFire Subclass: Furanocoumarins
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Furocoumarins|Simple coumarins
Synonymous chemical names:
vaginidin
External chemical identifiers:
CID:CID_12299857; ZINC:ZINC000014826979
Chemical structure download


Vaginidin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 346.38
Log P RDKit 2.96
Topological polar surface area (Å2) RDKit 85.97
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.11
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.47
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 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Vaginidin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.68


Vaginidin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.54
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No