IMPPAT Phytochemical information: 
(1R,2S,6R,10S,11R,13S,15R)-1,6,13-trihydroxy-8,12-bis(hydroxymethyl)-4,12,15-trimethyltetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dien-5-one
(1R,2S,6R,10S,11R,13S,15R)-1,6,13-trihydroxy-8,12-bis(hydroxymethyl)-4,12,15-trimethyltetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dien-5-one
Summary

SMILES: OCC1=C[C@H]2[C@@H]3C([C@]3(O)C[C@H]([C@@]2([C@H]2[C@@](C1)(O)C(=O)C(=C2)C)O)C)(C)CO
InChI: InChI=1S/C20H28O6/c1-10-4-14-18(24,16(10)23)7-12(8-21)5-13-15-17(3,9-22)19(15,25)6-11(2)20(13,14)26/h4-5,11,13-15,21-22,24-26H,6-9H2,1-3H3/t11-,13+,14-,15-,17?,18-,19+,20-/m1/s1
InChIKey: XDOXADBJFQBBMY-JZHRCRMDSA-N
DeepSMILES: OCC=C[C@H][C@@H]C[C@]3O)C[C@H][C@@]7[C@H][C@@]C%12)O)C=O)C=C5)C)))))O))C))))C)CO
Scaffold Graph/Node/Bond level: O=C1C=CC2C1CC=CC1C3CC3CCC21
Scaffold Graph/Node level: OC1CCC2C1CCCC1C3CC3CCC21
Scaffold Graph level: CC1CCC2C1CCCC1C3CC3CCC21
Functional groups: CO; CC(=CC)C; CC1=CCCC1=O
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: Diterpenoids
NP Classifier Class: Tetracyclic diterpenoids|Tigliane diterpenoids
Synonymous chemical names:
12-deoxy-16-oh-phorbol
External chemical identifiers:
CID:CID_101045971
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1R,2S,6R,10S,11R,13S,15R)-1,6,13-trihydroxy-8,12-bis(hydroxymethyl)-4,12,15-trimethyltetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dien-5-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 364.44
Log P RDKit -0.07
Topological polar surface area (Å2) RDKit 118.22
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 5
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 8
Stereochemical complexity RDKit 0.4
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.75
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 0
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 0
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
(1R,2S,6R,10S,11R,13S,15R)-1,6,13-trihydroxy-8,12-bis(hydroxymethyl)-4,12,15-trimethyltetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dien-5-one
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.437971
(1R,2S,6R,10S,11R,13S,15R)-1,6,13-trihydroxy-8,12-bis(hydroxymethyl)-4,12,15-trimethyltetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dien-5-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 -8.91
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