MeFSAT | MeFSAT: Medicinal Fungi Secondary metabolites And Therapeutics

Secondary metabolite: 12b-Acetoxy-3b-hydroxy-7,11,15,23-tetraoxo-lanost-8,20e-diene-26-oic acid

Summary

Molecular formula: C32H42O9
SMILES: CC(=O)O[C@@H]1C(=O)C2=C([C@]3([C@@]1(C)[C@H](CC3=O)/C(=C/C(=O)CC(C(=O)O)C)/C)C)C(=O)C[C@@H]1[C@]2(C)CC[C@@H](C1(C)C)O
InChI: InChI=1S/C32H42O9/c1-15(11-18(34)12-16(2)28(39)40)19-13-23(37)32(8)24-20(35)14-21-29(4,5)22(36)9-10-30(21,6)25(24)26(38)27(31(19,32)7)41-17(3)33/h11,16,19,21-22,27,36H,9-10,12-14H2,1-8H3,(H,39,40)/b15-11+/t16?,19-,21+,22+,27-,30+,31+,32+/m1/s1
InChIKey: NPQPGDYTXMOILM-BOAPTOANSA-N

Chemical classification

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

Synonymous chemical names:
12b-acetoxy-3b-hydroxy-7,11,15,23-tetraoxo-lanost-8,20e-diene-26-oic acid, 12β-Acetoxy-3β-hydroxy- 7,11,15,23-tetraoxolanost- 8,20 E-diene-26-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	570.68
Log P	RDKit	3.8
Topological polar surface area (Å²)	RDKit	152.11
Number of hydrogen bond acceptors	RDKit	8
Number of hydrogen bond donors	RDKit	2
Number of carbon atoms	RDKit	32
Number of heavy atoms	RDKit	41
Number of heteroatoms	RDKit	9
Number of nitrogen atoms	RDKit	0
Number of sulfur atoms	RDKit	0
Number of chiral carbon atoms	RDKit	8
Stereochemical complexity	RDKit	0.25
Number of sp hybridized carbon atoms	RDKit	0
Number of sp² hybridized carbon atoms	RDKit	10
Number of sp³ hybridized carbon atoms	RDKit	22
Fraction of sp³ hybridized carbon atoms (Fsp³)	RDKit	0.69
Shape complexity	RDKit	0.69
Number of rotatable bonds	SwissADME	7
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	1
Lipinski’s rule of 5 filter	RDKit	Passed
Number of Ghose filter violations	RDKit	3
Ghose filter	RDKit	Failed
Veber filter	RDKit	Good
Egan filter	RDKit	Bad
Pfizer’s 3/75 filter	RDKit	Bad
GSK 4/400 filter	RDKit	Bad
Number of Leadlikeness violations	SwissADME	1
Weighted quantitative estimate of drug-likeness (QEDw) score	RDKit	0.36

ADMET properties

Property name	Tool	Property value
Bioavailability score	SwissADME	0.11
Solubility class [ESOL]	SwissADME	Moderately soluble
Solubility class [Silicos-IT]	SwissADME	Moderately soluble
Blood Brain Barrier permeation	SwissADME	No
Gastrointestinal absorption	SwissADME	Low
Log K_p (Skin permeation, cm/s)	SwissADME	-7.83
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	Yes