MeFSAT | MeFSAT: Medicinal Fungi Secondary metabolites And Therapeutics

Secondary metabolite: 3a-(3-Hydroxy-5-methoxy-3-methyl-1,5-dioxopentyloxy)-24-methylene-5 a -lanost-8-en-21-oic acid

Summary

Molecular formula: C38H60O7
SMILES: COC(=O)CC(CC(=O)O[C@@H]1CC[C@]2([C@H](C1(C)C)CCC1=C2CC[C@]2([C@@]1(C)CC[C@@H]2[C@H](C(=O)O)CCC(=C)C(C)C)C)C)(O)C
InChI: InChI=1S/C38H60O7/c1-23(2)24(3)11-12-25(33(41)42)26-15-19-38(9)28-13-14-29-34(4,5)30(45-32(40)22-35(6,43)21-31(39)44-10)17-18-36(29,7)27(28)16-20-37(26,38)8/h23,25-26,29-30,43H,3,11-22H2,1-2,4-10H3,(H,41,42)/t25-,26-,29+,30-,35?,36-,37-,38+/m1/s1
InChIKey: VKMZACSYECLFAU-HNBNAWJQSA-N

Chemical classification

Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Prenol lipids
Sub class: Triterpenoids

Synonymous chemical names:
3a-(3-hydroxy-5-methoxy-3-methyl-1,5-dioxopentyloxy)-24-methylene-5 a -lanost-8-en-21-oic acid, 3a-(3-hydroxy-5-methoxy-3-methyl-1,5-dioxopentyloxy)-24-methylene-5a-lanost-8-en-21-oic acid

Chemical structure download

2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT

Physicochemical properties

Property name	Tool	Property value
Molecular weight (g/mol)	RDKit	628.89
Log P	RDKit	8.04
Topological polar surface area (Å²)	RDKit	110.13
Number of hydrogen bond acceptors	RDKit	6
Number of hydrogen bond donors	RDKit	2
Number of carbon atoms	RDKit	38
Number of heavy atoms	RDKit	45
Number of heteroatoms	RDKit	7
Number of nitrogen atoms	RDKit	0
Number of sulfur atoms	RDKit	0
Number of chiral carbon atoms	RDKit	8
Stereochemical complexity	RDKit	0.21
Number of sp hybridized carbon atoms	RDKit	0
Number of sp² hybridized carbon atoms	RDKit	7
Number of sp³ hybridized carbon atoms	RDKit	31
Fraction of sp³ hybridized carbon atoms (Fsp³)	RDKit	0.82
Shape complexity	RDKit	0.82
Number of rotatable bonds	SwissADME	13
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

Drug-likeness properties

Property name	Tool	Property 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	Bad
Egan filter	RDKit	Bad
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	0.18

ADMET properties

Property name	Tool	Property 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 K_p (Skin permeation, cm/s)	SwissADME	-4.53
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