MiMeDB: Showing metabocard for 3-[(1E,4R)-4-hydroxycyclohex-2-en-1-ylidene]pyruvic acid (MMDBc0055334)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:49:29 UTC

Update Date

2022-08-12 20:09:20 UTC

Metabolite ID

MMDBc0055334

Metabolite Identification

Common Name

3-[(1E,4R)-4-hydroxycyclohex-2-en-1-ylidene]pyruvic acid

Description

3-[(1E,4R)-4-hydroxycyclohex-2-en-1-ylidene]pyruvate belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon. 3-[(1E,4R)-4-hydroxycyclohex-2-en-1-ylidene]pyruvate 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 3-[(1E,4R)-4-hydroxycyclohex-2-en-1-ylidene]pyruvate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221492D          

 15 15  0  0  1  0            999 V2000
    1.4289   -0.0000    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    0.8250    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   -1.2375    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  1  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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    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
    1.4289    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  1  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
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  8  1  0  0  0  0
  7 10  1  1  0  0  0
 11  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13  9  2  0  0  0  0
 14  5  1  0  0  0  0
  7 15  1  6  0  0  0
M  CHG  1  12  -1
M  END
> <DATABASE_ID>
MMDBc0055334

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1,3,5,7,10H,2,4H2,(H,12,13)/p-1/b6-5-/t7-/m0/s1

> <INCHI_KEY>
MPMDLNLJFJLITQ-RBSILHGTSA-M

> <FORMULA>
C9H9O4

> <MOLECULAR_WEIGHT>
181.168

> <EXACT_MASS>
181.05063235

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
17.157213787351985

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(1E,4R)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate

> <JCHEM_LOGP>
0.7294105953333331

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.43110891365826

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.225597038707334

> <JCHEM_PKA_STRONGEST_BASIC>
-1.7354383897818906

> <JCHEM_POLAR_SURFACE_AREA>
77.43

> <JCHEM_REFRACTIVITY>
58.062900000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-[(1E,4R)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate

> <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       0.000  -0.000   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   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   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  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O-1
HETATM   13  O   UNK     0      -1.334  -0.770   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       2.667   3.080   0.000  0.00  0.00           H+0
CONECT    1    3    6                                                       
CONECT    2    4    6                                                       
CONECT    3    1    7                                                       
CONECT    4    2    7                                                       
CONECT    5    6    8   14                                                  
CONECT    6    1    2    5                                                  
CONECT    7    3    4   10   15                                             
CONECT    8    5    9   11                                                  
CONECT    9    8   12   13                                                  
CONECT   10    7                                                            
CONECT   11    8                                                            
CONECT   12    9                                                            
CONECT   13    9                                                            
CONECT   14    5                                                            
CONECT   15    7                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

Synonyms

Value	Source
3-[(1E,4R)-4-Hydroxycyclohex-2-en-1-ylidene]pyruvic acid	Generator

Molecular Formula

C₉H₉O₄

Average Mass

181.168

Monoisotopic Mass

181.05063235

IUPAC Name

3-[(1E,4R)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate

Traditional Name

3-[(1E,4R)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C9H10O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1,3,5,7,10H,2,4H2,(H,12,13)/p-1/b6-5-/t7-/m0/s1

InChI Key

MPMDLNLJFJLITQ-RBSILHGTSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Alpha-keto acids and derivatives

Direct Parent

Alpha-keto acids and derivatives

Alternative Parents

Substituents

Alpha-keto acid
Acryloyl-group
Enone
Secondary alcohol
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic anion
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

3-(4-hydroxycyclohex-2-en-1-ylidene)pyruvate (CHEBI:84355 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	0.73	ChemAxon
pKa (Strongest Acidic)	3.23	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	77.43 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	58.06 m³·mol⁻¹	ChemAxon
Polarizability	17.16 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	Firmicutes	3	Human ; Human feces

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

Not Available

Chemspider ID

34999429

KEGG Compound ID

Not Available

BioCyc ID

CPD-17511

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

86583389

PDB ID

Not Available

ChEBI ID

84355

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 3-[(1E,4R)-4-hydroxycyclohex-2-en-1-ylidene]pyruvic acid (MMDBc0055334)

MOL for #<Metabolite:0x00007fdb50865780>

3D MOL for #<Metabolite:0x00007fdb50865780>

3D SDF for #<Metabolite:0x00007fdb50865780>

3D-SDF for #<Metabolite:0x00007fdb50865780>

PDB for #<Metabolite:0x00007fdb50865780>

3D PDB for #<Metabolite:0x00007fdb50865780>

SMILES for #<Metabolite:0x00007fdb50865780>

INCHI for #<Metabolite:0x00007fdb50865780>

Structure for #<Metabolite:0x00007fdb50865780>

3D Structure for #<Metabolite:0x00007fdb50865780>