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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5 entries where ROA is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	42
Chiral Atom Count	1
Bond Count	43
Aromatic Bond Count	12

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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
Synonyms	Rosmarinic 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
Formula	C₁₈ H₁₆ O₈
Molecular Weight	360.315
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	O=C(O)C(OC(=O)\C=C\c1ccc(O)c(O)c1)Cc2cc(O)c(O)cc2
SMILES	CACTVS	3.385	OC(=O)[CH](Cc1ccc(O)c(O)c1)OC(=O)C=Cc2ccc(O)c(O)c2
SMILES	OpenEye OEToolkits	1.7.6	c1cc(c(cc1CC(C(=O)O)OC(=O)C=Cc2ccc(c(c2)O)O)O)O
Canonical SMILES	CACTVS	3.385	OC(=O)[C@@H](Cc1ccc(O)c(O)c1)OC(=O)\C=C\c2ccc(O)c(O)c2
Canonical SMILES	OpenEye OEToolkits	1.7.6	c1cc(c(cc1C[C@H](C(=O)O)OC(=O)/C=C/c2ccc(c(c2)O)O)O)O
InChI	InChI	1.03	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
InChIKey	InChI	1.03	DOUMFZQKYFQNTF-WUTVXBCWSA-N

Drug Info: DrugBank

DrugBank ID	DB16865
Name	Rosmarinic acid
Groups	investigational
Synonyms	Labiatic acid Rosemary acid Labiatenic acid Rosmarinic acid
Categories	Acids, Carbocyclic Aldehyde Reductase, antagonists & inhibitors Analgesics Analgesics, Non-Narcotic Anti-Inflammatory Agents Anti-Inflammatory Agents, Non-Steroidal Antioxidants Antiplatelet agents Antirheumatic Agents Benzene Derivatives Benzoates Biological Factors Cinnamates Compounds used in a research, industrial, or household setting Depsides Enzyme Inhibitors Hematologic Agents Hydroxy Acids Hydroxybenzoates Peripheral Nervous System Agents Phenols Protease Inhibitors Protective Agents Sensory System Agents Serine Protease Inhibitors
CAS number	20283-92-5

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Tyrosinase	MLLAVLYCLLWSFQTSAGHFPRACVSSKNLMEKECCPPWSGDRSPCGQLS...	unknown	inhibitor
Induced myeloid leukemia cell differentiation protein Mcl-1	MFGLKRNAVIGLNLYCGGAGLGAGSGGATRPGGRLLATEKEASARREIGG...	unknown	inhibitor

Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682