IMPPAT Phytochemical information: 
Lithospermic acid
Lithospermic acid
Summary

SMILES: O=C(O[C@@H](C(=O)O)Cc1ccc(c(c1)O)O)/C=C/c1ccc(c2c1[C@H](C(=O)O)[C@H](O2)c1ccc(c(c1)O)O)O
InChI: InChI=1S/C27H22O12/c28-15-5-1-12(9-18(15)31)10-20(26(34)35)38-21(33)8-4-13-2-7-17(30)25-22(13)23(27(36)37)24(39-25)14-3-6-16(29)19(32)11-14/h1-9,11,20,23-24,28-32H,10H2,(H,34,35)(H,36,37)/b8-4+/t20-,23+,24-/m1/s1
InChIKey: UJZQBMQZMKFSRV-RGKBJLTCSA-N
DeepSMILES: O=CO[C@@H]C=O)O))Ccccccc6)O))O))))))))/C=C/cccccc6[C@H]C=O)O))[C@H]O5)cccccc6)O))O)))))))))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1cccc2c1CC(c1ccccc1)O2)OCCc1ccccc1
Scaffold Graph/Node level: OC(CCC1CCCC2OC(C3CCCCC3)CC12)OCCC1CCCCC1
Scaffold Graph level: CC(CCCC1CCCCC1)CCC1CCCC2CC(C3CCCCC3)CC12
Functional groups: c/C=C/C(=O)OC; cO; CC(=O)O; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: 2-arylbenzofuran flavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Neolignans
Synonymous chemical names:
lithospermic acid
External chemical identifiers:
CID:CID_6441498; ChEMBL:CHEMBL518243; ZINC:ZINC000004097774; FDASRS:100IP83JAC; SureChEMBL:SCHEMBL13284084; MolPort-020-005-934
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Lithospermic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 538.46
Log P RDKit 2.77
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 27
Number of heavy atoms RDKit 39
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.11
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 23
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.15
Number of rotatable bonds RDKit 9
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 3
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
Lithospermic 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 2
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 0.13
Lithospermic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -7.61
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 No