Secondary metabolite: (24E)-3,4-seco-cucurbita-4,24-diene-3,26,29-trioic acid



(24E)-3,4-seco-cucurbita-4,24-diene-3,26,29-trioic acid
Summary
Molecular formula: C30H46O6
SMILES: OC(=O)CC[C@@H]1/C(=C(C(=O)O)/C)/CC[C@@H]2[C@@]1(C)CC[C@]1([C@@]2(C)CC[C@@H]1[C@H](CC/C=C(/C(=O)O)C)C)C
InChI: InChI=1S/C30H46O6/c1-18(8-7-9-19(2)26(33)34)22-14-15-30(6)24-12-10-21(20(3)27(35)36)23(11-13-25(31)32)28(24,4)16-17-29(22,30)5/h9,18,22-24H,7-8,10-17H2,1-6H3,(H,31,32)(H,33,34)(H,35,36)/b19-9+,21-20-/t18-,22+,23+,24+,28-,29+,30-/m0/s1
InChIKey: MLKGNOBMWJPGDM-OYWJSAOISA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Prenol lipids
Sub class: Triterpenoids
Synonymous chemical names:
(24e)-3,4-seco-cucurbita-4,24-diene-3,26,29-trioic acid, (24e)-3,4-secocucurbita-4,24-diene-3,26,29-trioic acid
Chemical structure download



(24E)-3,4-seco-cucurbita-4,24-diene-3,26,29-trioic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 502.69
Log P RDKit 6.95
Topological polar surface area (Å2) RDKit 111.9
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 36
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.23
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 23
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.77
Shape complexity RDKit 0.77
Number of rotatable bonds SwissADME 9
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



(24E)-3,4-seco-cucurbita-4,24-diene-3,26,29-trioic 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 0.29



(24E)-3,4-seco-cucurbita-4,24-diene-3,26,29-trioic 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 -4.46
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 Yes
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