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Showing NP-Card for n-(2-oxothiolan-3-yl)ethanimidic acid (NP0166885)

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Record Information
Version2.0
Created at2022-09-03 02:20:53 UTC
Updated at2022-09-03 02:20:53 UTC
NP-MRD IDNP0166885
Secondary Accession NumbersNone
Natural Product Identification
Common Namen-(2-oxothiolan-3-yl)ethanimidic acid
DescriptionCitiolone, also known as thioxidrene or cythiolone, belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom. Citiolone is a moderately basic compound (based on its pKa). The drug has been shown to protect hamster cells subjected to temperature conditions of 8-25oC. Citiolone is a drug used in liver therapy. Citilone has also been studied with regards to hypothermia due to it being a hydroxyl free radical scavenger. It is a derivative of the amino acid cysteine.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0166885 (n-(2-oxothiolan-3-yl)ethanimidic acid)


  Mrv1572004221605002D          

 10 10  0  0  0  0            999 V2000
   -1.8405    1.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0558    1.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4427    2.2433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  5  1  0  0  0  0
  7  4  2  0  0  0  0
  7  5  1  4  0  0  0
  8  4  1  0  0  0  0
  9  6  2  0  0  0  0
 10  3  1  0  0  0  0
 10  6  1  0  0  0  0
M  END
Download

3D MOL for NP0166885 (n-(2-oxothiolan-3-yl)ethanimidic acid)

     RDKit          3D

 19 19  0  0  0  0  0  0  0  0999 V2000
    3.0904   -0.2286    0.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7719    0.2558   -0.0890 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7062    1.5289   -0.6320 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7169   -0.4653   -0.0078 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5892   -0.0268   -0.4607 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5013    0.0199    0.7025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9219   -0.1482    0.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7612   -1.3334   -1.0760 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0620   -0.9600   -1.4664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4457   -1.4104   -2.3950 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1655   -0.1897    1.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1802   -1.2894    0.0554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9102    0.3764   -0.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5741    2.3637   -0.0719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4307    1.0090   -0.8801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3988    1.0414    1.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1593   -0.6859    1.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3773    0.7519   -0.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4678   -0.6090    1.1615 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
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9  5  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  5 15  1  6
  6 16  1  0
  6 17  1  0
  7 18  1  0
  7 19  1  0
M  END
Download

3D SDF for NP0166885 (n-(2-oxothiolan-3-yl)ethanimidic acid)


  Mrv1572004221605002D          

 10 10  0  0  0  0            999 V2000
   -1.8405    1.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0558    1.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4427    2.2433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  5  1  0  0  0  0
  7  4  2  0  0  0  0
  7  5  1  4  0  0  0
  8  4  1  0  0  0  0
  9  6  2  0  0  0  0
 10  3  1  0  0  0  0
 10  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0166885

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)=NC1CCSC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H9NO2S/c1-4(8)7-5-2-3-10-6(5)9/h5H,2-3H2,1H3,(H,7,8)

> <INCHI_KEY>
NRFJZTXWLKPZAV-UHFFFAOYSA-N

> <FORMULA>
C6H9NO2S

> <MOLECULAR_WEIGHT>
159.2

> <EXACT_MASS>
159.035399708

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
15.455582723468513

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-(2-oxothiolan-3-yl)ethanimidic acid

> <ALOGPS_LOGP>
0.01

> <JCHEM_LOGP>
0.38811185499999956

> <ALOGPS_LOGS>
-1.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.784525967208621

> <JCHEM_PKA_STRONGEST_BASIC>
1.7897807851179148

> <JCHEM_POLAR_SURFACE_AREA>
49.660000000000004

> <JCHEM_REFRACTIVITY>
39.7246

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.12e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
citiolone

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0166885 (n-(2-oxothiolan-3-yl)ethanimidic acid)

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PDB for NP0166885 (n-(2-oxothiolan-3-yl)ethanimidic acid)
HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0      -3.436   3.633   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.971   3.157   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -1.651   1.651   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0      -0.826   4.188   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
HETATM   10  S   UNK     0       2.306   1.175   0.000  0.00  0.00           S+0
CONECT    1    4                                                            
CONECT    2    3    5                                                       
CONECT    3    2   10                                                       
CONECT    4    1    7    8                                                  
CONECT    5    2    6    7                                                  
CONECT    6    5    9   10                                                  
CONECT    7    4    5                                                       
CONECT    8    4                                                            
CONECT    9    6                                                            
CONECT   10    3    6                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for NP0166885 (n-(2-oxothiolan-3-yl)ethanimidic acid)
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SMILES for NP0166885 (n-(2-oxothiolan-3-yl)ethanimidic acid)
CC(O)=NC1CCSC1=O
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INCHI for NP0166885 (n-(2-oxothiolan-3-yl)ethanimidic acid)
InChI=1S/C6H9NO2S/c1-4(8)7-5-2-3-10-6(5)9/h5H,2-3H2,1H3,(H,7,8)
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View in JSmol
Synonyms
ValueSource
Citiolone, (+-)-isomerMeSH
ThioxidreneMeSH
CythioloneMeSH
N-Acetylhomocysteine thiolactoneMeSH
ReducdynMeSH
N-(2-Oxothiolan-3-yl)ethanimidateGenerator
Chemical FormulaC6H9NO2S
Average Mass159.2000 Da
Monoisotopic Mass159.03540 Da
IUPAC NameN-(2-oxothiolan-3-yl)ethanimidic acid
Traditional Namecitiolone
CAS Registry NumberNot Available
SMILES
CC(O)=NC1CCSC1=O
InChI Identifier
InChI=1S/C6H9NO2S/c1-4(8)7-5-2-3-10-6(5)9/h5H,2-3H2,1H3,(H,7,8)
InChI KeyNRFJZTXWLKPZAV-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 OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentN-acyl-alpha amino acids and derivatives  
Alternative Parents
Substituents
  • N-acyl-alpha amino acid or derivatives
    • 

  • Carbothioic s-lactone
    • 

  • Thiolane
    • 

  • Thiocarboxylic acid ester
    • 

  • Thiolactone
    • 

  • Carboximidic acid
    • 

  • Carboximidic acid derivative
    • 

  • Thiocarboxylic acid or derivatives
    • 

  • Organoheterocyclic compound
    • 

  • Organic 1,3-dipolar compound
    • 

  • Propargyl-type 1,3-dipolar organic compound
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
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
logP0.01ALOGPS
logP0.39ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)5.78ChemAxon
pKa (Strongest Basic)1.79ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.66 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity39.72 m³·mol⁻¹ChemAxon
Polarizability15.46 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB13442  
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCitiolone  
METLIN IDNot Available
PubChem Compound14520  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]