(2R)-2-{[(2E)-3-[(2R,3R)-3-{[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoic acid

• ChemBase ID: 179898
• Molecular Formular: C36H30O16
• Molecular Mass: 718.6138
• Monoisotopic Mass: 718.15338488
• SMILES: [C@@H]1([C@@H](Oc2c1c(/C=C/C(=O)O[C@@H](C(=O)O)Cc1cc(c(cc1)O)O)ccc2O)c1cc(c(cc1)O)O)C(=O)OC(C(=O)O)Cc1cc(c(cc1)O)O
• Canonical SMILES: O=C(O[C@@H](C(=O)O)Cc1ccc(c(c1)O)O)/C=C/c1ccc(c2c1[C@@H](C(=O)OC(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-RDHSGEKBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-{[(2E)-3-[(2R,3R)-3-{[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoic acid
• IUPAC Traditional name: (2R)-2-{[(2E)-3-[(2R,3R)-3-{[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoic acid
• Synonyms: Salvianolic acid B

Database IDs

• CAS Number: 115939-25-8
• PubChem SID: 164235808
• PubChem CID: 6441188

CALCULATED PROPERTIES

• Acid pKa: 2.7735696
• H Acceptors: 14
• H Donor: 9
• LogD (pH = 5.5): 0.19945902
• LogD (pH = 7.4): -1.9595973
• Log P: 4.987508
• Molar Refractivity: 177.0009 cm^3
• Polarizability: 68.05364 Å^3
• Polar Surface Area: 278.04 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Apoptosis inhibitor; Improve the energy metabolism; Reduce lipid peroxides; Scavenge free radicals

Product Information

• Biological Source: Constit. of Salvia miltiorrhiza
• Application(s): Antioxidant; Used for treatment of cerebrovascular disorders

REFERENCES

• PLoS One. 2007 Dec 19; 2(12):e1321.
• 1. Chen YH, Du GH, Zhang JT. Salvianolic acid B protects brain against injuries caused by ischemia-reperfusion in rats. Acta Pharmacol Sin. 2000 May;21(5):463-6.
• 2. Liu CL, Xie LX, Li M, Durairajan SS, Goto S, Huang JD. Salvianolic acid B inhibits hydrogen peroxide-induced endothelial cell apoptosis through regulating PI3K/Akt signaling.