Identification

PhytoHub ID
PHUB001594
Name
Caffeic acid 3'-sulfate
Systematic Name
4'-Hydroxycinnamic acid-3'-sulfate
Synonyms
Not Available
CAS Number
Not Available
Average Mass
260.22
Monoisotopic Mass
259.999073772
Chemical Formula
C9H8O7S
IUPAC Name
(2E)-3-[4-hydroxy-3-(sulfooxy)phenyl]prop-2-enoic acid
InChI Key
VWQNTRNACRFUCQ-DUXPYHPUSA-N
InChI Identifier
InChI=1S/C9H8O7S/c10-7-3-1-6(2-4-9(11)12)5-8(7)16-17(13,14)15/h1-5,10H,(H,11,12)(H,13,14,15)/b4-2+
SMILES
OC(=O)\C=C\C1=CC(OS(O)(=O)=O)=C(O)C=C1
Structure

Calculated Properties

Solubility (ALOGPS)
7.54e-01 g/l
LogS (ALOGPS)
-2.54
LogP (ALOGPS)
-0.37
Hydrogen Acceptors
6
Hydrogen Donors
3
Rotatable Bond Count
4
Polar Surface Area
121.13000000000001
Refractivity
57.0135
Polarizability
22.487222315069936
Formal Charge
0
Physiological Charge
-2
pKa (strongest basic)
-4.407550401842359
pKa (strongest acidic)
-2.3026952822384072
Number of Rings
1
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Metabolite

Family
(Poly)phenol metabolites
Class
Phenolic acid metabolites
Sub-class
Cinnamic acids

Taxonomy of its Food Phytochemical Precursor(s)

Food PhytochemicalFamilyClassSub-class
Caffeic acidPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
Orange flavanonesPolyphenolsFlavonoidsFlavanonesShow Food Phytochemical
Black tea Flavan-3-olsPolyphenolsFlavonoidsFlavan-3-olsShow Food Phytochemical
Coffee Chlorogenic acidsPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
Yerba mate Chlorogenic acidsPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
Grape (Poly)phenolsPolyphenolsNot specifiedNot specifiedShow Food Phytochemical
Globe artichoke (Poly)phenolsPolyphenolsNot specifiedNot specifiedShow Food Phytochemical
Red Raspberries AnthocyaninsPolyphenolsFlavonoidsAnthocyaninsShow Food Phytochemical
Coffee hydroxycinnamatesPolyphenolsFlavonoidsHydroxycinnamic acidsShow Food Phytochemical

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
Hydroxycinnamic acids
Alternative Parent Names
["1-hydroxy-2-unsubstituted benzenoids", "Carbonyl compounds", "Carboxylic acids", "Cinnamic acids", "Coumaric acids and derivatives", "Hydrocarbon derivatives", "Monocarboxylic acids and derivatives", "Organic oxides", "Phenoxy compounds", "Phenylsulfates", "Styrenes", "Sulfuric acid monoesters"]
External Descriptor Annotations
Not Available
Substituent Names
["1-hydroxy-2-unsubstituted benzenoid", "Aromatic homomonocyclic compound", "Arylsulfate", "Benzenoid", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Cinnamic acid", "Coumaric acid or derivatives", "Hydrocarbon derivative", "Hydroxycinnamic acid", "Monocarboxylic acid or derivatives", "Monocyclic benzene moiety", "Organic oxide", "Organic oxygen compound", "Organic sulfuric acid or derivatives", "Organooxygen compound", "Phenol", "Phenoxy compound", "Phenylsulfate", "Styrene", "Sulfate-ester", "Sulfuric acid ester", "Sulfuric acid monoester"]

Spectra from Online Resources

No spectra information available

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Caffeic acid Caffeic acid 3'-sulfatehumanplasmahost metabolismNot AvailableNot AvailableNot AvailableC9H8O7S259.999073772 Publications
Orange flavanones Caffeic acid 3'-sulfatehumanurinehost-gut microbiota co-metaboliteNot AvailableNot Available<1%C9H8O7S259.999073772 Detailed Intervention Studies Publications
Black tea Flavan-3-ols Caffeic acid 3'-sulfatehumanurinehost-gut microbiota co-metaboliteNot AvailableNot Available<1%C9H8O7S259.999073772 Detailed Intervention Studies Publications
Coffee Chlorogenic acids Caffeic acid 3'-sulfatehumanplasma, urinehost metabolism1h-3h50-200 nmol/L1-5%C9H8O7S259.999073772 Detailed Intervention Studies Publications
Yerba mate Chlorogenic acids Caffeic acid 3'-sulfatehumanplasma, urinehost metabolism<1h20-50 nmol/L<1%C9H8O7S259.999073772 Detailed Intervention Studies Publications
Grape (Poly)phenols Caffeic acid 3'-sulfatehumanplasma, urinehost metabolism1h-3h20-50 nmol/L<1%C9H8O7S259.999073772 Detailed Intervention Studies Publications
Globe artichoke (Poly)phenols Caffeic acid 3'-sulfatehumanplasma, urinehost metabolism1h-3h2-5┬Ámol/L<1%C9H8O7S259.999073772 Detailed Intervention Studies Publications
Red Raspberries Anthocyanins Caffeic acid 3'-sulfatehumanurinehost-gut microbiota co-metaboliteNot AvailableNot Available<1%C9H8O7S259.999073772 Detailed Intervention Studies Publications
Coffee hydroxycinnamates Caffeic acid 3'-sulfateNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC9H8O7S259.999073772 Detailed Intervention Studies

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
Coffee Chlorogenic acids Caffeic acid 3'-sulfateMicrobiotaEffect, clusters Publications
Globe artichoke (Poly)phenols Caffeic acid 3'-sulfateMicrobiotaEffect, clusters Publications
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