IMPPAT Phytochemical information: 
Apo-12'-violaxanthal

Apo-12'-violaxanthal
Summary

SMILES: O=C/C(=C\C=C\C=C(\C=C\C=C(/C=C/C12OC2(C)CC(CC1(C)C)O)\C)/C)/C
InChI: InChI=1S/C25H34O3/c1-19(10-7-8-11-21(3)18-26)12-9-13-20(2)14-15-25-23(4,5)16-22(27)17-24(25,6)28-25/h7-15,18,22,27H,16-17H2,1-6H3/b8-7+,12-9+,15-14+,19-10+,20-13-,21-11-
InChIKey: CAXVJDRXJFKYQP-RXCALXPUSA-N
DeepSMILES: O=C/C=C\C=C\C=C\C=C\C=C/C=C/COC3C)CCCC7C)C)))O))))))))\C)))))/C))))))/C
Scaffold Graph/Node/Bond level: C1CCC2OC2C1
Scaffold Graph/Node level: C1CCC2OC2C1
Scaffold Graph level: C1CCC2CC2C1
Functional groups: C/C(C=O)=C/C=C/C=C(C)/C=C/C=C(C)\C=C\C1(C)OC1(C)C; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Diterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Apocarotenoids
NP Classifier Class: Apocarotenoids (β-)
Synonymous chemical names:
12'-apoviolaxanthal, apo-12'-violaxanthal
External chemical identifiers:
CID:CID_131751642; ChEBI:CHEBI:171885
Chemical structure download


Apo-12'-violaxanthal
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 382.54
Log P RDKit 5.4
Topological polar surface area (Å2) RDKit 49.83
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 25
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.12
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.48
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
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 2


Apo-12'-violaxanthal
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 0
Ghose rule RDKit Passed
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 0.28


Apo-12'-violaxanthal
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -11.90
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 No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No