IMPPAT Phytochemical information: 
(1S,3R,8R,11S,12S,14S,15R,16R)-14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.01,3.03,8.012,16]octadecan-6-one
(1S,3R,8R,11S,12S,14S,15R,16R)-14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.01,3.03,8.012,16]octadecan-6-one
Summary

SMILES: O[C@H]1C[C@@]2([C@]([C@H]1C1(C)CCC(O1)C(O)(C)C)(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)CCC(=O)C2(C)C)C
InChI: InChI=1S/C30H48O4/c1-24(2)19-8-9-20-27(6)16-18(31)23(28(7)12-11-22(34-28)25(3,4)33)26(27,5)14-15-30(20)17-29(19,30)13-10-21(24)32/h18-20,22-23,31,33H,8-17H2,1-7H3/t18-,19-,20-,22?,23-,26+,27-,28?,29+,30-/m0/s1
InChIKey: RBRKRLQNZMJOLD-BWHBNEHYSA-N
DeepSMILES: O[C@H]C[C@@][C@][C@H]5CC)CCCO5)CO)C)C)))))))C)CC[C@][C@H]6CC[C@@H][C@]6C7)CCC=O)C6C)C))))))))))))))C
Scaffold Graph/Node/Bond level: O=C1CCC23CC24CCC2C(C5CCCO5)CCC2C4CCC3C1
Scaffold Graph/Node level: OC1CCC23CC24CCC2C(C5CCCO5)CCC2C4CCC3C1
Scaffold Graph level: CC1CCC23CC24CCC2C(C5CCCC5)CCC2C4CCC3C1
Functional groups: CO; COC; CC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene glycosides
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Cycloartane triterpenoids
Synonymous chemical names:
argentatin a
External chemical identifiers:
CID:CID_10434965
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1S,3R,8R,11S,12S,14S,15R,16R)-14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.01,3.03,8.012,16]octadecan-6-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 472.71
Log P RDKit 5.67
Topological polar surface area (Å2) RDKit 66.76
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 34
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.33
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 1
Number of sp3 hybridized carbon atoms RDKit 29
Shape complexity RDKit 0.97
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 5
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 6
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
(1S,3R,8R,11S,12S,14S,15R,16R)-14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.01,3.03,8.012,16]octadecan-6-one
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 3
Ghose rule RDKit Failed
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 0.54
(1S,3R,8R,11S,12S,14S,15R,16R)-14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.01,3.03,8.012,16]octadecan-6-one
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.34
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
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