Secondary metabolite: 15-Deoxyoxalicine B



15-Deoxyoxalicine B
Summary
Molecular formula: C30H33NO6
SMILES: O=C1CC[C@]2(CO1)[C@H]1CC=C([C@@]3([C@]1(C)CC[C@@]2(O)C(=C)C)Oc1c(C3)c(=O)oc(c1)c1cccnc1)C
InChI: InChI=1S/C30H33NO6/c1-18(2)29(34)12-11-27(4)24(28(29)10-9-25(32)35-17-28)8-7-19(3)30(27)15-21-23(37-30)14-22(36-26(21)33)20-6-5-13-31-16-20/h5-7,13-14,16,24,34H,1,8-12,15,17H2,2-4H3/t24-,27+,28-,29+,30-/m0/s1
InChIKey: FIWRZQROYVDBSG-GBLYIOFISA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Prenol lipids
Sub class: Terpene lactones
Synonymous chemical names:
15-deoxyoxalicine b
Chemical structure download



15-Deoxyoxalicine B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 503.6
Log P RDKit 4.77
Topological polar surface area (Å2) RDKit 98.86
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 37
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.17
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 15
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 2
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 2
Total number of rings RDKit 6
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 6



15-Deoxyoxalicine B
Drug-likeness properties
Property nameToolProperty 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 2
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 1
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.47



15-Deoxyoxalicine B
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 -6.92
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




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