IMPPAT Phytochemical information: 
Spinosic acid B, dimethyl ester, acetate

Spinosic acid B, dimethyl ester, acetate
Summary

SMILES: COC(=O)C12CCC3(C(C1=CCC1C2(C)CCC2C1(C)CCC(C2(C)C)OC(=O)C)C(C)C(CC3)C)C(=O)OC
InChI: InChI=1S/C34H52O6/c1-20-12-17-33(28(36)38-8)18-19-34(29(37)39-9)23(27(33)21(20)2)10-11-25-31(6)15-14-26(40-22(3)35)30(4,5)24(31)13-16-32(25,34)7/h10,20-21,24-27H,11-19H2,1-9H3
InChIKey: KYJQFQFOEOMJTE-UHFFFAOYSA-N
DeepSMILES: COC=O)CCCCCC6=CCCC%10C)CCCC6C)CCCC6C)C))OC=O)C)))))))))))))))CC)CCC6))C))))C=O)OC
Scaffold Graph/Node/Bond level: C1=C2C3CCCCC3CCC2C2CCC3CCCCC3C2C1
Scaffold Graph/Node level: C1CCC2C(C1)CCC1C2CCC2C3CCCCC3CCC21
Scaffold Graph level: C1CCC2C(C1)CCC1C2CCC2C3CCCCC3CCC21
Functional groups: COC(C)=O; CC=C(C)C
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: Ursane and Taraxastane triterpenoids
Synonymous chemical names:
spinosic acid b
External chemical identifiers:
CID:CID_605534
Chemical structure download


Spinosic acid B, dimethyl ester, acetate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 556.78
Log P RDKit 6.9
Topological polar surface area (Å2) RDKit 78.9
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 34
Number of heavy atoms RDKit 40
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.29
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 29
Shape complexity RDKit 0.85
Number of rotatable bonds RDKit 6
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


Spinosic acid B, dimethyl ester, acetate
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 0.213696


Spinosic acid B, dimethyl ester, acetate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
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 -4.65
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