IMPPAT Phytochemical information: 
Dammarenolic acid

Dammarenolic acid
Summary

SMILES: OC(=O)CC[C@@]1(C)[C@@H](CC[C@@]2([C@@H]1CC[C@H]1[C@@]2(C)CC[C@@H]1[C@](CCC=C(C)C)(O)C)C)C(=C)C
InChI: InChI=1S/C30H50O3/c1-20(2)10-9-16-30(8,33)24-14-18-28(6)23(24)11-12-25-27(5,17-15-26(31)32)22(21(3)4)13-19-29(25,28)7/h10,22-25,33H,3,9,11-19H2,1-2,4-8H3,(H,31,32)/t22-,23+,24-,25+,27-,28+,29+,30-/m0/s1
InChIKey: SITSHJMXTJRDSK-HPNZNPLMSA-N
DeepSMILES: OC=O)CC[C@@]C)[C@@H]CC[C@@][C@@H]6CC[C@H][C@@]6C)CC[C@@H]5[C@]CCC=CC)C)))))O)C))))))))))C))))C=C)C
Scaffold Graph/Node/Bond level: C1CCC2C(C1)CCC1CCCC12
Scaffold Graph/Node level: C1CCC2C(C1)CCC1CCCC12
Scaffold Graph level: C1CCC2C(C1)CCC1CCCC12
Functional groups: CC(=O)O; CC=C(C)C; CO; C=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Sesterterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Dammarane and Protostane triterpenoids
Synonymous chemical names:
dammarenolic acid, Dammarenolic acid, dammarenolic-acid
External chemical identifiers:
CID:CID_22215841; ChEMBL:CHEMBL517674; ZINC:ZINC000040410807
Chemical structure download


Dammarenolic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 458.73
Log P RDKit 7.79
Topological polar surface area (Å2) RDKit 57.53
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 33
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.27
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 25
Shape complexity RDKit 0.83
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Dammarenolic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 3
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 0.364909


Dammarenolic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
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 -2.99
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 No