MiMeDB: Showing metabocard for 2-Hydroxy-6-ketononadienedicarboxylate (MMDBc0029784)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:41:30 UTC

Update Date

2022-08-31 17:16:55 UTC

Metabolite ID

MMDBc0029784

Metabolite Identification

Common Name

2-Hydroxy-6-ketononadienedicarboxylate

Description

2-hydroxy-6-ketononadienedicarboxylate is an intermediate in phenylalanine metabolism. It is converted from 2,3-dihydroxy-phenylpropanoate by 2,3-dihydroxyphenylpropionate 1,2-dioxygenase (EC:1.13.11.-), and form succinate and cis-2-hydroxypenta-2,4-dienoate by 2-hydroxy-6-ketonona-2,4-dienedioic acid hydrolase (EC:3.7.1.-) (KEGG)

Structure

MOL SDF PDB SMILES InChI


  Mrv1533005141512452D          

 15 14  0  0  0  0            999 V2000
   -6.1607   -0.5357    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -5.4462   -0.1232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7317   -0.5357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0173   -0.1232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3028   -0.5357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5883   -0.1232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8738   -0.5357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1594   -0.1232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4449   -0.5357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2695   -0.1232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9839   -0.5357    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -5.4462    0.7017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7317   -1.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8738   -1.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2695    0.7017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 15  2  0  0  0  0
 10 11  1  0  0  0  0
  7 14  2  0  0  0  0
  3 13  1  0  0  0  0
  1  2  1  0  0  0  0
  2 12  2  0  0  0  0
M  CHG  2   1  -1  11  -1
M  END
> <DATABASE_ID>
MMDBc0029784

> <DATABASE_NAME>
MIME

> <SMILES>
O\C(=C/C=C/C(=O)CCC([O-])=O)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O6/c10-6(4-5-8(12)13)2-1-3-7(11)9(14)15/h1-3,11H,4-5H2,(H,12,13)(H,14,15)/p-2/b2-1+,7-3-

> <INCHI_KEY>
RFENOVFRMPRRJI-YDCWOTKKSA-L

> <FORMULA>
C9H8O6

> <MOLECULAR_WEIGHT>
212.158

> <EXACT_MASS>
212.033185137

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
19.10419130602064

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z,4E)-2-hydroxy-6-oxonona-2,4-dienedioate

> <ALOGPS_LOGP>
0.40

> <JCHEM_LOGP>
0.12213193033333311

> <ALOGPS_LOGS>
-1.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.183327830152915

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2502389629001076

> <JCHEM_PKA_STRONGEST_BASIC>
-5.407026912458795

> <JCHEM_POLAR_SURFACE_AREA>
117.55999999999999

> <JCHEM_REFRACTIVITY>
73.0116

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.27e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,4E)-2-hydroxy-6-oxonona-2,4-dienedioate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAY-15         0                                  
HETATM    1  O   UNK     0     -11.500  -1.000   0.000  0.00  0.00           O-1
HETATM    2  C   UNK     0     -10.166  -0.230   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.833  -1.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.499  -0.230   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.165  -1.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.831  -0.230   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.498  -1.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.164  -0.230   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.830  -1.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.503  -0.230   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.837  -1.000   0.000  0.00  0.00           O-1
HETATM   12  O   UNK     0     -10.166   1.310   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -8.833  -2.540   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -3.498  -2.540   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.503   1.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    3    1   12                                                  
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   15   11                                                  
CONECT   11   10                                                            
CONECT   12    2                                                            
CONECT   13    3                                                            
CONECT   14    7                                                            
CONECT   15   10                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

Synonyms

Value	Source
(2Z,4E)-2-Hydroxy-6-oxonona-2,4-dienedioate	ChEBI
(2Z,4E)-2-Hydroxy-6-oxonona-2,4-dienedioic acid	Generator
2-Hydroxy-6-ketononadienedicarboxylic acid	Generator
(2Z,4E)-2-Hydroxy-6-oxonona-2,4-diene-1,9-dioic acid	Generator

Molecular Formula

C₉H₈O₆

Average Mass

212.158

Monoisotopic Mass

212.033185137

IUPAC Name

(2Z,4E)-2-hydroxy-6-oxonona-2,4-dienedioate

Traditional Name

(2Z,4E)-2-hydroxy-6-oxonona-2,4-dienedioate

CAS Registry Number

53-42-9

SMILES

O\C(=C/C=C/C(=O)CCC([O-])=O)C([O-])=O

InChI Identifier

InChI=1S/C9H10O6/c10-6(4-5-8(12)13)2-1-3-7(11)9(14)15/h1-3,11H,4-5H2,(H,12,13)(H,14,15)/p-2/b2-1+,7-3-

InChI Key

RFENOVFRMPRRJI-YDCWOTKKSA-L

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Medium-chain keto acids and derivatives

Direct Parent

Medium-chain keto acids and derivatives

Alternative Parents

Substituents

Medium-chain keto acid
Gamma-keto acid
Dicarboxylic acid or derivatives
Fatty acyl
Unsaturated fatty acid
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Ketone
Carboxylic acid derivative
Carboxylic acid
Enolate
Carbonyl group
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-hydroxy-6-oxonona-2,4-dienedioate (CHEBI:66887 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	7.27 g/L	ALOGPS
logP	0.4	ALOGPS
logP	0.12	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	3.25	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	117.56 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	73.01 m³·mol⁻¹	ChemAxon
Polarizability	19.1 Å³	ChemAxon
Number of Rings	0	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	Microbial Links
Bacteria	Proteobacteria	29	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Human supragingival plaque	Unknown
Bacteria	Actinobacteria	12	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21158453

PDB ID

Not Available

ChEBI ID

66887

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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 ]
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 2-Hydroxy-6-ketononadienedicarboxylate (MMDBc0029784)

MOL for #<Metabolite:0x00007fed14174f18>

3D MOL for #<Metabolite:0x00007fed14174f18>

3D SDF for #<Metabolite:0x00007fed14174f18>

3D-SDF for #<Metabolite:0x00007fed14174f18>

PDB for #<Metabolite:0x00007fed14174f18>

3D PDB for #<Metabolite:0x00007fed14174f18>

SMILES for #<Metabolite:0x00007fed14174f18>

INCHI for #<Metabolite:0x00007fed14174f18>

Structure for #<Metabolite:0x00007fed14174f18>

3D Structure for #<Metabolite:0x00007fed14174f18>