IMPPAT Phytochemical information: 
(1R,2R,6R,7R,8S,11S,12R)-2,6,8,12-tetrahydroxy-3,7,11-trimethyl-4-propan-2-yl-13-oxatetracyclo[5.5.3.01,8.02,6]pentadec-3-en-14-one
(1R,2R,6R,7R,8S,11S,12R)-2,6,8,12-tetrahydroxy-3,7,11-trimethyl-4-propan-2-yl-13-oxatetracyclo[5.5.3.01,8.02,6]pentadec-3-en-14-one
Summary

SMILES: O=C1O[C@@]23[C@H](O)[C@@H](C)CC[C@@]3([C@@](C1)(C)[C@]1([C@]2(O)C(=C(C1)C(C)C)C)O)O
InChI: InChI=1S/C20H30O6/c1-10(2)13-8-18(24)16(5)9-14(21)26-20(19(18,25)12(13)4)15(22)11(3)6-7-17(16,20)23/h10-11,15,22-25H,6-9H2,1-5H3/t11-,15+,16-,17-,18+,19+,20+/m0/s1
InChIKey: JFDHTDLZWVKRQT-KGRJDOQESA-N
DeepSMILES: O=CO[C@][C@H]O)[C@@H]C)CC[C@@]6[C@@]C%10)C)[C@][C@]9O)C=CC5)CC)C)))C)))O)))O
Scaffold Graph/Node/Bond level: O=C1CC2C3CC=CC3C3(CCCCC23)O1
Scaffold Graph/Node level: OC1CC2C3CCCC3C3(CCCCC23)O1
Scaffold Graph level: CC1CC2C3CCCC3C3(CCCCC23)C1
Functional groups: CC(=O)OC; CO; CC(C)=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene lactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
Synonymous chemical names:
anhydrocinnzeylanol
External chemical identifiers:
CID:CID_11783510; ZINC:ZINC000036434459
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1R,2R,6R,7R,8S,11S,12R)-2,6,8,12-tetrahydroxy-3,7,11-trimethyl-4-propan-2-yl-13-oxatetracyclo[5.5.3.01,8.02,6]pentadec-3-en-14-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 366.45
Log P RDKit 1.05
Topological polar surface area (Å2) RDKit 107.22
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.35
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 17
Shape complexity RDKit 0.85
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
(1R,2R,6R,7R,8S,11S,12R)-2,6,8,12-tetrahydroxy-3,7,11-trimethyl-4-propan-2-yl-13-oxatetracyclo[5.5.3.01,8.02,6]pentadec-3-en-14-one
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
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 Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.41
(1R,2R,6R,7R,8S,11S,12R)-2,6,8,12-tetrahydroxy-3,7,11-trimethyl-4-propan-2-yl-13-oxatetracyclo[5.5.3.01,8.02,6]pentadec-3-en-14-one
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -8.78
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 Yes