IMPPAT Phytochemical information: 
Virgatic acid
Virgatic acid
Summary

SMILES: O=C1C[C@H](O)C([C@H]2[C@@]1(C)[C@H]1CC=C3[C@@]([C@@]1(CC2)C)(C)CC[C@@]1([C@H]3CC(C)(C)CC1)C(=O)O)(C)C
InChI: InChI=1S/C30H46O4/c1-25(2)12-14-30(24(33)34)15-13-27(5)18(19(30)17-25)8-9-21-28(27,6)11-10-20-26(3,4)22(31)16-23(32)29(20,21)7/h8,19-22,31H,9-17H2,1-7H3,(H,33,34)/t19-,20-,21-,22-,27+,28+,29-,30-/m0/s1
InChIKey: IZWBODJDDBCDFA-DXEZAUPJSA-N
DeepSMILES: O=CC[C@H]O)C[C@H][C@@]6C)[C@H]CC=C[C@@][C@@]6CC%10))C))C)CC[C@@][C@H]6CCC)C)CC6)))))C=O)O))))))))))))C)C
Scaffold Graph/Node/Bond level: O=C1CCCC2CCC3C4CCC5CCCCC5C4=CCC3C12
Scaffold Graph/Node level: OC1CCCC2CCC3C4CCC5CCCCC5C4CCC3C12
Scaffold Graph level: CC1CCCC2CCC3C4CCC5CCCCC5C4CCC3C12
Functional groups: CC(=O)C; CO; CC=C(C)C; CC(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Triterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Oleanane triterpenoids
Synonymous chemical names:
vergatic acid, momordic acid, Vergatic acid
External chemical identifiers:
CID:CID_14489125; ChEBI:CHEBI:67945; ZINC:ZINC000033832838; FDASRS:7K3293BNX3
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Virgatic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 470.69
Log P RDKit 6.41
Topological polar surface area (Å2) RDKit 74.6
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 34
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.27
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 26
Shape complexity RDKit 0.87
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Virgatic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.434123
Virgatic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
Solubility class [ESOL] SwissADME Poorly 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 -4.78
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 Yes