IMPPAT Phytochemical information: 
Brevifolincarboxylic acid

Brevifolincarboxylic acid
Summary

SMILES: OC(=O)C1CC(=O)c2c1c1c(O)c(O)c(cc1c(=O)o2)O
InChI: InChI=1S/C13H8O8/c14-5-2-4-7(10(17)9(5)16)8-3(12(18)19)1-6(15)11(8)21-13(4)20/h2-3,14,16-17H,1H2,(H,18,19)
InChIKey: JFJWMFPFMLRLMI-UHFFFAOYSA-N
DeepSMILES: OC=O)CCC=O)cc5ccO)cO)ccc6c=O)o%10))))O
Scaffold Graph/Node/Bond level: O=C1CCc2c1oc(=O)c1ccccc21
Scaffold Graph/Node level: OC1CCC2C3CCCCC3C(O)OC12
Scaffold Graph level: CC1CC2C(C)CCC2C2CCCCC12
Functional groups: CC(=O)O; cC(=O)C; cO; c=O; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isocoumarins and derivatives
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Isocoumarins
Synonymous chemical names:
brevifolin carboxylic acid, brevifolin-carboxylic-acid
External chemical identifiers:
CID:CID_9838995; SureChEMBL:SCHEMBL1499932; MolPort-044-727-228
Chemical structure download


Brevifolincarboxylic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 292.2
Log P RDKit 0.66
Topological polar surface area (Å2) RDKit 145.27
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 13
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.08
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.15
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
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 3


Brevifolincarboxylic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Bad
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.56


Brevifolincarboxylic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.38
Number of PAINS structural alerts SwissADME 1
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 No
P-glycoprotein substrate SwissADME No