IMPPAT Phytochemical information: 
(11aR)-10-hydroxy-9-[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-5a,5b,8,8,11a,13a-hexamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,9,10,11,11b,12,13,13b-tetradecahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid
(11aR)-10-hydroxy-9-[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-5a,5b,8,8,11a,13a-hexamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,9,10,11,11b,12,13,13b-tetradecahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid
Summary

SMILES: O=C(OC1C(O)C[C@]2(C(C1(C)C)CCC1(C2CCC2(C1(C)CCC1(C2C(CC1)C(=C)C)C(=O)O)C)C)C)/C=C\c1ccc(cc1)O
InChI: InChI=1S/C40H56O6/c1-24(2)27-15-20-40(34(44)45)22-21-39(8)37(6)18-16-29-35(3,4)33(46-31(43)14-11-25-9-12-26(41)13-10-25)28(42)23-36(29,5)30(37)17-19-38(39,7)32(27)40/h9-14,27-30,32-33,41-42H,1,15-23H2,2-8H3,(H,44,45)/b14-11-/t27?,28?,29?,30?,32?,33?,36-,37?,38?,39?,40?/m0/s1
InChIKey: RNFUOEDBPUVMOC-FDLIQPMOSA-N
DeepSMILES: O=COCCO)C[C@]CC6C)C))CCCC6CCCC6C)CCCC6CCC5))C=C)C))))C=O)O))))))C)))))C)))))C))))))/C=C\cccccc6))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OC1CCC2C(CCC3C2CCC2C4CCCC4CCC23)C1
Scaffold Graph/Node level: OC(CCC1CCCCC1)OC1CCC2C(CCC3C2CCC2C4CCCC4CCC23)C1
Scaffold Graph level: CC(CCC1CCCCC1)CC1CCC2C(CCC3C2CCC2C4CCCC4CCC23)C1
Functional groups: c/C=C\C(=O)OC; CC(=O)O; CO; cO; C=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Triterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Lupane triterpenoids
Synonymous chemical names:
3-o-cis-p-coumaroylalphitolic acid
External chemical identifiers:
CID:CID_5316118
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(11aR)-10-hydroxy-9-[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-5a,5b,8,8,11a,13a-hexamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,9,10,11,11b,12,13,13b-tetradecahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 632.88
Log P RDKit 8.42
Topological polar surface area (Å2) RDKit 104.06
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 40
Number of heavy atoms RDKit 46
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.28
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 28
Shape complexity RDKit 0.7
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 5
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
(11aR)-10-hydroxy-9-[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-5a,5b,8,8,11a,13a-hexamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,9,10,11,11b,12,13,13b-tetradecahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 4
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.171056
(11aR)-10-hydroxy-9-[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-5a,5b,8,8,11a,13a-hexamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,9,10,11,11b,12,13,13b-tetradecahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -3.11
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes