Identification

PhytoHub ID
PHUB000634
Name
Rosmarinic acid
Systematic Name
Not Available
Synonyms
Not Available
CAS Number
Not Available
Average Mass
360.318
Monoisotopic Mass
360.084517475
Chemical Formula
C18H16O8
IUPAC Name
(S)-rosmarinic acid
InChI Key
DOUMFZQKYFQNTF-GIZXNFQBSA-N
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-/m0/s1
SMILES
OC(=O)[[email protected]](CC1=CC(O)=C(O)C=C1)OC(=O)\C=C\C1=CC(O)=C(O)C=C1
Structure

Calculated Properties

Solubility (ALOGPS)
4.07e-02 g/l
LogS (ALOGPS)
-3.95
LogP (ALOGPS)
2.57
Hydrogen Acceptors
7
Hydrogen Donors
5
Rotatable Bond Count
7
Polar Surface Area
144.52
Refractivity
90.9501
Polarizability
34.34113577057401
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
-6.283762279508309
pKa (strongest acidic)
3.1312932183061957
Number of Rings
2
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Precursor

Family
Polyphenols
Class
Phenolic acids
Sub-class
Hydroxycinnamic acids

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Cinnamic acids and derivatives
Super-class
Phenylpropanoids and polyketides
Sub-class
Hydroxycinnamic acids and derivatives
Direct Parent Name
Coumaric acids and derivatives
Alternative Parent Names
["1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "Carbonyl compounds", "Carboxylic acids", "Catechols", "Cinnamic acid esters", "Dicarboxylic acids and derivatives", "Enoate esters", "Fatty acid esters", "Hydrocarbon derivatives", "Organic oxides", "Phenylpropanoic acids", "Styrenes"]
External Descriptor Annotations
["rosmarinic acid"]
Substituent Names
["1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "3-phenylpropanoic-acid", "Alpha,beta-unsaturated carboxylic ester", "Aromatic homomonocyclic compound", "Benzenoid", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Carboxylic acid ester", "Catechol", "Cinnamic acid ester", "Coumaric acid or derivatives", "Dicarboxylic acid or derivatives", "Enoate ester", "Fatty acid ester", "Fatty acyl", "Hydrocarbon derivative", "Monocyclic benzene moiety", "Organic oxide", "Organic oxygen compound", "Organooxygen compound", "Phenol", "Styrene"]

Spectra

Record IDSourceDescriptionView
BML82096MassBankLC-ESI-QTOF Spectrum - -, unspecifiedView Spectra
PR040215MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, [M-H]-View Spectra
PR040216MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, [2M-H]-View Spectra
PR040217MassBankLC-ESI-QTOF Spectrum - 30 V, [M-H]-View Spectra
PR040218MassBankLC-ESI-QTOF Spectrum - 30 V, [2M-H]-View Spectra
PR040219MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, [M+Na]+View Spectra
PR040220MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, [M+H]+View Spectra
PR040221MassBankLC-ESI-QTOF Spectrum - 30 V, [2M+Na]+View Spectra
PR100686MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra
PS045201ReSpectN/A Spectrum - 10, [M+H]+View Spectra
PS045202ReSpectN/A Spectrum - 20, [M+H]+View Spectra
PS045203ReSpectN/A Spectrum - 30, [M+H]+View Spectra
PS045204ReSpectN/A Spectrum - 40, [M+H]+View Spectra
PS045207ReSpectN/A Spectrum - 10, [M-H]-View Spectra
PS045208ReSpectN/A Spectrum - 20, [M-H]-View Spectra
PS045209ReSpectN/A Spectrum - 30, [M-H]-View Spectra
PS045210ReSpectN/A Spectrum - 40, [M-H]-View Spectra

Food Sources

Food Sources of its Precursor(s)

No food source information available of its precursor(s)

Metabolism

PrecursorMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Rosmarinic acid Caffeic acidraturineNot AvailableNot AvailableNot AvailableNot AvailableC9H8O4180.042258738 Publications
Rosmarinic acid Coumaric acid (m-)ratplasma, urineNot AvailableNot AvailableNot AvailableNot AvailableC9H8O3164.047344118 Publications
Rosmarinic acid 3-(3'-Hydroxyphenyl)propionic acidratplasma, urineNot AvailableNot AvailableNot AvailableNot AvailableC9H10O3166.062994182 Publications
Rosmarinic acid Ferulic acid-4'-sulfateratplasma, urineNot AvailableNot AvailableNot AvailableNot AvailableC10H10O7S274.014723836 Publications
Rosmarinic acid caffeic acid-4-O-sulfateraturineNot AvailableNot AvailableNot AvailableNot AvailableC9H8O7S259.999073772 Publications
Rosmarinic acid m-coumaric acid 3-O-sulfateratplasma, urineNot AvailableNot AvailableNot AvailableNot AvailableC9H8O5S228.009244532 Publications

Inter-Individual Variations Metabolism

No inter-individual variations available

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