IMPPAT Phytochemical information: 
Garcinolic acid
Garcinolic acid
Summary

SMILES: CC(=CCc1c2OC34C(=CCCC3C(O[C@@]4(C/C=C(/C(=O)O)\C)C(=O)O)(C)C)C(=O)c2c(c2c1OC(C)(CCC=C(C)C)C=C2)O)C
InChI: InChI=1S/C38H46O9/c1-21(2)11-10-18-36(8)19-17-24-29(39)28-30(40)26-12-9-13-27-35(6,7)47-37(34(43)44,20-16-23(5)33(41)42)38(26,27)46-32(28)25(31(24)45-36)15-14-22(3)4/h11-12,14,16-17,19,27,39H,9-10,13,15,18,20H2,1-8H3,(H,41,42)(H,43,44)/b23-16+/t27?,36?,37-,38?/m0/s1
InChIKey: VDSCKSOYNLTQSY-VGJPRPLGSA-N
DeepSMILES: CC=CCccOCC=CCCC6CO[C@@]9C/C=C/C=O)O))\C))))C=O)O))))C)C))))))C=O)c6ccc%10OCC)CCC=CC)C)))))C=C6))))))O)))))))))))C
Scaffold Graph/Node/Bond level: O=C1C2=CCCC3COCC23Oc2cc3c(cc21)C=CCO3
Scaffold Graph/Node level: OC1C2CC3CCCOC3CC2OC23COCC2CCCC13
Scaffold Graph level: CC1C2CC3CCCCC3CC2CC23CCCC2CCCC13
Functional groups: CC=C(C)C; cOC; cC(=O)C(=CC)C; COC; C/C=C(\C)C(=O)O; CC(=O)O; cC=CC; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzopyrans
ClassyFire Subclass: 1-benzopyrans
NP Classifier Biosynthetic pathway: Terpenoids
Synonymous chemical names:
garcinolic acid, garcinolic-acids
External chemical identifiers:
CID:CID_6857794; ChEMBL:CHEMBL1456870; SureChEMBL:SCHEMBL13287227
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Garcinolic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 646.78
Log P RDKit 7.52
Topological polar surface area (Å2) RDKit 139.59
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 38
Number of heavy atoms RDKit 47
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.11
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 19
Number of sp3 hybridized carbon atoms RDKit 19
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 9
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
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 5
Garcinolic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 4
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 0.183615
Garcinolic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -4.82
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
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