IMPPAT Phytochemical information: 
Brainic acid
Brainic acid
Summary

SMILES: OC(=O)/C=C/c1ccc(c2c1[C@@H](C(=O)O[C@@H]1CC(=C[C@H]([C@H]1O)O)C(=O)O)[C@H](O2)c1ccc(c(c1)O)O)O
InChI: InChI=1S/C25H22O12/c26-13-4-2-11(7-15(13)28)22-20(19-10(3-6-18(30)31)1-5-14(27)23(19)37-22)25(35)36-17-9-12(24(33)34)8-16(29)21(17)32/h1-8,16-17,20-22,26-29,32H,9H2,(H,30,31)(H,33,34)/b6-3+/t16-,17-,20-,21-,22-/m1/s1
InChIKey: IJAGKEKOJGWANE-KCBWXHRDSA-N
DeepSMILES: OC=O)/C=C/cccccc6[C@@H]C=O)O[C@@H]CC=C[C@H][C@H]6O))O)))C=O)O)))))))[C@H]O5)cccccc6)O))O)))))))))O
Scaffold Graph/Node/Bond level: O=C(OC1CC=CCC1)C1c2ccccc2OC1c1ccccc1
Scaffold Graph/Node level: OC(OC1CCCCC1)C1C2CCCCC2OC1C1CCCCC1
Scaffold Graph level: CC(CC1CCCCC1)C1C2CCCCC2CC1C1CCCCC1
Functional groups: c/C=C/C(=O)O; COC(C)=O; CC(C(=O)O)=CC; CO; cOC; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: 2-arylbenzofuran flavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
Synonymous chemical names:
brainic acid
External chemical identifiers:
CID:CID_10436502; ZINC:ZINC000137310554
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Brainic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 514.44
Log P RDKit 1.17
Topological polar surface area (Å2) RDKit 211.28
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 25
Number of heavy atoms RDKit 37
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.2
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 19
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.24
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
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 4
Brainic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 1
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.16
Brainic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.98
Number of PAINS structural alerts SwissADME 1
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 No
P-glycoprotein substrate SwissADME Yes