MiMeDB: Showing metabocard for Chorismate (MMDBc0029921)

Plant

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:46:54 UTC

Update Date

2022-08-31 17:37:38 UTC

Metabolite ID

MMDBc0029921

Metabolite Identification

Common Name

Chorismate

Description

Chorismic acid, more commonly known as its anionic form chorismate, is an important biochemical intermediate in plants and microorganisms. It is a precursor for the aromatic amino acids phenylalanine and tyrosine,indole, indole derivatives and tryptophan,2,3-dihydroxybenzoic acid (DHB) used for enterobactin biosynthesis,the plant hormone salicylic acid and many alkaloids and other aromatic metabolites. -- Wikipedia

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652309042000342D          

 16 16  0  0  0  0            999 V2000
 9999.279610000.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5651 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.850610000.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5651 9999.1760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1362 9999.9999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.850610001.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2796 9998.7624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.140110000.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8537 9999.9999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.140110001.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.709710000.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.995210000.0003    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.9952 9999.1752    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.7097 9998.7628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4242 9999.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.424210000.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  3  5  1  0  0  0  0
  3  6  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 11 12  1  0  0  0  0
 11 16  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 12  1  1  6  0  0  0
 13  7  1  1  0  0  0
 16  8  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029921

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O6/c1-5(9(12)13)16-8-4-6(10(14)15)2-3-7(8)11/h2-4,7-8,11H,1H2,(H,12,13)(H,14,15)/t7-,8-/m1/s1

> <INCHI_KEY>
WTFXTQVDAKGDEY-HTQZYQBOSA-N

> <FORMULA>
C10H10O6

> <MOLECULAR_WEIGHT>
226.1828

> <EXACT_MASS>
226.047738052

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
20.487779256263384

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4R)-3-[(1-carboxyeth-1-en-1-yl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid

> <ALOGPS_LOGP>
0.52

> <JCHEM_LOGP>
-0.12549059733333331

> <ALOGPS_LOGS>
-1.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.206666263255496

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3942809060486976

> <JCHEM_PKA_STRONGEST_BASIC>
-3.356475185932375

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
54.310100000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.80e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chorismic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  O   UNK     0    8665.3228667.437   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8663.9888666.666   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8662.6548667.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8663.9888665.129   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8661.3218666.666   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8662.6548668.977   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8665.3228664.356   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8670.6628667.437   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8671.9948666.666   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8670.6628668.977   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8667.9918667.437   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8666.6588666.667   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8666.6588665.127   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8667.9918664.357   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8669.3258665.127   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8669.3258666.667   0.000  0.00  0.00           C+0
CONECT    1    2   12                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2    5    6                                                  
CONECT    4    2                                                            
CONECT    5    3                                                            
CONECT    6    3                                                            
CONECT    7   13                                                            
CONECT    8    9   10   16                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11   12   16                                                       
CONECT   12   11   13    1                                                  
CONECT   13   12   14    7                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   11   15    8                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0012199
HETATM    1  C1  UNL     1       1.688   2.245   0.753  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.129   1.052   0.427  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.319  -0.029   0.571  1.00  0.00           O  
HETATM    4  C3  UNL     1       0.390  -0.486  -0.414  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.608   0.506  -0.746  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.904   0.290  -0.669  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.862   1.352  -1.025  1.00  0.00           C  
HETATM    8  O2  UNL     1      -2.469   2.483  -1.408  1.00  0.00           O  
HETATM    9  O3  UNL     1      -4.227   1.133  -0.946  1.00  0.00           O  
HETATM   10  C7  UNL     1      -2.436  -0.991  -0.226  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.592  -1.929   0.096  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.149  -1.782   0.045  1.00  0.00           C  
HETATM   13  O4  UNL     1       0.415  -2.856  -0.717  1.00  0.00           O  
HETATM   14  C10 UNL     1       3.471   0.874  -0.088  1.00  0.00           C  
HETATM   15  O5  UNL     1       4.278   1.852  -0.245  1.00  0.00           O  
HETATM   16  O6  UNL     1       3.973  -0.371  -0.443  1.00  0.00           O  
HETATM   17  H1  UNL     1       0.694   2.429   1.141  1.00  0.00           H  
HETATM   18  H2  UNL     1       2.356   3.088   0.627  1.00  0.00           H  
HETATM   19  H3  UNL     1       0.961  -0.692  -1.375  1.00  0.00           H  
HETATM   20  H4  UNL     1      -0.292   1.490  -1.078  1.00  0.00           H  
HETATM   21  H5  UNL     1      -4.665   0.578  -0.213  1.00  0.00           H  
HETATM   22  H6  UNL     1      -3.516  -1.170  -0.164  1.00  0.00           H  
HETATM   23  H7  UNL     1      -2.031  -2.903   0.432  1.00  0.00           H  
HETATM   24  H8  UNL     1       0.261  -1.972   1.093  1.00  0.00           H  
HETATM   25  H9  UNL     1       1.346  -2.950  -0.422  1.00  0.00           H  
HETATM   26  H10 UNL     1       3.470  -1.240  -0.291  1.00  0.00           H  
CONECT    1    2    2   17   18
CONECT    2    3   14
CONECT    3    4
CONECT    4    5   12   19
CONECT    5    6    6   20
CONECT    6    7   10
CONECT    7    8    8    9
CONECT    9   21
CONECT   10   11   11   22
CONECT   11   12   23
CONECT   12   13   24
CONECT   13   25
CONECT   14   15   15   16
CONECT   16   26
END

Synonyms

Value	Source
(3R,4R)-3-[(1-Carboxyvinyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid	ChEBI
(3R-trans)-3-((1-Carboxyethenyl)oxy)-4-hydroxy-1,5-cyclohexadiene-1-carboxylic acid	ChEBI
Chorismic acid	Kegg
(3R,4R)-3-[(1-Carboxyethenyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylate	Kegg
(3R,4R)-3-[(1-Carboxyvinyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylate	Generator
(3R-trans)-3-((1-Carboxyethenyl)oxy)-4-hydroxy-1,5-cyclohexadiene-1-carboxylate	Generator
(3R,4R)-3-[(1-Carboxyethenyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid	Generator
Acid, chorismic	MeSH, HMDB
(-)-Chorismic acid	HMDB
(3R,4R)-3-[(1-Carboxyethenyl)oxy]-4-hydroxy-1,5-cyclohexadiene-1-carboxylic acid	HMDB
(3R-trans)-3-(1-Carboxyvinyloxy)-4-hydroxy-1,5-cyclohexadiene-1-carboxylic acid	HMDB

Molecular Formula

C₁₀H₁₀O₆

Average Mass

226.1828

Monoisotopic Mass

226.047738052

IUPAC Name

(3R,4R)-3-[(1-carboxyeth-1-en-1-yl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid

Traditional Name

chorismic acid

CAS Registry Number

55508-12-8

SMILES

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

InChI Identifier

InChI=1S/C10H10O6/c1-5(9(12)13)16-8-4-6(10(14)15)2-3-7(8)11/h2-4,7-8,11H,1H2,(H,12,13)(H,14,15)/t7-,8-/m1/s1

InChI Key

WTFXTQVDAKGDEY-HTQZYQBOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic acids and derivatives

Alternative Parents

Substituents

Dicarboxylic acid or derivatives
Secondary alcohol
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

5-[(1-carboxyethenyl)oxy]-6-hydroxycyclohexa-1,3-diene-1-carboxylic acid (CHEBI:17333 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	8.8 g/L	ALOGPS
logP	0.52	ALOGPS
logP	-0.13	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	3.39	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	54.31 m³·mol⁻¹	ChemAxon
Polarizability	20.49 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	545	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; River trout ; Rat ; Turkey ; Chicken ; Cattle ; Sheep ; Lion	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	433	Human feces; Human pleural fluid plaque; Human ; Cattle ; Pig ; Catfish	Metabolic reconstruction
Bacteria	Bacteroidetes	124	Human feces; Human ; Human appendix biopsy	Metabolic reconstruction
Bacteria	Actinobacteria	169	Human ; Human feces; Human pleural fluid plaque; Human dental plaque; Human sputum; Human nasopharyngeal swab; Cattle	Metabolic reconstruction
Bacteria	Fusobacteria	19	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5	Human feces; Cattle ; Human	Metabolic reconstruction
Bacteria	Verrucomicrobia	3	Human ; Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1	Human feces	Metabolic reconstruction
Bacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	10	Human feces; Human	Metabolic reconstruction
Bacteria	Deinococcus-Thermus	5
Eukaryota/Fungi	Ascomycota	12	Human feces	Unknown
Archaea/Archaea	Euryarchaeota	27	Human feces; Cattle ; Human	Metabolic reconstruction
Bacteria	Aquificae	2
Eukaryota/Fungi	Basidiomycota	5
Bacteria	Cyanobacteria	35	Human
Bacteria	Acidobacteria	3
Archaea/Archaea	Crenarchaeota	17	Human feces	Metabolic reconstruction
Bacteria	Chloroflexi	9
Bacteria	Chlamydiae	10	Human ; Sheep ; Cat
Bacteria	Chlorobi	11
Bacteria/NULL	Proteobacteria	3	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; River trout ; Rat ; Turkey ; Chicken ; Cattle ; Sheep ; Lion	Unknown; Metabolic reconstruction
Bacteria	Elusimicrobia	1
Archaea/Archaea	Korarchaeota	1
Bacteria	nah	1
Bacteria	Thermotogae	2
Bacteria/NULL	Actinobacteria	2	Human ; Human feces; Human pleural fluid plaque; Human dental plaque; Human sputum; Human nasopharyngeal swab; Cattle	Metabolic reconstruction
Eukaryota/Fungi	Mucoromycota	1	Human feces

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

HMDB0012199

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

Chorismic_acid

METLIN ID

Not Available

PubChem Compound

12039

PDB ID

ISJ

ChEBI ID

17333

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 Chorismate (MMDBc0029921)

MOL for #<Metabolite:0x0000560be2090968>

3D MOL for #<Metabolite:0x0000560be2090968>

3D SDF for #<Metabolite:0x0000560be2090968>

3D-SDF for #<Metabolite:0x0000560be2090968>

PDB for #<Metabolite:0x0000560be2090968>

3D PDB for #<Metabolite:0x0000560be2090968>

SMILES for #<Metabolite:0x0000560be2090968>

INCHI for #<Metabolite:0x0000560be2090968>

Structure for #<Metabolite:0x0000560be2090968>

3D Structure for #<Metabolite:0x0000560be2090968>