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Showing NP-Card for n-(2-sulfanylethyl)ethanimidic acid (NP0169034)

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Record Information
Version2.0
Created at2022-09-03 04:55:29 UTC
Updated at2022-09-03 04:55:29 UTC
NP-MRD IDNP0169034
Secondary Accession NumbersNone
Natural Product Identification
Common Namen-(2-sulfanylethyl)ethanimidic acid
DescriptionN-Acetylcysteamine belongs to the class of organic compounds known as acetamides. These are organic compounds with the general formula RNHC(=O)CH3, where R= organyl group. N-Acetylcysteamine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. n-(2-sulfanylethyl)ethanimidic acid is found in Trypanosoma brucei. n-(2-sulfanylethyl)ethanimidic acid was first documented in 2020 (PMID: 32628492). Based on a literature review a small amount of articles have been published on N-Acetylcysteamine (PMID: 36006794) (PMID: 35699427) (PMID: 35604200) (PMID: 33576128).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0169034 (n-(2-sulfanylethyl)ethanimidic acid)


  Mrv1652309032206552D          

  7  6  0  0  0  0            999 V2000
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  4  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
M  END
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3D MOL for NP0169034 (n-(2-sulfanylethyl)ethanimidic acid)

     RDKit          3D

 16 15  0  0  0  0  0  0  0  0999 V2000
   -1.8841    0.9591   -0.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4823   -0.2427    0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4074   -0.7952    1.4956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3192   -0.7871    0.5571 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6385   -0.1874   -0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0564   -0.6536   -0.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2162    0.1200   -1.1794 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2998    1.0543   -1.0654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9456    0.8066   -0.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7853    1.8917    0.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0238   -1.5535    1.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3428   -0.4681   -1.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6212    0.8972   -0.2316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.7582   -0.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3115   -0.4883    1.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8908    1.2053   -0.6071 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  3 11  1  0
  5 12  1  0
  5 13  1  0
  6 14  1  0
  6 15  1  0
  7 16  1  0
M  END
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3D SDF for NP0169034 (n-(2-sulfanylethyl)ethanimidic acid)


  Mrv1652309032206552D          

  7  6  0  0  0  0            999 V2000
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  4  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0169034

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)=NCCS

> <INCHI_IDENTIFIER>
InChI=1S/C4H9NOS/c1-4(6)5-2-3-7/h7H,2-3H2,1H3,(H,5,6)

> <INCHI_KEY>
AXFZADXWLMXITO-UHFFFAOYSA-N

> <FORMULA>
C4H9NOS

> <MOLECULAR_WEIGHT>
119.18

> <EXACT_MASS>
119.040485088

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
12.877744672680608

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-(2-sulfanylethyl)ethanimidic acid

> <ALOGPS_LOGP>
0.72

> <JCHEM_LOGP>
0.06589531611105658

> <ALOGPS_LOGS>
-1.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.113626660447512

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.804361423092377

> <JCHEM_PKA_STRONGEST_BASIC>
4.957585451956492

> <JCHEM_POLAR_SURFACE_AREA>
32.59

> <JCHEM_REFRACTIVITY>
32.3592

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.40e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-(2-sulfanylethyl)ethanimidic acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0169034 (n-(2-sulfanylethyl)ethanimidic acid)

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PDB for NP0169034 (n-(2-sulfanylethyl)ethanimidic acid)
HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0      -3.080  -2.667   0.000  0.00  0.00           S+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END

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3D PDB for NP0169034 (n-(2-sulfanylethyl)ethanimidic acid)
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SMILES for NP0169034 (n-(2-sulfanylethyl)ethanimidic acid)
CC(O)=NCCS
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INCHI for NP0169034 (n-(2-sulfanylethyl)ethanimidic acid)
InChI=1S/C4H9NOS/c1-4(6)5-2-3-7/h7H,2-3H2,1H3,(H,5,6)
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Synonyms
ValueSource
2-AcetamidoethanethiolChEBI
N-Acetyl-beta-mercaptoethylamineHMDB
TNA-mercaptoethylamineHMDB
Thiol N-acetyl-beta-mercaptoethylamineHMDB
Chemical FormulaC4H9NOS
Average Mass119.1800 Da
Monoisotopic Mass119.04049 Da
IUPAC NameN-(2-sulfanylethyl)ethanimidic acid
Traditional NameN-(2-sulfanylethyl)ethanimidic acid
CAS Registry NumberNot Available
SMILES
CC(O)=NCCS
InChI Identifier
InChI=1S/C4H9NOS/c1-4(6)5-2-3-7/h7H,2-3H2,1H3,(H,5,6)
InChI KeyAXFZADXWLMXITO-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
Trypanosoma bruceiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acetamides. These are organic compounds with the general formula RNHC(=O)CH3, where R= organyl group.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassCarboxylic acid derivatives  
Direct ParentAcetamides  
Alternative Parents
Substituents
  • Acetamide
    • 

  • Secondary carboxylic acid amide
    • 

  • Alkylthiol
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organosulfur compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Carbonyl group
    • 

  • 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
logP0.72ALOGPS
logP0.066ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)6.8ChemAxon
pKa (Strongest Basic)4.96ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area32.59 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity32.36 m³·mol⁻¹ChemAxon
Polarizability12.88 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0255064  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID13829  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14484  
PDB IDNot Available
ChEBI ID74410  
Good Scents IDNot Available
References
General References
  1. Brazeau-Henrie JT, Paquette AR, O'Rourke AQ, Darnowski MG, Boddy CN: Total and Chemoenzymatic Synthesis of Seongsanamide E. Org Lett. 2022 Sep 9;24(35):6369-6373. doi: 10.1021/acs.orglett.2c02271. Epub  2022 Aug 25. [PubMed:36006794  ] 
  2. Kim MS, Bae M, Song MC, Hwang S, Oh DC, Yoon YJ: Cyclodimerization of Mohangamide A by Thioesterase Domain Is Directed by Substrates. Org Lett. 2022 Jun 24;24(24):4444-4448. doi: 10.1021/acs.orglett.2c01670. Epub  2022 Jun 14. [PubMed:35699427  ] 
  3. Riuttamaki S, Laczko G, Madarasz A, Foldes T, Papai I, Bannykh A, Pihko PM: Carboxylate Catalyzed Isomerization of beta,gamma-Unsaturated N-Acetylcysteamine Thioesters. Chemistry. 2022 Aug 10;28(45):e202201030. doi: 10.1002/chem.202201030. Epub 2022  Jun 20. [PubMed:35604200  ] 
  4. Wormer GJ, Villadsen NL, Norby P, Poulsen TB: Concise Asymmetric Syntheses of Streptazone A and Abikoviromycin*. Angew Chem Int Ed Engl. 2021 May 3;60(19):10521-10525. doi:  10.1002/anie.202101439. Epub 2021 Mar 18. [PubMed:33576128  ] 
  5. Du YE, Byun WS, Lee SB, Hwang S, Shin YH, Shin B, Jang YJ, Hong S, Shin J, Lee SK, Oh DC: Formicins, N-Acetylcysteamine-Bearing Indenone Thioesters from a Wood Ant-Associated Bacterium. Org Lett. 2020 Jul 17;22(14):5337-5341. doi: 10.1021/acs.orglett.0c01584. Epub  2020 Jul 6. [PubMed:32628492  ] 
  6. LOTUS database [Link]