MeFSAT | MeFSAT: Medicinal Fungi Secondary metabolites And Therapeutics

Secondary metabolite: Zygosporin D

Summary

Molecular formula: C28H35NO5
SMILES: C=C1[C@@H](C)[C@H]2[C@H](Cc3ccccc3)NC(=O)C32C([C@@H]1O)/C=C/C[C@H](C)C(=O)[C@](/C=C/[C@H]3O)(C)O
InChI: InChI=1S/C28H35NO5/c1-16-9-8-12-20-24(31)18(3)17(2)23-21(15-19-10-6-5-7-11-19)29-26(33)28(20,23)22(30)13-14-27(4,34)25(16)32/h5-8,10-14,16-17,20-24,30-31,34H,3,9,15H2,1-2,4H3,(H,29,33)/b12-8+,14-13+/t16-,17+,20?,21-,22+,23-,24+,27+,28?/m0/s1
InChIKey: DMUBZPWTFAPROZ-PITCCCLTSA-N

Chemical classification

Kingdom: Organic compounds
Super class: Alkaloids and derivatives
Class: Cytochalasans

Synonymous chemical names:
zygosporin d

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	465.59
Log P	RDKit	2.35
Topological polar surface area (Å²)	RDKit	106.86
Number of hydrogen bond acceptors	RDKit	5
Number of hydrogen bond donors	RDKit	4
Number of carbon atoms	RDKit	28
Number of heavy atoms	RDKit	34
Number of heteroatoms	RDKit	6
Number of nitrogen atoms	RDKit	1
Number of sulfur atoms	RDKit	0
Number of chiral carbon atoms	RDKit	9
Stereochemical complexity	RDKit	0.32
Number of sp hybridized carbon atoms	RDKit	0
Number of sp² hybridized carbon atoms	RDKit	14
Number of sp³ hybridized carbon atoms	RDKit	14
Fraction of sp³ hybridized carbon atoms (Fsp³)	RDKit	0.5
Shape complexity	RDKit	0.5
Number of rotatable bonds	SwissADME	2
Number of aliphatic carbocycles	RDKit	2
Number of aliphatic heterocycles	RDKit	1
Number of aliphatic rings	RDKit	3
Number of aromatic carbocycles	RDKit	1
Number of aromatic heterocycles	RDKit	0
Number of aromatic rings	RDKit	1
Total number of rings	RDKit	4
Number of saturated carbocycles	RDKit	1
Number of saturated heterocycles	RDKit	1
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	0
Lipinski’s rule of 5 filter	RDKit	Passed
Number of Ghose filter violations	RDKit	0
Ghose filter	RDKit	Passed
Veber filter	RDKit	Good
Pfizer’s 3/75 filter	RDKit	Good
GSK 4/400 filter	RDKit	Bad
Number of Leadlikeness violations	SwissADME	1
Weighted quantitative estimate of drug-likeness (QEDw) score	RDKit	0.5

ADMET properties

Property name	Tool	Property value
Bioavailability score	SwissADME	0.55
Solubility class [ESOL]	SwissADME	Moderately soluble
Solubility class [Silicos-IT]	SwissADME	Moderately soluble
Blood Brain Barrier permeation	SwissADME	No
Gastrointestinal absorption	SwissADME	High
Log K_p (Skin permeation, cm/s)	SwissADME	-7.6
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