Showing metabocard for Rosmarinic acid (BMDB0003572)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:05:23 UTC
Update Date2020-05-11 20:03:12 UTC
BMDB IDBMDB0003572
Secondary Accession Numbers
  • BMDB03572
Metabolite Identification
Common NameRosmarinic acid
DescriptionRosmarinic acid, also known as rosmarinate or rosemary acid, belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Based on a literature review a significant number of articles have been published on Rosmarinic acid.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2R)-O-Caffeoyl-3-(3,4-dihydroxyphenyl)lactic acidChEBI
(2R)-O-Caffeoyl-3-(3,4-dihydroxyphenyl)lactateGenerator
RosmarinateGenerator
Rosemary acidHMDB
Rosmarinic acid, (R-(e))-isomerHMDB
(R)-RosmarinateHMDB
Labiatenic acidHMDB
Labiatic acidHMDB
Rosemaric acidHMDB
trans-Rosmarinic acidHMDB
(Z)-Rosmarinic acidHMDB
Rosmarinic acidChEBI
Chemical FormulaC18H16O8
Average Molecular Weight360.3148
Monoisotopic Molecular Weight360.084517488
IUPAC Name(2R)-3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid
Traditional Namerosemary acid
CAS Registry Number537-15-5
SMILES
OC(=O)[C@@H](CC1=CC(O)=C(O)C=C1)OC(=O)\C=C\C1=CC(O)=C(O)C=C1
InChI Identifier
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
InChI KeyDOUMFZQKYFQNTF-WUTVXBCWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentCoumaric acids and derivatives
Alternative Parents
Substituents
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • 3-phenylpropanoic-acid
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Monocyclic benzene moiety
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.57ALOGPS
logP3ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)3.13ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area144.52 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity90.95 m³·mol⁻¹ChemAxon
Polarizability34.55 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-00kb-1889000000-a18403fdf27acdd9420aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00kb-1889000000-a18403fdf27acdd9420aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03k9-0900000000-0bfd48de4c7d7947465fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0a59-6429037000-febdf15ccc07a12300c9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0901000000-f29409b402b063dcbebdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0bt9-0907000100-ececf6d2ede2e8193b9bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03e9-0900000000-14bb8ce94558a85b706cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0902000000-f3cc2fa86fc00ea8e474View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-0dac983721970230a210View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0439000000-38b13aa5bfab28c4d0c2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0900000000-383db44d2370c9662666View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-008i-0679000000-629ad81e5a4aa4a45cd9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0900000000-f099de2a6e6ab011d21bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0900000000-529a6653ec4eebdd8eebView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0239-1900000000-8bed95d3ae91d9873e98View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-0902000000-36563722d30feeb69ae3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-d32896fadf8e7c5c5fa4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-01qi-0920000000-d260d2efdd9728ef5c32View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-03di-0901000000-c16c277f268b2702b889View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-78c63d5f30f84af872c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-5952242833f0961865d1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-08fr-0904000000-1e0e6099d149a663ad7eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-2900000000-7836cebf0e5a43bbc84fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0819000000-20e9707f2681dfaa1a77View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0902000000-a28b547c92e2012a4b54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05gi-2900000000-7a9099cde66c5c7e5309View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-0917000000-020d7427c4eb0534eba7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0901000000-2beb88c288aa75c18319View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fr-0900000000-a99d2e96b7197132aef0View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen Locations
  • Fibroblasts
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0003572
DrugBank IDNot Available
Phenol Explorer Compound ID461
FooDB IDFDB002427
KNApSAcK IDC00002770
Chemspider ID4445104
KEGG Compound IDC01850
BioCyc IDCPD-6981
BiGG IDNot Available
Wikipedia LinkRosmarinic_acid
METLIN ID6960
PubChem Compound5281792
PDB IDNot Available
ChEBI ID50371
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available