Secondary metabolite: Officimalonic acid A



Officimalonic acid A
Summary
Molecular formula: C34H50O9
SMILES: OC(=O)CC(=O)O[C@@H]1CC[C@]2([C@H](C1(C)C)C[C@@H]([C@]12C[C@@H](O)[C@]2([C@@](C1=O)(C)CC[C@@H]2[C@@H](C[C@@H]1OC(=O)C(=C1C)C)C)C)O)C
InChI: InChI=1S/C34H50O9/c1-17(13-21-18(2)19(3)28(40)42-21)20-9-11-32(7)29(41)34(16-24(36)33(20,32)8)23(35)14-22-30(4,5)25(10-12-31(22,34)6)43-27(39)15-26(37)38/h17,20-25,35-36H,9-16H2,1-8H3,(H,37,38)/t17-,20-,21+,22+,23+,24-,25-,31+,32+,33+,34-/m1/s1
InChIKey: UDBAOVMCUDEARR-WEEUIZGTSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Organic acids and derivatives
Class: Carboxylic acids and derivatives
Sub class: Tricarboxylic acids and derivatives
Synonymous chemical names:
officimalonic acid a
Chemical structure download



Officimalonic acid A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 602.76
Log P RDKit 4.61
Topological polar surface area (Å2) RDKit 147.43
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 3
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 7
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 5
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 5



Officimalonic acid A
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 3
Ghose filter RDKit Failed
Veber filter RDKit Good
Egan filter RDKit Bad
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 0.29



Officimalonic acid A
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -6.8
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 Yes
P-glycoprotein substrate SwissADME Yes




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