MeFSAT | MeFSAT: Medicinal Fungi Secondary metabolites And Therapeutics

Secondary metabolite: 3β,5α-Dihydroxy-(22e,24r)-ergosta-22-en-7-one-6β-yl oleate

Summary

Molecular formula: C46H78O5
SMILES: CCCCCCCC/C=CCCCCCCCC(=O)O[C@@H]1C(=O)[C@H]2[C@@H]3CC[C@@H]([C@@]3(C)CC[C@@H]2[C@@]2([C@]1(O)C[C@@H](O)CC2)C)[C@@H](/C=C/[C@@H](C(C)C)C)C
InChI: InChI=1S/C46H78O5/c1-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-40(48)51-43-42(49)41-38-27-26-37(35(5)25-24-34(4)33(2)3)44(38,6)30-29-39(41)45(7)31-28-36(47)32-46(43,45)50/h15-16,24-25,33-39,41,43,47,50H,8-14,17-23,26-32H2,1-7H3/b16-15-,25-24+/t34-,35+,36-,37+,38-,39-,41-,43+,44+,45+,46-/m0/s1
InChIKey: YEFGYSYQDJVEFQ-NFCNPGOKSA-N

Chemical classification

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

Synonymous chemical names:
3β,5α-dihydroxy-(22e,24r)-ergosta-22-en-7-one-6β-yl oleate

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	711.12
Log P	RDKit	11.34
Topological polar surface area (Å²)	RDKit	83.83
Number of hydrogen bond acceptors	RDKit	5
Number of hydrogen bond donors	RDKit	2
Number of carbon atoms	RDKit	46
Number of heavy atoms	RDKit	51
Number of heteroatoms	RDKit	5
Number of nitrogen atoms	RDKit	0
Number of sulfur atoms	RDKit	0
Number of chiral carbon atoms	RDKit	11
Stereochemical complexity	RDKit	0.24
Number of sp hybridized carbon atoms	RDKit	0
Number of sp² hybridized carbon atoms	RDKit	6
Number of sp³ hybridized carbon atoms	RDKit	40
Fraction of sp³ hybridized carbon atoms (Fsp³)	RDKit	0.87
Shape complexity	RDKit	0.87
Number of rotatable bonds	SwissADME	21
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	4
Number of saturated heterocycles	RDKit	0
Number of saturated rings	RDKit	4
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
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	0.07

ADMET properties

Property name	Tool	Property value
Bioavailability score	SwissADME	0.17
Solubility class [ESOL]	SwissADME	Insoluble
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	-0.95
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