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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2017-12-11 17:01:58 UTC

Update Date

2023-02-21 17:33:47 UTC

HMDB ID

HMDB0240253

Secondary Accession Numbers

None

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Acetamidoethanesulfonic acid	ChEBI
2-Acetamidoethanesulfonate	Generator
2-Acetamidoethanesulphonate	Generator
2-Acetamidoethanesulphonic acid	Generator
NAT	HMDB
Acetyltaurine	HMDB
2-(Acetylamino)ethanesulfonic acid	HMDB
[2-Acetylamino]ethanesulfonic acid	HMDB
Magnesium acetyltaurinate	HMDB
ATaMg	HMDB
Acetyltaurinate	HMDB
Magnesium acetyltaurate	HMDB
NAcT	HMDB
N-Acetyltaurine	ChEBI

Chemical Formula

C₄H₉NO₄S

Average Molecular Weight

167.18

Monoisotopic Molecular Weight

167.025228948

IUPAC Name

2-acetamidoethane-1-sulfonic acid

Traditional Name

2-acetamidoethanesulfonic acid

CAS Registry Number

19213-70-8

SMILES

CC(=O)NCCS(O)(=O)=O

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

Description

Belongs to the class of organic compounds known as organosulfonic acids. Organosulfonic acids are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic sulfonic acids and derivatives

Sub Class

Organosulfonic acids and derivatives

Direct Parent

Organosulfonic acids

Alternative Parents

Substituents

Organosulfonic acid
Sulfonyl
Acetamide
Alkanesulfonic acid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

acetamides (CHEBI:84415 )
amino sulfonic acid (CHEBI:84415 )

Ontology

Not Available

Placenta (HMDB: HMDB0240253)

Excreta

Biofluid or Excreta

Urine (PMID: 27520321)
Feces (PMID: 27543620)

Source

Exogenous

Exogenous (HMDB: HMDB0240253)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-1.9	ALOGPS
logP	-2.9	ChemAxon
logS	-0.8	ALOGPS
pKa (Strongest Acidic)	-1	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.47 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	34.05 m³·mol⁻¹	ChemAxon
Polarizability	15.01 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M-H]-	131.1	31661259
AllCCS	[M+H]+	136.431	31661259
DeepCCS	[M+H]+	130.272	30932474
DeepCCS	[M-H]-	126.896	30932474
DeepCCS	[M-2H]-	163.773	30932474
DeepCCS	[M+Na]+	138.844	30932474
AllCCS	[M+H]+	136.4	32859911
AllCCS	[M+H-H2O]+	132.6	32859911
AllCCS	[M+NH4]+	140.0	32859911
AllCCS	[M+Na]+	141.0	32859911
AllCCS	[M-H]-	131.1	32859911
AllCCS	[M+Na-2H]-	133.5	32859911
AllCCS	[M+HCOO]-	136.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.02 minutes	32390414
Predicted by Siyang on May 30, 2022	8.6147 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.07 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	910.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	293.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	64.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	176.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	55.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	239.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	243.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	657.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	574.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	51.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	775.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	186.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	176.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	535.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	245.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	228.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Acetyltaurine	CC(=O)NCCS(O)(=O)=O	2939.4	Standard polar	33892256
N-Acetyltaurine	CC(=O)NCCS(O)(=O)=O	1401.0	Standard non polar	33892256
N-Acetyltaurine	CC(=O)NCCS(O)(=O)=O	1660.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Acetyltaurine,1TMS,isomer #1	CC(=O)NCCS(=O)(=O)O[Si](C)(C)C	1681.1	Semi standard non polar	33892256
N-Acetyltaurine,1TMS,isomer #1	CC(=O)NCCS(=O)(=O)O[Si](C)(C)C	1496.3	Standard non polar	33892256
N-Acetyltaurine,1TMS,isomer #1	CC(=O)NCCS(=O)(=O)O[Si](C)(C)C	2455.6	Standard polar	33892256
N-Acetyltaurine,1TMS,isomer #2	CC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C	1636.1	Semi standard non polar	33892256
N-Acetyltaurine,1TMS,isomer #2	CC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C	1594.0	Standard non polar	33892256
N-Acetyltaurine,1TMS,isomer #2	CC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C	2730.7	Standard polar	33892256
N-Acetyltaurine,2TMS,isomer #1	CC(=O)N(CCS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C	1684.1	Semi standard non polar	33892256
N-Acetyltaurine,2TMS,isomer #1	CC(=O)N(CCS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C	1743.9	Standard non polar	33892256
N-Acetyltaurine,2TMS,isomer #1	CC(=O)N(CCS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C	2141.1	Standard polar	33892256
N-Acetyltaurine,1TBDMS,isomer #1	CC(=O)NCCS(=O)(=O)O[Si](C)(C)C(C)(C)C	1953.7	Semi standard non polar	33892256
N-Acetyltaurine,1TBDMS,isomer #1	CC(=O)NCCS(=O)(=O)O[Si](C)(C)C(C)(C)C	1781.8	Standard non polar	33892256
N-Acetyltaurine,1TBDMS,isomer #1	CC(=O)NCCS(=O)(=O)O[Si](C)(C)C(C)(C)C	2555.2	Standard polar	33892256
N-Acetyltaurine,1TBDMS,isomer #2	CC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C(C)(C)C	1866.7	Semi standard non polar	33892256
N-Acetyltaurine,1TBDMS,isomer #2	CC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C(C)(C)C	1873.5	Standard non polar	33892256
N-Acetyltaurine,1TBDMS,isomer #2	CC(=O)N(CCS(=O)(=O)O)[Si](C)(C)C(C)(C)C	2763.6	Standard polar	33892256
N-Acetyltaurine,2TBDMS,isomer #1	CC(=O)N(CCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2162.7	Semi standard non polar	33892256
N-Acetyltaurine,2TBDMS,isomer #1	CC(=O)N(CCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2296.9	Standard non polar	33892256
N-Acetyltaurine,2TBDMS,isomer #1	CC(=O)N(CCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2286.5	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected and Quantified	0.599-1.38 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	27520321	details
Urine	Detected and Quantified	8.38 (5.39-10.47) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	27520321	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

140553

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

N-Acetyltaurine

METLIN ID

Not Available

PubChem Compound

159864

PDB ID

Not Available

ChEBI ID

84415

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

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 (HMDB0240253)

MOL for HMDB0240253 (N-Acetyltaurine)

3D MOL for HMDB0240253 (N-Acetyltaurine)

3D SDF for HMDB0240253 (N-Acetyltaurine)

3D-SDF for HMDB0240253 (N-Acetyltaurine)

PDB for HMDB0240253 (N-Acetyltaurine)

3D PDB for HMDB0240253 (N-Acetyltaurine)

SMILES for HMDB0240253 (N-Acetyltaurine)

INCHI for HMDB0240253 (N-Acetyltaurine)

Structure for HMDB0240253 (N-Acetyltaurine)

3D Structure for HMDB0240253 (N-Acetyltaurine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized