MiMeDB: Showing metabocard for Cis-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylate (MMDBc0049990)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:47:43 UTC

Update Date

2025-10-07 16:08:15 UTC

Metabolite ID

MMDBc0049990

Metabolite Identification

Common Name

Cis-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylate

Description

Cis-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylate is a dihydroxy derivative of cyclohexa-3,5-diene and belongs to the class of aromatic metabolites. This compound plays a crucial role in the biochemical pathways of aromatic compound degradation, particularly in the metabolism of phenolic compounds. It is formed through the action of specific enzymes, including phenol hydroxylase and benzoate dioxygenase, which facilitate the conversion of aromatic substrates into more polar metabolites. Subsequently, cis-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylate is further processed by cis-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylate dehydrogenase, contributing to the production of cis,cis-muconic acid, a key intermediate in the microbial degradation of aromatic compounds (PMID:11425226 ). The presence of hydroxyl groups in its structure enhances its reactivity and solubility, making it an important intermediate in various metabolic pathways that facilitate the breakdown of complex aromatic compounds into simpler forms that can be utilized or excreted by organisms.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(1R,2S)-1,2-Dihydroxycyclohexa-3,5-diene-1-carboxylic acid	ChEBI
cis-1,2-Dihydroxycyclohexa-3,5-diene-1-carboxylate	ChEBI
cis-1,6-Dihydroxy-2,4-cyclohexadiene-1-carboxylic acid	ChEBI
(1R,2S)-1,2-Dihydroxycyclohexa-3,5-diene-1-carboxylate	Generator
cis-1,2-Dihydroxycyclohexa-3,5-diene-1-carboxylic acid	Generator
cis-1,6-Dihydroxy-2,4-cyclohexadiene-1-carboxylate	Generator
(1R,6S)-1,6-Dihydroxycyclohexa-2,4-dienecarboxylate	Generator
(1R,6S)-1,6-Dihydroxycyclohexa-2,4-diene-1-carboxylic acid	Generator

Molecular Formula

C₇H₈O₄

Average Mass

156.137

Monoisotopic Mass

156.042258738

IUPAC Name

(1R,6S)-1,6-dihydroxycyclohexa-2,4-diene-1-carboxylic acid

Traditional Name

(1R,6S)-1,6-dihydroxycyclohexa-2,4-diene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C7H8O4/c8-5-3-1-2-4-7(5,11)6(9)10/h1-5,8,11H,(H,9,10)/t5-,7+/m0/s1

InChI Key

PUCYIVFXTPWJDD-CAHLUQPWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents

Substituents

Beta-hydroxy acid
Alpha-hydroxy acid
Tertiary alcohol
Secondary alcohol
1,2-diol
Monocarboxylic acid or derivatives
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

cis-1,6-dihydroxycyclohexa-2,4-dienecarboxylic acid (CHEBI:37888 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	165 g/L	ALOGPS
logP	-0.37	ALOGPS
logP	-0.5	ChemAxon
logS	0.02	ALOGPS
pKa (Strongest Acidic)	3.55	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	38.69 m³·mol⁻¹	ChemAxon
Polarizability	13.89 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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-7c206cdc309540a31bc8	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06ri-1900000000-9b01964c3a4f6939c021	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9000000000-4801174874496439f726	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-08fr-0900000000-8d005c7e74af2728b27f	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-08fr-0900000000-da5d2c160202dac0065b	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-08fu-8900000000-341e4fbcfa7a11f1a7db	2019-02-23	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	400.3
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	186.5
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-24	54.8
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	268.6
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	294.6
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	356.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	867.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	522.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	879.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	213.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	307.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	212.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	60.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	160.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	648.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	69.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	255.0
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	852.9
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	729.2

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Cis-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylate_TMS_1	C[Si](C)(C)O[C@H]1C=CC=C[C@]1(O)C(=O)O	standard non polar	2025-10-24	2074.47
Gas Chromatography	Cis-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylate_TMS_2	C[Si](C)(C)O[C@]1(C(=O)O)C=CC=C[C@@H]1O	standard non polar	2025-10-24	1632.45
Gas Chromatography	Cis-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylate_TMS_3	C[Si](C)(C)OC(=O)[C@@]1(O)C=CC=C[C@@H]1O	standard non polar	2025-10-24	2073.92
Gas Chromatography	Cis-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylate_TMS_4	C[Si](C)(C)O[C@H]1C=CC=C[C@]1(O[Si](C)(C)C)C(=O)O	standard non polar	2025-10-24	2358.02
Gas Chromatography	Cis-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylate_TMS_5	C[Si](C)(C)OC(=O)[C@@]1(O)C=CC=C[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-24	1749.36
Gas Chromatography	Cis-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylate_TMS_6	C[Si](C)(C)OC(=O)[C@@]1(O[Si](C)(C)C)C=CC=C[C@@H]1O	standard non polar	2025-10-24	2035.35
Gas Chromatography	Cis-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylate_TMS_7	C[Si](C)(C)OC(=O)[C@@]1(O[Si](C)(C)C)C=CC=C[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-24	981.983
Gas Chromatography	Cis-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylate_TMS_1	C[Si](C)(C)O[C@H]1C=CC=C[C@]1(O)C(=O)O	standard polar	2025-10-24	2041.94
Gas Chromatography	Cis-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylate_TMS_2	C[Si](C)(C)O[C@]1(C(=O)O)C=CC=C[C@@H]1O	standard polar	2025-10-24	2216.8
Gas Chromatography	Cis-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylate_TMS_3	C[Si](C)(C)OC(=O)[C@@]1(O)C=CC=C[C@@H]1O	standard polar	2025-10-24	1768.32
Gas Chromatography	Cis-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylate_TMS_4	C[Si](C)(C)O[C@H]1C=CC=C[C@]1(O[Si](C)(C)C)C(=O)O	standard polar	2025-10-24	1950.19
Gas Chromatography	Cis-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylate_TMS_5	C[Si](C)(C)OC(=O)[C@@]1(O)C=CC=C[C@@H]1O[Si](C)(C)C	standard polar	2025-10-24	1976.4
Gas Chromatography	Cis-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylate_TMS_6	C[Si](C)(C)OC(=O)[C@@]1(O[Si](C)(C)C)C=CC=C[C@@H]1O	standard polar	2025-10-24	1921.69
Gas Chromatography	Cis-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylate_TMS_7	C[Si](C)(C)OC(=O)[C@@]1(O[Si](C)(C)C)C=CC=C[C@@H]1O[Si](C)(C)C	standard polar	2025-10-24	1837.98

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/Eubacteria	Proteobacteria	40	Human ; Human feces; Human sputum; Human unknown	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	14	Human feces; Human	Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	6	Human feces; Human	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

C06321

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440977

PDB ID

Not Available

ChEBI ID

37888

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 ]

Showing metabocard for Cis-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylate (MMDBc0049990)

MOL for #<Metabolite:0x00007f2e2c25a790>

3D MOL for #<Metabolite:0x00007f2e2c25a790>

3D SDF for #<Metabolite:0x00007f2e2c25a790>

3D-SDF for #<Metabolite:0x00007f2e2c25a790>

PDB for #<Metabolite:0x00007f2e2c25a790>

3D PDB for #<Metabolite:0x00007f2e2c25a790>

SMILES for #<Metabolite:0x00007f2e2c25a790>

INCHI for #<Metabolite:0x00007f2e2c25a790>

Structure for #<Metabolite:0x00007f2e2c25a790>

3D Structure for #<Metabolite:0x00007f2e2c25a790>