ChemFOnt: Showing chemical card for 3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid (CFc000105350)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 21:22:15 UTC

Chemfont ID

CFc000105350

Molecule Identification

Common Name

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

Definition

3-(3,4-dihydroxyphenyl)-2-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate. It is generated by Liver carboxylesterase 1 (P23141) enzyme via a hydrolysis-of-carboxylic-acid-ester-pattern1 reaction. This hydrolysis-of-carboxylic-acid-ester-pattern1 occurs in humans and human gut microbiota.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2R)-O-Caffeoyl-3-(3,4-dihydroxyphenyl)lactic acid	ChEBI
(2R)-O-Caffeoyl-3-(3,4-dihydroxyphenyl)lactate	Generator
Rosmarinate	Generator
Rosemary acid	HMDB
Rosmarinic acid, (R-(e))-isomer	HMDB
(R)-Rosmarinate	HMDB
Labiatenic acid	HMDB
Labiatic acid	HMDB
Rosemaric acid	HMDB
trans-Rosmarinic acid	HMDB
(Z)-Rosmarinic acid	HMDB
Rosmarinic acid	ChEBI

Chemical Formula

C₁₈H₁₆O₈

Average Molecular Weight

360.3148

Monoisotopic Molecular Weight

360.084517488

IUPAC Name

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

Traditional Name

rosemary acid

CAS Registry Number

20283-92-5

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 Key

DOUMFZQKYFQNTF-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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

rosmarinic acid (CHEBI:50371 )

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0124941)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.041 g/L	ALOGPS
logP	2.57	ALOGPS
logP	3	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	3.13	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	90.95 m³·mol⁻¹	ChemAxon
Polarizability	34.55 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0003572

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Rosmarinic_acid

METLIN ID

6960

PubChem Compound

5281792

PDB ID

Not Available

ChEBI ID

50371

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid (CFc000105350)

MOL for CFc000105350 (3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid)

3D MOL for CFc000105350 (3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid)

3D SDF for CFc000105350 (3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid)

3D-SDF for CFc000105350 (3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid)

PDB for CFc000105350 (3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid)

3D PDB for CFc000105350 (3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid)

SMILES for CFc000105350 (3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid)

INCHI for CFc000105350 (3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid)

Structure for CFc000105350 (3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid)

3D Structure for CFc000105350 (3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid)