Secondary metabolite: 1,2-Diacetylsphingosine



1,2-Diacetylsphingosine
Summary
Molecular formula: C22H43NO4
SMILES: CCCCCCCCCCCCCCC[C@H]([C@@H](NC(=O)C)COC(=O)C)O
InChI: InChI=1S/C22H43NO4/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-22(26)21(23-19(2)24)18-27-20(3)25/h21-22,26H,4-18H2,1-3H3,(H,23,24)/t21-,22+/m0/s1
InChIKey: IJUQYYAQRYPAMG-FCHUYYIVSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Organic acids and derivatives
Class: Carboxylic acids and derivatives
Sub class: Carboxylic acid derivatives
Synonymous chemical names:
1,2-diacetylsphingosine
Chemical structure download



1,2-Diacetylsphingosine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 385.59
Log P RDKit 4.9
Topological polar surface area (Å2) RDKit 75.63
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.09
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 2
Number of sp3 hybridized carbon atoms RDKit 20
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.91
Shape complexity RDKit 0.91
Number of rotatable bonds SwissADME 20
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 0
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 0



1,2-Diacetylsphingosine
Drug-likeness properties
Property nameToolProperty 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 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 0.26



1,2-Diacetylsphingosine
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -3.94
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes




Designed by R.P. Vivek-Ananth, M Karthikeyan and Ajaya Kumar Sahoo