MiMeDB: Showing metabocard for cis-4-Hydroxycyclohexylacetic acid (MMDBc0000345)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:35:48 UTC

Update Date

2024-04-30 19:31:53 UTC

Metabolite ID

MMDBc0000345

Metabolite Identification

Common Name

cis-4-Hydroxycyclohexylacetic acid

Description

cis-4-Hydroxycyclohexylacetic acid is a tyrosine metabolite that has been found in the urine of a patient with a defect of 4-hydroxyphenylpyruvate dioxygenase (or HPPD) (EC 1.13.11.27), an inborn error of metabolism (PMIDs 701419, 719903) also called hawkinsinuria. 4-Hydroxyphenylpyruvate dioxygenase participates in the tyrosine catabolic pathway by catalyzing the conversion of 4-hydroxyphenylpyruvate to homogentisate (Hager et al., 1957). The mechanism of action of 4-hydroxyphenylpyruvate dioxygenase involves a decarboxylation step and an oxidation step, followed by a rearrangement step to form homogentisic acid (Tomoeda et al., 2000). Awata et al. (1994) determined that the HPD gene contains 14 exons. Analysis of the 5-prime flanking sequence of the gene suggested that expression of the gene is regulated by hepatocyte-specific and liver-enriched transcription factors, as well as by hormones (OMIM: 609695 ). cis-4-Hydroxycyclohexylacetic acid has also been found to be a microbial metabolite (PMID: 20615997 ).

Structure

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

Synonyms

Value	Source
cis-4-Hydroxycyclohexylacetate	Generator
4-Hydroxy-cyclohexylessigsaeure	HMDB
4-Hydroxycyclohexylacetate	HMDB
4-Hydroxycyclohexylacetic acid	HMDB
2-(4-Hydroxycyclohexyl)acetate	HMDB

Molecular Formula

C₈H₁₄O₃

Average Mass

158.195

Monoisotopic Mass

158.094294314

IUPAC Name

2-(4-hydroxycyclohexyl)acetic acid

Traditional Name

4-hydroxycyclohexylacetate

CAS Registry Number

Not Available

SMILES

OC1CCC(CC(O)=O)CC1

InChI Identifier

InChI=1S/C8H14O3/c9-7-3-1-6(2-4-7)5-8(10)11/h6-7,9H,1-5H2,(H,10,11)

InChI Key

ALTAAUJNHYWOGS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Cyclohexanols

Alternative Parents

Substituents

Cyclohexanol
Cyclic alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	27.1 g/L	ALOGPS
logP	0.93	ALOGPS
logP	0.69	ChemAxon
logS	-0.77	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	40.09 m³·mol⁻¹	ChemAxon
Polarizability	16.85 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 (Non-derivatized) - 70eV, Positive	splash10-0005-9400000000-abc03a0f8f17c7d423a2	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00g0-6950000000-e954349d2bba3a1f7bda	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052f-2900000000-cdb682550fd7986a0a1c	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ot-9800000000-a24c028ad8e3ba7b5049	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00o4-9000000000-3cefeadb5ca0dbfbb8e7	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-1900000000-228641a4fa5e65521acf	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bt9-3900000000-2731aa44b1316101793f	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4m-9300000000-382927881c2cd816ee47	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-74b6873659b7a591064c	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-3900000000-aec6e520c4013fbac56c	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-e2229c7ab1d4ae401bf2	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0005-7900000000-8822dbd01cb75d38d099	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000w-9300000000-94fda51f4a569a75c11e	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05po-9000000000-a9825eb303905399d98c	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Feces
Urine

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

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Hawkinsinuria		Association	Human Urine	HMDB	10412819
Hawkinsinuria	Increased	Association	Human Urine	HMDB	26226126

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	10	Human feces; Human stool; Human ; Human saliva; Human urine; Human sputum; Human subgingival plaque; Human vaginal fluid; Human supragingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	230	1100	umol/mmol creatinine	Children (1 - 13 years old)	Male	Hawkinsinuria	HMDB	10412819
Human Urine	Detected and Quantified	5.6	57.3	umol/mmol creatinine	Newborn (0-30 days old)	Both	Hawkinsinuria	HMDB	26226126
Human Urine	Detected and Quantified	0	2.2	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	26226126
Human Feces	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	20669995
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	24029555
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Blood	Detected but not Quantified							HMDB

External Links

HMDB ID

HMDB0000451

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022054

KNApSAcK ID

Not Available

Chemspider ID

13628091

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12702257

PDB ID

Not Available

ChEBI ID

89344

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Duynhoven J, Vaughan EE, Jacobs DM, Kemperman RA, van Velzen EJ, Gross G, Roger LC, Possemiers S, Smilde AK, Dore J, Westerhuis JA, Van de Wiele T: Metabolic fate of polyphenols in the human superorganism. Proc Natl Acad Sci U S A. 2011 Mar 15;108 Suppl 1:4531-8. doi: 10.1073/pnas.1000098107. Epub 2010 Jun 25. [PubMed:20615997 ]

Showing metabocard for cis-4-Hydroxycyclohexylacetic acid (MMDBc0000345)

MOL for #<Metabolite:0x00007fdb1150c488>

3D MOL for #<Metabolite:0x00007fdb1150c488>

3D SDF for #<Metabolite:0x00007fdb1150c488>

3D-SDF for #<Metabolite:0x00007fdb1150c488>

PDB for #<Metabolite:0x00007fdb1150c488>

3D PDB for #<Metabolite:0x00007fdb1150c488>

SMILES for #<Metabolite:0x00007fdb1150c488>

INCHI for #<Metabolite:0x00007fdb1150c488>

Structure for #<Metabolite:0x00007fdb1150c488>

3D Structure for #<Metabolite:0x00007fdb1150c488>