Showing Compound Card for Rosmarinic acid (CDB004963)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-04-17 18:55:04 UTC
Updated at2020-11-18 16:39:07 UTC
CannabisDB IDCDB004963
Secondary Accession NumbersNot Available
Cannabis Compound 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. A stereoisomer of rosmarinic acid having (R)-configuration. Rosmarinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Rosmarinic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
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 Weight360.31
Monoisotopic Molecular Weight360.0845
IUPAC Name(2R)-3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid
Traditional Namerosemary acid
CAS Registry Number20283-92-5
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
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateNot Available
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSRosmarinic acid, 5 TMS, GC-MS Spectrumsplash10-00kb-1889000000-a18403fdf27acdd9420aSpectrum
GC-MSRosmarinic acid, non-derivatized, GC-MS Spectrumsplash10-00kb-1889000000-a18403fdf27acdd9420aSpectrum
Predicted GC-MSRosmarinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03k9-0900000000-0bfd48de4c7d7947465fSpectrum
Predicted GC-MSRosmarinic acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a59-6429037000-febdf15ccc07a12300c9Spectrum
Predicted GC-MSRosmarinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0901000000-f29409b402b063dcbebd2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0bt9-0907000100-ececf6d2ede2e8193b9b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03e9-0900000000-14bb8ce94558a85b706c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0902000000-f3cc2fa86fc00ea8e4742017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-0dac983721970230a2102017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0439000000-38b13aa5bfab28c4d0c22017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0900000000-383db44d2370c96626662017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-008i-0679000000-629ad81e5a4aa4a45cd92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0900000000-f099de2a6e6ab011d21b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0900000000-529a6653ec4eebdd8eeb2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0239-1900000000-8bed95d3ae91d9873e982021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-0902000000-36563722d30feeb69ae32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-d32896fadf8e7c5c5fa42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-01qi-0920000000-d260d2efdd9728ef5c322021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-03di-0901000000-c16c277f268b2702b8892021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-78c63d5f30f84af872c62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-5952242833f0961865d12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-08fr-0904000000-1e0e6099d149a663ad7e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-2900000000-7836cebf0e5a43bbc84f2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0819000000-20e9707f2681dfaa1a772016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0902000000-a28b547c92e2012a4b542016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05gi-2900000000-7a9099cde66c5c7e53092016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-0917000000-020d7427c4eb0534eba72016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0901000000-2beb88c288aa75c183192016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fr-0900000000-a99d2e96b7197132aef02016-08-04View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0003572
DrugBank IDNot Available
Phenol Explorer Compound ID461
FoodDB 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
General ReferencesNot Available