MiMeDB: Showing metabocard for N-Acetyltaurine (MMDBc0000716)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:53:24 UTC

Update Date

2022-08-31 06:11:32 UTC

Metabolite ID

MMDBc0000716

Metabolite Identification

Common Name

N-Acetyltaurine

Description

N-Acetyltaurine (also known as NAT) is a highly water-soluble and hygroscopic compound formed by the acetylation of taurine. It is both an endogenous metabolite that is constitutively synthesized in the body and an exogenous metabolite formed by ethanol metabolism. NAT is formed by one or multiple N-acetylation reactions between taurine and ethanol metabolites (primarily acetate). The enzyme responsible for NAT synthesis is called NAT synthase, a cytosolic metalloenzyme located in the kidney and liver that can directly catalyze the esterification reaction between taurine and acetate, without the involvement of ATP and CoA. NAT is a potential biomarker of hyperacetatemia as well as ethanol consumption (PMID: 22228769 ). NAT is typically found in human urine with normal concentrations of 0.599-1.38 umol/mmol creatinine in alcohol-abstinent subjects. NAT can reach average levels of 8.38 umol/mmol creatinine (range 5.39-10.47 umol/mmol creatinine) in subjects consuming alcohol within 3 to 6 h after the start of drinking. Positive NAT results can be used as an indicator for recent alcohol consumption (PMID: 27520321 ). NAT is considered a direct alcohol biomarker that specifically represents the oxidative pathway of ethanol metabolism. Other direct alcohol biomarkers such as fatty acid ethyl esters (FAEE), ethyl glucuronide, ethyl sulfate, and phosphatidylethanol reflect the non-oxidative pathway of alcohol metabolism. NAT is also elevated in urine after periods of endurance exercise. NAT was previously found in nature as a major component in the sticky droplet of orb spider web. Due to its high hygroscopicity, N-acetyltaurine appears to ensure the orb spider’s web flexibility.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₄H₉NO₄S

Average Mass

167.18

Monoisotopic Mass

167.025228948

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

InChI=1S/C4H9NO4S/c1-4(6)5-2-3-10(7,8)9/h2-3H2,1H3,(H,5,6)(H,7,8,9)

InChI Key

CXJAAWRLVGAKDV-UHFFFAOYSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

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

Blood
Feces
Placenta
Urine

Tissue Locations

Placenta

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	Firmicutes	3	Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Age	Sex	Health Condition	Data Source	Reference
Human	Detected and Quantified		0.599	1.38	Adult (>18 years old)	Both	Normal	HMDB	27520321
Human	Detected and Quantified	8.38	5.39	10.47	Adult (>18 years old)	Both	Normal	HMDB	27520321
Human Placenta	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
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	Detected but not Quantified							HMDB

External Links

Not Available

General References

Shi X, Yao D, Chen C: Identification of N-acetyltaurine as a novel metabolite of ethanol through metabolomics-guided biochemical analysis. J Biol Chem. 2012 Feb 24;287(9):6336-49. doi: 10.1074/jbc.M111.312199. Epub 2012 Jan 6. [PubMed:22228769 ]
Luginbuhl M, Rutjens S, Konig S, Furrer J, Weinmann W: N-Acetyltaurine as a novel urinary ethanol marker in a drinking study. Anal Bioanal Chem. 2016 Oct;408(26):7529-36. doi: 10.1007/s00216-016-9855-7. Epub 2016 Aug 13. [PubMed:27520321 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for N-Acetyltaurine (MMDBc0000716)

MOL for #<Metabolite:0x0000560be23fadd8>

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3D PDB for #<Metabolite:0x0000560be23fadd8>

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Structure for #<Metabolite:0x0000560be23fadd8>

3D Structure for #<Metabolite:0x0000560be23fadd8>