MeFSAT | MeFSAT: Medicinal Fungi Secondary metabolites And Therapeutics

Secondary metabolite: Officimalonic acid C

Summary

Molecular formula: C34H48O9
SMILES: OC(=O)CC(=O)O[C@@H]1CC[C@]2([C@H](C1(C)C)CC(=O)C1=C2C[C@@H](O)[C@]23[C@@]1(C)CC[C@@H]3[C@H](C)C[C@]1(OC2)OC(=O)[C@H]([C@@H]1C)C)C
InChI: InChI=1S/C34H48O9/c1-17-15-34(19(3)18(2)29(40)43-34)41-16-33-20(17)8-11-32(33,7)28-21(12-24(33)36)31(6)10-9-25(42-27(39)14-26(37)38)30(4,5)23(31)13-22(28)35/h17-20,23-25,36H,8-16H2,1-7H3,(H,37,38)/t17-,18+,19+,20-,23+,24-,25-,31-,32+,33+,34+/m1/s1
InChIKey: JVTKEEUUSBPFFJ-NGPOTDMGSA-N

Chemical classification

Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Steroids and steroid derivatives
Sub class: Steroid lactones

Synonymous chemical names:
officimalonic acid c

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	600.75
Log P	RDKit	4.83
Topological polar surface area (Å²)	RDKit	136.43
Number of hydrogen bond acceptors	RDKit	8
Number of hydrogen bond donors	RDKit	2
Number of carbon atoms	RDKit	34
Number of heavy atoms	RDKit	43
Number of heteroatoms	RDKit	9
Number of nitrogen atoms	RDKit	0
Number of sulfur atoms	RDKit	0
Number of chiral carbon atoms	RDKit	11
Stereochemical complexity	RDKit	0.32
Number of sp hybridized carbon atoms	RDKit	0
Number of sp² hybridized carbon atoms	RDKit	6
Number of sp³ hybridized carbon atoms	RDKit	28
Fraction of sp³ hybridized carbon atoms (Fsp³)	RDKit	0.82
Shape complexity	RDKit	0.82
Number of rotatable bonds	SwissADME	4
Number of aliphatic carbocycles	RDKit	4
Number of aliphatic heterocycles	RDKit	2
Number of aliphatic rings	RDKit	6
Number of aromatic carbocycles	RDKit	0
Number of aromatic heterocycles	RDKit	0
Number of aromatic rings	RDKit	0
Total number of rings	RDKit	6
Number of saturated carbocycles	RDKit	2
Number of saturated heterocycles	RDKit	2
Number of saturated rings	RDKit	4
Number of Smallest Set of Smallest Rings (SSSR)	RDKit	6

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
Pfizer’s 3/75 filter	RDKit	Bad
GSK 4/400 filter	RDKit	Bad
Number of Leadlikeness violations	SwissADME	2
Weighted quantitative estimate of drug-likeness (QEDw) score	RDKit	0.34

ADMET properties

Property name	Tool	Property 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 K_p (Skin permeation, cm/s)	SwissADME	-6.42
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	No
P-glycoprotein substrate	SwissADME	Yes