ROA

(2R)-3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid

Created: 2011-09-02
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count42
Chiral Atom Count1
Bond Count43
Aromatic Bond Count12
2D diagram of ROA
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Chemical Component Summary

Name(2R)-3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid
SynonymsRosmarinic acid
Systematic Name (OpenEye OEToolkits)(2R)-3-[3,4-bis(oxidanyl)phenyl]-2-[(E)-3-[3,4-bis(oxidanyl)phenyl]prop-2-enoyl]oxy-propanoic acid
FormulaC18 H16 O8
Molecular Weight360.315
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01O=C(O)C(OC(=O)\C=C\c1ccc(O)c(O)c1)Cc2cc(O)c(O)cc2
SMILESCACTVS3.385OC(=O)[CH](Cc1ccc(O)c(O)c1)OC(=O)C=Cc2ccc(O)c(O)c2
SMILESOpenEye OEToolkits1.7.6c1cc(c(cc1CC(C(=O)O)OC(=O)C=Cc2ccc(c(c2)O)O)O)O
Canonical SMILESCACTVS3.385 OC(=O)[C@@H](Cc1ccc(O)c(O)c1)OC(=O)\C=C\c2ccc(O)c(O)c2
Canonical SMILESOpenEye OEToolkits1.7.6 c1cc(c(cc1C[C@H](C(=O)O)OC(=O)/C=C/c2ccc(c(c2)O)O)O)O
InChIInChI1.03 InChI=1S/C18H16O8/c19-12-4-1-10(7-14(12)21)3-6-17(23)26-16(18(24)25)9-11-2-5-13(20)15(22)8-11/h1-8,16,19-22H,9H2,(H,24,25)/b6-3+/t16-/m1/s1
InChIKeyInChI1.03 DOUMFZQKYFQNTF-WUTVXBCWSA-N

Drug Info: DrugBank

DrugBank IDDB16865 
NameRosmarinic acid
Groups investigational
Synonyms
  • Rosemary acid
  • Labiatenic acid
  • Labiatic acid
  • Rosmarinic acid
Categories
  • Acids, Carbocyclic
  • Aldehyde Reductase, antagonists & inhibitors
  • Analgesics
  • Analgesics, Non-Narcotic
  • Anti-Inflammatory Agents
CAS number20283-92-5

Related Resource References

Resource NameReference
Pharos CHEMBL324842
PubChem 5281792
ChEMBL CHEMBL324842
ChEBI CHEBI:50371, CHEBI:92370