MiMeDB: Showing metabocard for (E)-caffeate (MMDBc0055015)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:39:53 UTC

Update Date

2022-08-12 20:09:11 UTC

Metabolite ID

MMDBc0055015

Metabolite Identification

Common Name

(E)-caffeate

Description

trans-caffeate, also known as (e)-caffeate or (e)-caffeic acid, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. trans-caffeate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on trans-caffeate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221392D          

 15 15  0  0  0  0            999 V2000
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  8  5  1  0  0  0  0
  8  7  2  0  0  0  0
  9  4  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  2  0  0  0  0
 13  9  1  0  0  0  0
 14  2  1  0  0  0  0
 15  4  1  0  0  0  0
M  CHG  1  10  -1
M  END
> <DATABASE_ID>
MMDBc0055015

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(=C(\[H])C1=CC(O)=C([O-])C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/p-1/b4-2+

> <INCHI_KEY>
QAIPRVGONGVQAS-DUXPYHPUSA-M

> <FORMULA>
C9H7O4

> <MOLECULAR_WEIGHT>
179.152

> <EXACT_MASS>
179.034982285

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
16.943542519756335

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(1E)-2-carboxyeth-1-en-1-yl]-2-hydroxybenzen-1-olate

> <JCHEM_LOGP>
1.5289556166666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.276437669500657

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6438401388538604

> <JCHEM_PKA_STRONGEST_BASIC>
-6.283746523508147

> <JCHEM_POLAR_SURFACE_AREA>
80.59

> <JCHEM_REFRACTIVITY>
57.571999999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-[(1E)-2-carboxyeth-1-en-1-yl]-2-hydroxybenzenolate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O-1
HETATM   11  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   14  H   UNK     0       2.667  -3.080   0.000  0.00  0.00           H+0
HETATM   15  H   UNK     0      -1.334  -2.310   0.000  0.00  0.00           H+0
CONECT    1    3    6                                                       
CONECT    2    4    6   14                                                  
CONECT    3    1    7                                                       
CONECT    4    2    9   15                                                  
CONECT    5    6    8                                                       
CONECT    6    1    2    5                                                  
CONECT    7    3    8   10                                                  
CONECT    8    5    7   11                                                  
CONECT    9    4   12   13                                                  
CONECT   10    7                                                            
CONECT   11    8                                                            
CONECT   12    9                                                            
CONECT   13    9                                                            
CONECT   14    2                                                            
CONECT   15    4                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

Synonyms

Value	Source
(2E)-3-(3,4-Dihydroxyphenyl)acrylate	ChEBI
(e)-Caffeate	ChEBI
3,4-Dihydroxy-trans-cinnamate	ChEBI
trans-Caffeate anion	ChEBI
trans-Caffeate(1-)	ChEBI
(2E)-3-(3,4-Dihydroxyphenyl)acrylic acid	Generator
(e)-Caffeic acid	Generator
3,4-Dihydroxy-trans-cinnamic acid	Generator
trans-Caffeic acid anion	Generator
trans-Caffeic acid(1-)	Generator
trans-Caffeic acid	Generator

Molecular Formula

C₉H₇O₄

Average Mass

179.152

Monoisotopic Mass

179.034982285

IUPAC Name

4-[(1E)-2-carboxyeth-1-en-1-yl]-2-hydroxybenzen-1-olate

Traditional Name

4-[(1E)-2-carboxyeth-1-en-1-yl]-2-hydroxybenzenolate

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])C1=CC(O)=C([O-])C=C1)C(O)=O

InChI Identifier

InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/p-1/b4-2+

InChI Key

QAIPRVGONGVQAS-DUXPYHPUSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids

Alternative Parents

Substituents

Cinnamic acid
Coumaric acid or derivatives
Hydroxycinnamic acid
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Phenoxide
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carboxylic acid
Carbonyl group
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organic anion
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

hydroxy monocarboxylic acid anion (CHEBI:57770 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	1.53	ChemAxon
pKa (Strongest Acidic)	3.64	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	80.59 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	57.57 m³·mol⁻¹	ChemAxon
Polarizability	16.94 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites
Eukaryota/Fungi	Ascomycota	1	Human feces
Eukaryota/Fungi	Basidiomycota	1	Human feces
Bacteria	Firmicutes	1

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00004184

Chemspider ID

4450294

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Caffeic acid

METLIN ID

Not Available

PubChem Compound

5288055

PDB ID

Not Available

ChEBI ID

57770

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for (E)-caffeate (MMDBc0055015)

MOL for #<Metabolite:0x00007fdb4400c068>

3D MOL for #<Metabolite:0x00007fdb4400c068>

3D SDF for #<Metabolite:0x00007fdb4400c068>

3D-SDF for #<Metabolite:0x00007fdb4400c068>

PDB for #<Metabolite:0x00007fdb4400c068>

3D PDB for #<Metabolite:0x00007fdb4400c068>

SMILES for #<Metabolite:0x00007fdb4400c068>

INCHI for #<Metabolite:0x00007fdb4400c068>

Structure for #<Metabolite:0x00007fdb4400c068>

3D Structure for #<Metabolite:0x00007fdb4400c068>