IMPPAT Phytochemical information: 
Ohchinolide A
Ohchinolide A
Summary

SMILES: CC(=O)O[C@H]1C[C@@H](OC(=O)C)[C@@]2([C@H]3[C@@]1(C)[C@H]1CC(=O)O[C@@H]4C(=C(C)[C@@H](C4)c4ccoc4)[C@]1(C)[C@@H]([C@@H]3OC2)OC(=O)c1ccccc1)C
InChI: InChI=1S/C37H42O10/c1-19-24(23-12-13-42-17-23)14-25-30(19)37(6)26(15-29(40)46-25)36(5)28(45-21(3)39)16-27(44-20(2)38)35(4)18-43-31(32(35)36)33(37)47-34(41)22-10-8-7-9-11-22/h7-13,17,24-28,31-33H,14-16,18H2,1-6H3/t24-,25+,26-,27-,28+,31-,32+,33-,35-,36+,37-/m1/s1
InChIKey: ASXOZSKFUKLCDP-SDSCJSQRSA-N
DeepSMILES: CC=O)O[C@H]C[C@@H]OC=O)C)))[C@@][C@H][C@@]6C)[C@H]CC=O)O[C@@H]C=CC)[C@@H]C5)cccoc5)))))))[C@]7C)[C@@H][C@@H]%11OC%14)))OC=O)cccccc6))))))))))))))))))C
Scaffold Graph/Node/Bond level: O=C1CC2C3CCCC4COC(C(OC(=O)c5ccccc5)C2C2=CC(c5ccoc5)CC2O1)C43
Scaffold Graph/Node level: OC1CC2C3CCCC4COC(C(OC(O)C5CCCCC5)C2C2CC(C5CCOC5)CC2O1)C43
Scaffold Graph level: CC1CC2CC(C3CCCC3)CC2C2C(C1)C1CCCC3CCC(C2CC(C)C2CCCCC2)C31
Functional groups: CC(=O)OC; COC; cC(=O)OC; CC(=C(C)C)C; coc
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: Limonoids
Synonymous chemical names:
ohchinolide a
External chemical identifiers:
CID:CID_44584371; ChEMBL:CHEMBL452907; ZINC:ZINC000049841416
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Ohchinolide A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 646.73
Log P RDKit 5.56
Topological polar surface area (Å2) RDKit 127.57
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 37
Number of heavy atoms RDKit 47
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.3
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 16
Number of sp3 hybridized carbon atoms RDKit 21
Shape complexity RDKit 0.57
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
Ohchinolide A
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 3
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.23
Ohchinolide A
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
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 -7.10
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 No
P-glycoprotein substrate SwissADME Yes