IMPPAT Phytochemical information: 
Caryophylla-4(14),8(15)-dien-5alpha-ol
Caryophylla-4(14),8(15)-dien-5alpha-ol
Summary

SMILES: C=C1CC[C@@H](O)C(=C)C2C(CC1)C(C2)(C)C
InChI: InChI=1S/C15H24O/c1-10-5-7-13-12(9-15(13,3)4)11(2)14(16)8-6-10/h12-14,16H,1-2,5-9H2,3-4H3/t12?,13?,14-/m1/s1
InChIKey: SYKFIZVLWNPGLS-JXQTWKCFSA-N
DeepSMILES: C=CCC[C@@H]O)C=C)CCCC9))CC4)C)C
Scaffold Graph/Node/Bond level: C=C1CCCC(=C)C2CCC2CC1
Scaffold Graph/Node level: CC1CCCC(C)C2CCC2CC1
Scaffold Graph level: CC1CCCC(C)C2CCC2CC1
Functional groups: C=C(C)C; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Sesquiterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Caryophyllane sesquiterpenoids
Synonymous chemical names:
caryophylla-4(14),8(15)-dien-5alpha-ol, (3R)-10,10-dimethyl-2,6-dimethylidenebicyclo[7.2.0]undecan-3-ol, caryophylla-4(14),8(15)dien-5-α-ol, caryophylla-4(14),8(15) dien-5α-ol
External chemical identifiers:
CID:CID_101638579
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Caryophylla-4(14),8(15)-dien-5alpha-ol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 220.36
Log P RDKit 3.7
Topological polar surface area (Å2) RDKit 20.23
Number of hydrogen bond acceptors RDKit 1
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 16
Number of heteroatoms RDKit 1
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.2
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.73
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 0
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 2
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
Caryophylla-4(14),8(15)-dien-5alpha-ol
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.617179
Caryophylla-4(14),8(15)-dien-5alpha-ol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.29
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No