MiMeDB: Showing metabocard for Prephenate (MMDBc0029932)

Plant

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:47:19 UTC

Update Date

2022-08-31 17:37:42 UTC

Metabolite ID

MMDBc0029932

Metabolite Identification

Common Name

Prephenate

Description

Prephenic acid, more commonly known by its anionic form prephenate, is an intermediate in the biosynthesis of the aromatic amino acids phenylalanine and tyrosine.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305271900262D          

 16 16  0  0  0  0            999 V2000
   10.6660  -15.6362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9034  -16.3507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2535  -16.3507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4910  -17.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6660  -17.8902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4910  -15.6362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3806  -18.3026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0950  -17.8902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9515  -17.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6660  -17.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9034  -14.9216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3806  -19.1276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8090  -18.3026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0950  -17.0652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2370  -17.0652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9515  -18.3026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1  3  2  0  0  0  0
  2  4  2  0  0  0  0
  2  6  1  0  0  0  0
  3 10  1  0  0  0  0
  4 10  1  0  0  0  0
  5 10  1  0  0  0  0
  5  7  1  0  0  0  0
  6 11  1  0  0  0  0
  7 12  2  0  0  0  0
  7  8  1  0  0  0  0
  8 13  1  0  0  0  0
  8 14  2  0  0  0  0
  9 10  1  0  0  0  0
  9 15  1  0  0  0  0
  9 16  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029932

> <DATABASE_NAME>
MIME

> <SMILES>
OC1C=CC(CC(=O)C(O)=O)(C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O6/c11-6-1-3-10(4-2-6,9(15)16)5-7(12)8(13)14/h1-4,6,11H,5H2,(H,13,14)(H,15,16)

> <INCHI_KEY>
FPWMCUPFBRFMLH-UHFFFAOYSA-N

> <FORMULA>
C10H10O6

> <MOLECULAR_WEIGHT>
226.1828

> <EXACT_MASS>
226.047738052

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
19.72902046696766

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(2-carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid

> <ALOGPS_LOGP>
-0.31

> <JCHEM_LOGP>
0.06097045266666673

> <ALOGPS_LOGS>
-0.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.87542455823727

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.891510507673818

> <JCHEM_PKA_STRONGEST_BASIC>
-2.1244212194274477

> <JCHEM_POLAR_SURFACE_AREA>
111.9

> <JCHEM_REFRACTIVITY>
53.55400000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.60e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
prephenic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      19.910 -29.188   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.220 -30.521   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.140 -30.521   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.450 -31.855   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.910 -33.395   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.450 -29.188   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.244 -34.165   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.577 -33.395   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.576 -32.625   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.910 -31.855   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      22.220 -27.854   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      21.244 -35.705   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      23.910 -34.165   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      22.577 -31.855   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      17.242 -31.855   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      18.576 -34.165   0.000  0.00  0.00           O+0
CONECT    1    6    3                                                       
CONECT    2    4    6                                                       
CONECT    3    1   10                                                       
CONECT    4    2   10                                                       
CONECT    5   10    7                                                       
CONECT    6    1    2   11                                                  
CONECT    7    5   12    8                                                  
CONECT    8    7   13   14                                                  
CONECT    9   10   15   16                                                  
CONECT   10    3    4    5    9                                             
CONECT   11    6                                                            
CONECT   12    7                                                            
CONECT   13    8                                                            
CONECT   14    8                                                            
CONECT   15    9                                                            
CONECT   16    9                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

Synonyms

Value	Source
1-Carboxy-4-hydroxy-2,5-cyclohexadiene-1-pyruvic acid	ChEBI
1-Carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propanoic acid	ChEBI
1-Carboxy-4-hydroxy-2,5-cyclohexadiene-1-pyruvate	Generator
1-Carboxy-4-hydroxy-a-oxo-2,5-cyclohexadiene-1-propanoate	Generator
1-Carboxy-4-hydroxy-a-oxo-2,5-cyclohexadiene-1-propanoic acid	Generator
1-Carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propanoate	Generator
1-Carboxy-4-hydroxy-α-oxo-2,5-cyclohexadiene-1-propanoate	Generator
1-Carboxy-4-hydroxy-α-oxo-2,5-cyclohexadiene-1-propanoic acid	Generator
Prephenic acid	Generator
PRE	HMDB

Molecular Formula

C₁₀H₁₀O₆

Average Mass

226.1828

Monoisotopic Mass

226.047738052

IUPAC Name

1-(2-carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid

Traditional Name

prephenic acid

CAS Registry Number

126-49-8

SMILES

OC1C=CC(CC(=O)C(O)=O)(C=C1)C(O)=O

InChI Identifier

InChI=1S/C10H10O6/c11-6-1-3-10(4-2-6,9(15)16)5-7(12)8(13)14/h1-4,6,11H,5H2,(H,13,14)(H,15,16)

InChI Key

FPWMCUPFBRFMLH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Gamma-keto acids and derivatives

Direct Parent

Gamma-keto acids and derivatives

Alternative Parents

Substituents

Gamma-keto acid
Dicarboxylic acid or derivatives
Alpha-keto acid
Alpha-hydroxy ketone
Secondary alcohol
Ketone
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

oxo dicarboxylic acid (CHEBI:16666 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	36 g/L	ALOGPS
logP	-0.31	ALOGPS
logP	0.061	ChemAxon
logS	-0.8	ALOGPS
pKa (Strongest Acidic)	2.89	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	53.55 m³·mol⁻¹	ChemAxon
Polarizability	19.73 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

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated 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	346	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; Cattle ; River trout ; Lion ; Chicken	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	364	Human feces; Human pleural fluid plaque; Pig ; Human ; Cattle	Metabolic reconstruction
Bacteria	Actinobacteria	139	Human feces; Human pleural fluid plaque; Human dental plaque; Human ; Human sputum; Human nasopharyngeal swab; Cattle	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	109	Human feces; Human appendix biopsy; Human	Metabolic reconstruction
Bacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1	Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	19	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5	Human feces; Cattle ; Human	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1	Human feces	Metabolic reconstruction
Bacteria	Deinococcus-Thermus	3
Eukaryota/Fungi	Ascomycota	7	Human feces	Unknown
Archaea/Archaea	Euryarchaeota	1	Human feces; Cattle ; Human	Metabolic reconstruction
Bacteria	Aquificae	1
Eukaryota/Fungi	Basidiomycota	1
Bacteria	Chlorobi	1
nah	1
Bacteria	Cyanobacteria	1
Bacteria/NULL	Proteobacteria	1	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; Cattle ; River trout ; Lion ; Chicken	Unknown; Metabolic reconstruction

Exposure Sources

Food Exposures

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

HMDB0012283

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Prephenic_acid

METLIN ID

Not Available

PubChem Compound

1028

PDB ID

Not Available

ChEBI ID

16666

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

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 ]
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 Prephenate (MMDBc0029932)

MOL for #<Metabolite:0x00007f12182df100>

3D MOL for #<Metabolite:0x00007f12182df100>

3D SDF for #<Metabolite:0x00007f12182df100>

3D-SDF for #<Metabolite:0x00007f12182df100>

PDB for #<Metabolite:0x00007f12182df100>

3D PDB for #<Metabolite:0x00007f12182df100>

SMILES for #<Metabolite:0x00007f12182df100>

INCHI for #<Metabolite:0x00007f12182df100>

Structure for #<Metabolite:0x00007f12182df100>

3D Structure for #<Metabolite:0x00007f12182df100>