IMPPAT Phytochemical information: 
Semimoronic acid
Semimoronic acid
Summary

SMILES: OC(=O)[C@]12CC[C@@]3([C@@H](C2=CC(CC1)(C)C)CC[C@H]1[C@@]3(C)CC[C@@H]2[C@@]31CC[C@@](C2(C)C)(OC3)O)C
InChI: InChI=1S/C30H46O4/c1-24(2)11-13-28(23(31)32)14-12-26(5)19(20(28)17-24)7-8-22-27(26,6)10-9-21-25(3,4)30(33)16-15-29(21,22)18-34-30/h17,19,21-22,33H,7-16,18H2,1-6H3,(H,31,32)/t19-,21+,22+,26-,27-,28+,29-,30+/m1/s1
InChIKey: ILAJTNIQGKGJFB-XQVSGEKFSA-N
DeepSMILES: OC=O)[C@@]CC[C@@][C@@H]C6=CCCC%10))C)C))))CC[C@H][C@@]6C)CC[C@@H][C@]6CC[C@@]C6C)C))OC6))O)))))))))))))C
Scaffold Graph/Node/Bond level: C1=C2C(CCC1)CCC1C2CCC2C1CCC1CC3CCC12CO3
Scaffold Graph/Node level: C1CCC2C(C1)CCC1C2CCC2C1CCC1CC3CCC12CO3
Scaffold Graph level: C1CCC2C(C1)CCC1C2CCC2C1CCC1CC3CCC12CC3
Functional groups: CC(=O)O; CO[C@@](O)(C)C; CC=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Naphthopyrans
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Oleanane triterpenoids
Synonymous chemical names:
semimoronic acid, Semimoronic acid
External chemical identifiers:
CID:CID_21669113
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Semimoronic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 470.69
Log P RDKit 6.57
Topological polar surface area (Å2) RDKit 66.76
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 3
Number of sp3 hybridized carbon atoms RDKit 27
Shape complexity RDKit 0.9
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 7
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 6
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
Semimoronic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 3
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 0.43
Semimoronic 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 -4.39
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 Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No