SALVIANOLIC ACID A


Synonyms	Dan phenolic acid a Salvianolic acid a
Status
Molecule Category	UNKNOWN
UNII	51622542XO


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	YMGFTDKNIWPMGF-UCPJVGPRSA-N
Smiles	O=C(/C=C/c1ccc(O)c(O)c1/C=C/c1ccc(O)c(O)c1)O[C@H](Cc1ccc(O)c(O)c1)C(=O)O
InChI	InChI=1S/C26H22O10/c27-18-7-2-14(11-21(18)30)1-6-17-16(4-9-20(29)25(17)33)5-10-24(32)36-23(26(34)35)13-15-3-8-19(28)22(31)12-15/h1-12,23,27-31,33H,13H2,(H,34,35)/b6-1+,10-5+/t23-/m1/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C26H22O10
Molecular Weight	494.45
AlogP	3.34
Hydrogen Bond Acceptor	9.0
Hydrogen Bond Donor	7.0
Number of Rotational Bond	8.0
Polar Surface Area	184.98
Molecular species	ACID
Aromatic Rings	3.0
Heavy Atoms	36.0

Reference

Journal : J. Nat. Prod.

Title : Anti-lipid-peroxidative principles from Tournefortia sarmentosa.

PubMed ID : 12027757

DOI : 10.1021/np010538y

Year : 2002

Volume : 65

Issue : 5

First Page : 745

Last Page : 747

Authors : Lin YL, Chang YY, Kuo YH, Shiao MS.

Abstract : Using the inhibition of Cu(2+)-induced low-density-lipoprotein (LDL) peroxidation to direct fractionation, four new benzenoids, tournefolal (1), tournefolic acids A (2) and B (3), and B ethyl ester (4), together with salvianolic acid A (5), isosalvianolic acid C (6), lithospermic acid (7), salvianolic acid F (8), and rosmarinic acid (9), were isolated from the stems of Tournefortia sarmentosa. The structures of the new compounds 1-4 were elucidated on the basis of spectral and chemical methods. Furthermore, the anti-LDL-peroxidative activity of the isolated compounds was determined. All isolated compounds exhibited more potent activity than probucol except for salvianolic acid F (8).

Reference

Journal : Bioorg. Med. Chem. Lett.

Title : Natural product inhibitors of protein-protein interactions mediated by Src-family SH2 domains.

PubMed ID : 19427202

DOI : 10.1016/j.bmcl.2009.04.083

Year : 2009

Volume : 19

Issue : 12

First Page : 3305

Last Page : 3309

Authors : Sperl B, Seifert MH, Berg T.

Abstract : In this Letter, we report the natural products salvianolic acid A, salvianolic acid B, and caftaric acid as inhibitors of the protein-protein interactions mediated by the SH2 domains of the Src-family kinases Src and Lck, two established disease targets. Moreover, we propose a binding mode for the inhibitors based on molecular modeling, which will facilitate chemical optimization efforts of these important lead structures for drug discovery.

Reference

Journal : Bioorg. Med. Chem. Lett.

Title : Natural product inhibitors of protein-protein interactions mediated by Src-family SH2 domains.

PubMed ID : 19427202

DOI : 10.1016/j.bmcl.2009.04.083

Year : 2009

Volume : 19

Issue : 12

First Page : 3305

Last Page : 3309

Authors : Sperl B, Seifert MH, Berg T.

Reference

Journal : Bioorg. Med. Chem. Lett.

Title : Natural product inhibitors of protein-protein interactions mediated by Src-family SH2 domains.

PubMed ID : 19427202

DOI : 10.1016/j.bmcl.2009.04.083

Year : 2009

Volume : 19

Issue : 12

First Page : 3305

Last Page : 3309

Authors : Sperl B, Seifert MH, Berg T.

Reference

Journal : Bioorg. Med. Chem.

Title : New natural product carbonic anhydrase inhibitors incorporating phenol moieties.

PubMed ID : 26498393

DOI : 10.1016/j.bmc.2015.10.018

Year : 2015

Volume : 23

Issue : 22

First Page : 7219

Last Page : 7225

Authors : Karioti A, Ceruso M, Carta F, Bilia AR, Supuran CT.

Abstract : Carbonic anhydrases (CAs, EC 4.2.1.1) catalyze the fundamental reaction of CO2 hydration in all living organisms, being actively involved in the regulation of a plethora of patho/physiological conditions. They represent a typical example of enzyme convergent evolution, as six genetically unrelated families of such enzymes were described so far. The need to find selective CA inhibitors (CAIs) triggered the investigation of natural product libraries, which proved to be a valid source of agents with such an activity, as demonstrated for the phenols, polyamines and coumarins. Herein we report an in vitro inhibition study of human (h) CA isoforms hCAs I, II, IV, VII and XII with a panel of natural polyphenols including flavones, flavonols, flavanones, flavanols, isoflavones and depsides, some of which extracted from Quercus ilex and Salvia miltiorrhiza. Several of the investigated derivatives showed interesting inhibition activity and selectivities for inhibiting some important isoforms over the off-target ones hCA I and II.

Reference

Journal : Bioorg. Med. Chem.

Title : New natural product carbonic anhydrase inhibitors incorporating phenol moieties.

PubMed ID : 26498393

DOI : 10.1016/j.bmc.2015.10.018

Year : 2015

Volume : 23

Issue : 22

First Page : 7219

Last Page : 7225

Authors : Karioti A, Ceruso M, Carta F, Bilia AR, Supuran CT.

Reference

Journal : Bioorg. Med. Chem.

Title : New natural product carbonic anhydrase inhibitors incorporating phenol moieties.

PubMed ID : 26498393

DOI : 10.1016/j.bmc.2015.10.018

Year : 2015

Volume : 23

Issue : 22

First Page : 7219

Last Page : 7225

Authors : Karioti A, Ceruso M, Carta F, Bilia AR, Supuran CT.

Assay Description	Organism	Bioactivity
Antioxidant activity against Cu2+-induced lipid peroxidation in human plasma LDL preincubated for 1 hr before Cu2+ challenge	None	590.0 nM
Inhibition of STAT1 SH2 domain at 200 uM	None	41.0 %
Inhibition of STAT3 SH2 domain at 200 uM	None	32.0 %
Inhibition of STAT5b SH2 domain at 200 uM	None	30.2 %
Inhibition of human recombinant carbonic anhydrase 4 preincubated for 15 mins at room temperature/6 hrs at 4 deg C by stopped-flow CO2 hydration assay	Homo sapiens	66.6 nM
Inhibition of human recombinant carbonic anhydrase 7 preincubated for 15 mins at room temperature/6 hrs at 4 deg C by stopped-flow CO2 hydration assay	Homo sapiens	71.4 nM
Inhibition of human recombinant carbonic anhydrase 12 preincubated for 15 mins at room temperature/6 hrs at 4 deg C by stopped-flow CO2 hydration assay	Homo sapiens	39.8 nM

Cross References

Resources	Reference
ChEBI	9017
ChEMBL	CHEMBL457077
DrugBank	DB15246
FDA SRS	51622542XO
KEGG	C10492
PubChem	5281793
SureChEMBL	SCHEMBL19235589
ZINC	ZINC000004098737

CONTENTS

Structure
Chemical and Physical Properties