MiMeDB: Showing metabocard for (2E)-3-(2,3-dihydroxyphenyl)prop-2-enoic acid (MMDBc0054804)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:35:12 UTC

Update Date

2022-08-12 20:09:05 UTC

Metabolite ID

MMDBc0054804

Metabolite Identification

Common Name

(2E)-3-(2,3-dihydroxyphenyl)prop-2-enoic acid

Description

2,3-dihydroxy-trans-cinnamate 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. Based on a literature review very few articles have been published on 2,3-dihydroxy-trans-cinnamate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221352D          

 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
    1.4289    0.8250    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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    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   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    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
   -0.7145   -0.4125    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  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
   -0.0000    2.4750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  6  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  3  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  2  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14  4  1  0  0  0  0
 15  5  1  0  0  0  0
M  CHG  1  10  -1
M  END
> <DATABASE_ID>
MMDBc0054804

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O4/c10-7-3-1-2-6(9(7)13)4-5-8(11)12/h1-5,10,13H,(H,11,12)/p-1/b5-4+

> <INCHI_KEY>
SIUKXCMDYPYCLH-SNAWJCMRSA-M

> <FORMULA>
C9H7O4

> <MOLECULAR_WEIGHT>
179.152

> <EXACT_MASS>
179.034982285

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
16.826171884165234

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(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>
9.256929884535694

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6744605168479487

> <JCHEM_PKA_STRONGEST_BASIC>
-6.301002878847684

> <JCHEM_POLAR_SURFACE_AREA>
80.59

> <JCHEM_REFRACTIVITY>
57.572

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-[(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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O-1
HETATM   11  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   14  H   UNK     0      -0.000   4.620   0.000  0.00  0.00           H+0
HETATM   15  H   UNK     0       4.001   3.850   0.000  0.00  0.00           H+0
CONECT    1    2    3                                                       
CONECT    2    1    6                                                       
CONECT    3    1    7                                                       
CONECT    4    5    6   14                                                  
CONECT    5    4    8   15                                                  
CONECT    6    2    4    9                                                  
CONECT    7    3    9   10                                                  
CONECT    8    5   11   12                                                  
CONECT    9    6    7   13                                                  
CONECT   10    7                                                            
CONECT   11    8                                                            
CONECT   12    8                                                            
CONECT   13    9                                                            
CONECT   14    4                                                            
CONECT   15    5                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

Synonyms

Value	Source
(2E)-3-(2,3-Dihydroxyphenyl)prop-2-enoate	ChEBI
(2E)-3-(2,3-Dihydroxyphenyl)prop-2-enoic acid	Generator
2,3-Dihydroxy-trans-cinnamic acid	Generator

Molecular Formula

C₉H₇O₄

Average Mass

179.152

Monoisotopic Mass

179.034982285

IUPAC Name

3-[(1E)-2-carboxyeth-1-en-1-yl]-2-hydroxybenzen-1-olate

Traditional Name

3-[(1E)-2-carboxyeth-1-en-1-yl]-2-hydroxybenzenolate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C9H8O4/c10-7-3-1-2-6(9(7)13)4-5-8(11)12/h1-5,10,13H,(H,11,12)/p-1/b5-4+

InChI Key

SIUKXCMDYPYCLH-SNAWJCMRSA-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

cinnamates (CHEBI:58642 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	1.53	ChemAxon
pKa (Strongest Acidic)	3.67	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	16.83 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

Not Available

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	Microbial Links
Bacteria	Proteobacteria	36	Human ; Human supragingival plaque; Human feces; Human feces; pleural fluid plaque; bal; Human stool
Bacteria	Actinobacteria	13	Cattle ; Human

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

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

Not Available

Chemspider ID

20118162

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21158539

PDB ID

Not Available

ChEBI ID

58642

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 (2E)-3-(2,3-dihydroxyphenyl)prop-2-enoic acid (MMDBc0054804)

MOL for #<Metabolite:0x00007fecb71b8db0>

3D MOL for #<Metabolite:0x00007fecb71b8db0>

3D SDF for #<Metabolite:0x00007fecb71b8db0>

3D-SDF for #<Metabolite:0x00007fecb71b8db0>

PDB for #<Metabolite:0x00007fecb71b8db0>

3D PDB for #<Metabolite:0x00007fecb71b8db0>

SMILES for #<Metabolite:0x00007fecb71b8db0>

INCHI for #<Metabolite:0x00007fecb71b8db0>

Structure for #<Metabolite:0x00007fecb71b8db0>

3D Structure for #<Metabolite:0x00007fecb71b8db0>