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Showing NP-Card for n-(2-sulfoethyl)ethanimidic acid (NP0304031)

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Record Information
Version2.0
Created at2022-09-10 18:50:21 UTC
Updated at2022-09-10 18:50:22 UTC
NP-MRD IDNP0304031
Secondary Accession NumbersNone
Natural Product Identification
Common Namen-(2-sulfoethyl)ethanimidic acid
DescriptionN-Acetyltaurine, also known as atamg or nact, 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). An amino sulfonic acid that is taurine substituted by an acetyl group at the N atom. n-(2-sulfoethyl)ethanimidic acid is found in Synechococcus elongatus. n-(2-sulfoethyl)ethanimidic acid was first documented in 2012 (PMID: 22228769). N-Acetyltaurine is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 25833487) (PMID: 27520321).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0304031 (n-(2-sulfoethyl)ethanimidic acid)


  Mrv1652312111719142D          

 10  9  0  0  0  0            999 V2000
 2498.6690 2498.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.3836 2499.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.0984 2498.7642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.8132 2499.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.5282 2498.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.8132 2500.0011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.9540 2499.1758    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 2497.5403 2499.8926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2498.3658 2499.8926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.2351 2498.7621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  2  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
M  END
Download

3D MOL for NP0304031 (n-(2-sulfoethyl)ethanimidic acid)

     RDKit          3D

 19 18  0  0  0  0  0  0  0  0999 V2000
    3.0173    0.2337    0.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9380    0.4719   -0.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1565    1.3275   -1.0886 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7217   -0.2547   -0.1067 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2845    0.0253   -1.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5458   -0.7362   -0.9855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3530   -0.4243    0.5606 S   0  0  0  0  0  6  0  0  0  0  0  0
   -1.5149   -0.9126    1.6959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6779   -1.1582    0.6371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7065    1.2285    0.6945 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6703    1.1236    0.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5333    0.0774    1.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6808   -0.6179    0.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5279   -0.9630    0.6188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5182    1.1259   -0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2146   -0.0681   -2.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4735   -1.8081   -1.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2421   -0.3257   -1.7758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1439    1.6550    1.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7 10  1  0
  7  8  2  0
  7  9  2  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
 10 19  1  0
M  END
Download

3D SDF for NP0304031 (n-(2-sulfoethyl)ethanimidic acid)


  Mrv1652312111719142D          

 10  9  0  0  0  0            999 V2000
 2498.6690 2498.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.3836 2499.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.0984 2498.7642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.8132 2499.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.5282 2498.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.8132 2500.0011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.9540 2499.1758    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 2497.5403 2499.8926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2498.3658 2499.8926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.2351 2498.7621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  2  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0304031

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C4H9NO4S

> <MOLECULAR_WEIGHT>
167.18

> <EXACT_MASS>
167.025228948

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
15.006627332279146

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-acetamidoethane-1-sulfonic acid

> <ALOGPS_LOGP>
-1.94

> <JCHEM_LOGP>
-2.9325552482268433

> <ALOGPS_LOGS>
-0.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.939475088402919

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.031482931108826

> <JCHEM_PKA_STRONGEST_BASIC>
-1.7007132426937215

> <JCHEM_POLAR_SURFACE_AREA>
83.47

> <JCHEM_REFRACTIVITY>
34.0489

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.64e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-acetamidoethanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0304031 (n-(2-sulfoethyl)ethanimidic acid)

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PDB for NP0304031 (n-(2-sulfoethyl)ethanimidic acid)
HEADER    PROTEIN                                 11-DEC-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-DEC-17         0                                  
HETATM    1  C   UNK     0    4664.1824664.360   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    4665.5164665.128   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    4666.8504664.360   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0    4668.1854665.128   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4669.5194664.360   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    4668.1854666.669   0.000  0.00  0.00           O+0
HETATM    7  S   UNK     0    4662.8474665.128   0.000  0.00  0.00           S+0
HETATM    8  O   UNK     0    4662.0754666.466   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    4663.6164666.466   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    4661.5054664.356   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    1    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END

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3D PDB for NP0304031 (n-(2-sulfoethyl)ethanimidic acid)
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SMILES for NP0304031 (n-(2-sulfoethyl)ethanimidic acid)
CC(=O)NCCS(O)(=O)=O
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INCHI for NP0304031 (n-(2-sulfoethyl)ethanimidic acid)
InChI=1S/C4H9NO4S/c1-4(6)5-2-3-10(7,8)9/h2-3H2,1H3,(H,5,6)(H,7,8,9)
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View in JSmol
Synonyms
ValueSource
2-Acetamidoethanesulfonic acidChEBI
2-AcetamidoethanesulfonateGenerator
2-AcetamidoethanesulphonateGenerator
2-Acetamidoethanesulphonic acidGenerator
Magnesium acetyltaurinateHMDB
ATaMgHMDB
AcetyltaurinateHMDB
Magnesium acetyltaurateHMDB
NATHMDB
AcetyltaurineHMDB
2-(Acetylamino)ethanesulfonic acidHMDB
[2-Acetylamino]ethanesulfonic acidHMDB
NAcTHMDB
Chemical FormulaC4H9NO4S
Average Mass167.1800 Da
Monoisotopic Mass167.02523 Da
IUPAC Name2-acetamidoethane-1-sulfonic acid
Traditional Name2-acetamidoethanesulfonic acid
CAS Registry NumberNot Available
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 KeyCXJAAWRLVGAKDV-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Synechococcus elongatusLOTUS Database
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).
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassOrganic sulfonic acids and derivatives  
Sub ClassOrganosulfonic acids and derivatives  
Direct ParentOrganosulfonic 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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.9ALOGPS
logP-2.9ChemAxon
logS-0.8ALOGPS
pKa (Strongest Acidic)-1ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.47 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity34.05 m³·mol⁻¹ChemAxon
Polarizability15.01 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0240253  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID140553  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkN-Acetyltaurine  
METLIN IDNot Available
PubChem Compound159864  
PDB IDNot Available
ChEBI ID84415  
Good Scents IDNot Available
References
General References
  1. 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  ] 
  2. Miyazaki T, Ishikura K, Honda A, Ra SG, Komine S, Miyamoto Y, Ohmori H, Matsuzaki Y: Increased N-acetyltaurine in serum and urine after endurance exercise in human. Adv Exp Med Biol. 2015;803:53-62. doi: 10.1007/978-3-319-15126-7_5. [PubMed:25833487  ] 
  3. 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  ] 
  4. LOTUS database [Link]