Secondary metabolite: 29-Hydroxydehydropachymic acid



29-Hydroxydehydropachymic acid
Summary
Molecular formula: C33H50O6
SMILES: OC[C@@]1(C)[C@H](CC[C@]2([C@H]1CC=C1C2=CC[C@]2([C@@]1(C)C[C@H]([C@@H]2[C@H](C(=O)O)CCC(=C)C(C)C)O)C)C)OC(=O)C
InChI: InChI=1S/C33H50O6/c1-19(2)20(3)9-10-22(29(37)38)28-25(36)17-33(8)24-11-12-26-30(5,23(24)13-16-32(28,33)7)15-14-27(39-21(4)35)31(26,6)18-34/h11,13,19,22,25-28,34,36H,3,9-10,12,14-18H2,1-2,4-8H3,(H,37,38)/t22-,25-,26-,27+,28+,30-,31-,32-,33+/m1/s1
InChIKey: USCUFHFTPQCOLH-YXMYOOBPSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Prenol lipids
Sub class: Triterpenoids
Synonymous chemical names:
29-hydroxydehydropachymic acid
Chemical structure download



29-Hydroxydehydropachymic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 542.76
Log P RDKit 6.08
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 33
Number of heavy atoms RDKit 39
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.27
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 25
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.76
Shape complexity RDKit 0.76
Number of rotatable bonds SwissADME 9
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



29-Hydroxydehydropachymic 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’s 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Number of Leadlikeness violations SwissADME 3
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.25



29-Hydroxydehydropachymic acid
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -5.56
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 Yes
P-glycoprotein substrate SwissADME Yes




Designed by R.P. Vivek-Ananth, M Karthikeyan and Ajaya Kumar Sahoo