IMPPAT Phytochemical information: 
Lithospermic acid B
Lithospermic acid B
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](C(=O)O)Cc1ccc(c(c1)O)O)[C@H](O2)c1ccc(c(c1)O)O)O
InChI: InChI=1S/C36H30O16/c37-20-6-1-16(11-24(20)41)13-27(34(45)46)50-29(44)10-5-18-3-9-23(40)33-30(18)31(32(52-33)19-4-8-22(39)26(43)15-19)36(49)51-28(35(47)48)14-17-2-7-21(38)25(42)12-17/h1-12,15,27-28,31-32,37-43H,13-14H2,(H,45,46)(H,47,48)/b10-5+/t27-,28-,31+,32-/m1/s1
InChIKey: SNKFFCBZYFGCQN-VWUOOIFGSA-N
DeepSMILES: O=CO[C@@H]C=O)O))Ccccccc6)O))O))))))))/C=C/cccccc6[C@H]C=O)O[C@@H]C=O)O))Ccccccc6)O))O)))))))))[C@H]O5)cccccc6)O))O)))))))))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1cccc2c1C(C(=O)OCCc1ccccc1)C(c1ccccc1)O2)OCCc1ccccc1
Scaffold Graph/Node level: OC(CCC1CCCC2OC(C3CCCCC3)C(C(O)OCCC3CCCCC3)C12)OCCC1CCCCC1
Scaffold Graph level: CC(CCCC1CCCCC1)CCC1CCCC2CC(C3CCCCC3)C(C(C)CCCC3CCCCC3)C12
Functional groups: c/C=C/C(=O)OC; CC(=O)O; cO; COC(C)=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 b
External chemical identifiers:
CID:CID_6451084; ChEMBL:CHEMBL1615434; ChEBI:CHEBI:134301; ZINC:ZINC000003915684; FDASRS:C1GQ844199; SureChEMBL:SCHEMBL19512041; MolPort-006-395-923
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Lithospermic acid B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 718.62
Log P RDKit 3.33
Topological polar surface area (Å2) RDKit 278.04
Number of hydrogen bond acceptors RDKit 14
Number of hydrogen bond donors RDKit 9
Number of carbon atoms RDKit 36
Number of heavy atoms RDKit 52
Number of heteroatoms RDKit 16
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.11
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 30
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.17
Number of rotatable bonds RDKit 14
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 4
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 4
Total number of rings RDKit 5
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 5
Lithospermic acid B
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.0576879
Lithospermic acid B
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Poorly 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 -7.86
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 3
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
Lithospermic acid B
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000226730IL2800
ENSP00000231449IL4786
ENSP00000296545IL15800
ENSP00000353483MAPK8800
ENSP00000385806KCNMA1786
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.