MiMeDB: Showing metabocard for 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate (MMDBc0029981)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:49:18 UTC

Update Date

2022-08-31 17:38:18 UTC

Metabolite ID

MMDBc0029981

Metabolite Identification

Common Name

2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate

Description

2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate is a member of the chemical class known as Tricarboxylic Acids and Derivatives. These are organic compounds containing three carboxylic acid groups (or salt/ester derivatives thereof).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 08131209232D          

 27 27  0  0  0  0            999 V2000
    2.1434    5.3625    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    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    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
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  2  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
    2.1434    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    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
    1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 O   0  0  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
    2.8579    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  1  2  0  0  0  0
  7  2  1  0  0  0  0
  8  3  1  0  0  0  0
  7  8  1  6  0  0  0
  9  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  7  1  0  0  0  0
 12  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13  6  1  0  0  0  0
 11 14  1  1  0  0  0
 15  8  2  0  0  0  0
 16 10  2  0  0  0  0
 17 10  1  0  0  0  0
 12 18  1  6  0  0  0
 19 13  2  0  0  0  0
 20 13  1  0  0  0  0
 21 14  2  0  0  0  0
 22 14  1  0  0  0  0
 23  6  1  0  0  0  0
  9 23  1  1  0  0  0
  7 24  1  1  0  0  0
  9 25  1  6  0  0  0
 11 26  1  6  0  0  0
 12 27  1  1  0  0  0
M  END


  Mrv0541 08131209232D          

 27 27  0  0  0  0            999 V2000
    2.1434    5.3625    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    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    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
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  2  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
    2.1434    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    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
    1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 O   0  0  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
    2.8579    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  1  2  0  0  0  0
  7  2  1  0  0  0  0
  8  3  1  0  0  0  0
  7  8  1  6  0  0  0
  9  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  7  1  0  0  0  0
 12  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13  6  1  0  0  0  0
 11 14  1  1  0  0  0
 15  8  2  0  0  0  0
 16 10  2  0  0  0  0
 17 10  1  0  0  0  0
 12 18  1  6  0  0  0
 19 13  2  0  0  0  0
 20 13  1  0  0  0  0
 21 14  2  0  0  0  0
 22 14  1  0  0  0  0
 23  6  1  0  0  0  0
  9 23  1  1  0  0  0
  7 24  1  1  0  0  0
  9 25  1  6  0  0  0
 11 26  1  6  0  0  0
 12 27  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029981

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(O)[C@@]([H])(OC(=C)C(O)=O)C=C[C@]([H])(C(=O)CCC(O)=O)[C@@]1([H])C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O9/c1-6(13(19)20)23-9-4-2-7(8(15)3-5-10(16)17)11(12(9)18)14(21)22/h2,4,7,9,11-12,18H,1,3,5H2,(H,16,17)(H,19,20)(H,21,22)/t7-,9+,11-,12-/m1/s1

> <INCHI_KEY>
XYCATPIYKOARSZ-OAIFWDMCSA-N

> <FORMULA>
C14H16O9

> <MOLECULAR_WEIGHT>
328.2714

> <EXACT_MASS>
328.07943211

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
29.903126791278343

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,5S,6S)-5-[(1-carboxyeth-1-en-1-yl)oxy]-2-(3-carboxypropanoyl)-6-hydroxycyclohex-3-ene-1-carboxylic acid

> <ALOGPS_LOGP>
0.24

> <JCHEM_LOGP>
-0.5986455150000004

> <ALOGPS_LOGS>
-1.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.760286904779312

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.188935401161892

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4197602293226232

> <JCHEM_POLAR_SURFACE_AREA>
158.43

> <JCHEM_REFRACTIVITY>
74.11850000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.52e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sephchc

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-AUG-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-AUG-12         0                                  
HETATM    1  C   UNK     0       0.000   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   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       0.000   0.000   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   24  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2    4    7                                                       
CONECT    3    5    8                                                       
CONECT    4    2    9                                                       
CONECT    5    3   10                                                       
CONECT    6    1   13   23                                                  
CONECT    7    2    8   11   24                                             
CONECT    8    3    7   15                                                  
CONECT    9    4   12   23   25                                             
CONECT   10    5   16   17                                                  
CONECT   11    7   12   14   26                                             
CONECT   12    9   11   18   27                                             
CONECT   13    6   19   20                                                  
CONECT   14   11   21   22                                                  
CONECT   15    8                                                            
CONECT   16   10                                                            
CONECT   17   10                                                            
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20   13                                                            
CONECT   21   14                                                            
CONECT   22   14                                                            
CONECT   23    6    9                                                       
CONECT   24    7                                                            
CONECT   25    9                                                            
CONECT   26   11                                                            
CONECT   27   12                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   54    0
END

Synonyms

Value	Source
2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylic acid	ChEBI
5-Enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylic acid	ChEBI
5-Enolpyruvoyl-6-hydroxy-2-succinylcyclohex-3-ene-1-carboxylate	ChEBI
SEPHCHC	ChEBI
5-Enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate	Generator
5-Enolpyruvoyl-6-hydroxy-2-succinylcyclohex-3-ene-1-carboxylic acid	Generator
SEPHCHC CPD	MeSH

Molecular Formula

C₁₄H₁₆O₉

Average Mass

328.2714

Monoisotopic Mass

328.07943211

IUPAC Name

(1R,2S,5S,6S)-5-[(1-carboxyeth-1-en-1-yl)oxy]-2-(3-carboxypropanoyl)-6-hydroxycyclohex-3-ene-1-carboxylic acid

Traditional Name

sephchc

CAS Registry Number

Not Available

SMILES

[H][C@@]1(O)[C@@]([H])(OC(=C)C(O)=O)C=C[C@]([H])(C(=O)CCC(O)=O)[C@@]1([H])C(O)=O

InChI Identifier

InChI=1S/C14H16O9/c1-6(13(19)20)23-9-4-2-7(8(15)3-5-10(16)17)11(12(9)18)14(21)22/h2,4,7,9,11-12,18H,1,3,5H2,(H,16,17)(H,19,20)(H,21,22)/t7-,9+,11-,12-/m1/s1

InChI Key

XYCATPIYKOARSZ-OAIFWDMCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Gamma-keto acid
Beta-hydroxy acid
Keto acid
Hydroxy acid
Secondary alcohol
Ketone
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

tricarboxylic acid (CHEBI:50271 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	4.52 g/L	ALOGPS
logP	0.24	ALOGPS
logP	-0.6	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	3.19	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	158.43 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	74.12 m³·mol⁻¹	ChemAxon
Polarizability	29.9 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

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
MMDBr0018884	Oxoglutaric acid	2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate	2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase	Synthesis	PathBank	31602464
MMDBr0018886	2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate	(1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate	2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase	Synthesis	PathBank	31602464

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	6	Pig ; Human feces; Human ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; Human stool	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	73	Pig ; Human feces; Human ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; Human stool	Unknown; Metabolic reconstruction
Bacteria	Actinobacteria	12	Human feces; Human pleural fluid plaque; Human dental plaque; Human sputum; Human ; Human nasopharyngeal swab; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	63	Human feces; Human pleural fluid plaque; Human dental plaque; Human sputum; Human ; Human nasopharyngeal swab; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	95	Human feces; Human ; Human subgingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	101	Human feces; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria	Firmicutes	7	Human feces; Human ; Human subgingival plaque	Metabolic reconstruction
Archaea	Euryarchaeota	1		Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

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

Not Available

KEGG Compound ID

C16519

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24883454

PDB ID

Not Available

ChEBI ID

50271

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate (MMDBc0029981)

MOL for #<Metabolite:0x00005645c9c19f70>

3D MOL for #<Metabolite:0x00005645c9c19f70>

3D SDF for #<Metabolite:0x00005645c9c19f70>

3D-SDF for #<Metabolite:0x00005645c9c19f70>

PDB for #<Metabolite:0x00005645c9c19f70>

3D PDB for #<Metabolite:0x00005645c9c19f70>

SMILES for #<Metabolite:0x00005645c9c19f70>

INCHI for #<Metabolite:0x00005645c9c19f70>

Structure for #<Metabolite:0x00005645c9c19f70>

3D Structure for #<Metabolite:0x00005645c9c19f70>