IMPPAT Phytochemical information: 
Neogambogic acid
Neogambogic acid
Summary

SMILES: CC(=CCc1c2OC34C(=CC5CC3C(OC4(C/C=C(/C(=O)O)\C)C5=O)(C)C)C(=O)c2c(c2c1OC(C)(CCC=C(C)C)CC2O)O)C
InChI: InChI=1S/C38H46O9/c1-19(2)10-9-14-36(8)18-25(39)27-30(41)28-29(40)24-16-22-17-26-35(6,7)47-37(33(22)42,15-13-21(5)34(43)44)38(24,26)46-32(28)23(31(27)45-36)12-11-20(3)4/h10-11,13,16,22,25-26,39,41H,9,12,14-15,17-18H2,1-8H3,(H,43,44)/b21-13+
InChIKey: BLDWFKHVHHINGR-FYJGNVAPSA-N
DeepSMILES: CC=CCccOCC=CCCC6COC9C/C=C/C=O)O))\C))))C7=O))))C)C))))))C=O)c6ccc%10OCC)CCC=CC)C)))))CC6O)))))))O)))))))))))C
Scaffold Graph/Node/Bond level: O=C1C2=CC3CC4COC(C3=O)C24Oc2cc3c(cc21)CCCO3
Scaffold Graph/Node level: OC1C2CC3CCCOC3CC2OC23C4COC2C(O)C(C4)CC13
Scaffold Graph level: CC1C2CC3CCC1C31CC3CC4CCCCC4CC3C(C)C1C2
Functional groups: CC=C(C)C; cOC; cC(=O)C(=CC)C; COC; C/C=C(\C)C(=O)O; CC(=O)C; CO; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzopyrans
ClassyFire Subclass: 1-benzopyrans
NP Classifier Biosynthetic pathway: Polyketides|Shikimates and Phenylpropanoids|Terpenoids
NP Classifier Superclass: Xanthones
NP Classifier Class: Plant xanthones
Synonymous chemical names:
neogambogic-acid
External chemical identifiers:
CID:CID_6438568; MolPort-027-720-685
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Neogambogic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 646.78
Log P RDKit 6.65
Topological polar surface area (Å2) RDKit 139.59
Number of hydrogen bond acceptors RDKit 8
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 6
Stereochemical complexity RDKit 0.16
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 17
Number of sp3 hybridized carbon atoms RDKit 21
Shape complexity RDKit 0.55
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
Neogambogic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 4
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.21
Neogambogic 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 -5.79
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