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Showing metabocard for Citiolone (HMDB0250301)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 07:18:16 UTC
Update Date2021-09-26 23:01:41 UTC
HMDB IDHMDB0250301
Secondary Accession NumbersNone
Metabolite Identification
Common NameCitiolone
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. This compound has been identified in human blood as reported by (PMID: 31557052 ). Citiolone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Citiolone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0250301 (Citiolone)

  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
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3D MOL for HMDB0250301 (Citiolone)

HMDB0250301
     RDKit          3D
Citiolone
 19 19  0  0  0  0  0  0  0  0999 V2000
    3.1280   -0.1091    0.4805 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7680   -0.0832   -0.1312 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6471    0.3546   -1.4355 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7154   -0.4457    0.4929 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5554   -0.3827   -0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3745    0.6806    0.4799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7679    0.6374   -0.0717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0111   -1.1624   -0.3584 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2941   -1.6596   -0.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8107   -2.7395    0.0544 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2779   -1.0777    1.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2930    0.7264    1.1841 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9008   -0.0823   -0.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1480    1.1774   -1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4071   -0.1565   -1.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3338    0.5336    1.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9362    1.6605    0.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4680    0.9101    0.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9194    1.2182   -0.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  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  0
  6 16  1  0
  6 17  1  0
  7 18  1  0
  7 19  1  0
M  END
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3D SDF for HMDB0250301 (Citiolone)

  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>
HMDB0250301

> <DATABASE_NAME>
hmdb

> <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 HMDB0250301 (Citiolone)

HMDB0250301
     RDKit          3D
Citiolone
 19 19  0  0  0  0  0  0  0  0999 V2000
    3.1280   -0.1091    0.4805 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7680   -0.0832   -0.1312 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6471    0.3546   -1.4355 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7154   -0.4457    0.4929 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5554   -0.3827   -0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3745    0.6806    0.4799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7679    0.6374   -0.0717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0111   -1.1624   -0.3584 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2941   -1.6596   -0.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8107   -2.7395    0.0544 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2779   -1.0777    1.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2930    0.7264    1.1841 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9008   -0.0823   -0.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1480    1.1774   -1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4071   -0.1565   -1.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3338    0.5336    1.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9362    1.6605    0.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4680    0.9101    0.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9194    1.2182   -0.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  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  0
  6 16  1  0
  6 17  1  0
  7 18  1  0
  7 19  1  0
M  END
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PDB for HMDB0250301 (Citiolone)

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 HMDB0250301 (Citiolone)

COMPND    HMDB0250301
HETATM    1  C1  UNL     1       3.128  -0.109   0.481  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.768  -0.083  -0.131  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.647   0.355  -1.435  1.00  0.00           O  
HETATM    4  N1  UNL     1       0.715  -0.446   0.493  1.00  0.00           N  
HETATM    5  C3  UNL     1      -0.555  -0.383  -0.190  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.375   0.681   0.480  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.768   0.637  -0.072  1.00  0.00           C  
HETATM    8  S1  UNL     1      -3.011  -1.162  -0.358  1.00  0.00           S  
HETATM    9  C6  UNL     1      -1.294  -1.660  -0.121  1.00  0.00           C  
HETATM   10  O2  UNL     1      -0.811  -2.740   0.054  1.00  0.00           O  
HETATM   11  H1  UNL     1       3.278  -1.078   1.022  1.00  0.00           H  
HETATM   12  H2  UNL     1       3.293   0.726   1.184  1.00  0.00           H  
HETATM   13  H3  UNL     1       3.901  -0.082  -0.312  1.00  0.00           H  
HETATM   14  H4  UNL     1       1.148   1.177  -1.729  1.00  0.00           H  
HETATM   15  H5  UNL     1      -0.407  -0.157  -1.285  1.00  0.00           H  
HETATM   16  H6  UNL     1      -1.334   0.534   1.562  1.00  0.00           H  
HETATM   17  H7  UNL     1      -0.936   1.661   0.195  1.00  0.00           H  
HETATM   18  H8  UNL     1      -3.468   0.910   0.746  1.00  0.00           H  
HETATM   19  H9  UNL     1      -2.919   1.218  -0.975  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    4    4
CONECT    3   14
CONECT    4    5
CONECT    5    6    9   15
CONECT    6    7   16   17
CONECT    7    8   18   19
CONECT    8    9
CONECT    9   10   10
END
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SMILES for HMDB0250301 (Citiolone)

CC(O)=NC1CCSC1=O
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INCHI for HMDB0250301 (Citiolone)

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 JSmolView Stereo Labels
Synonyms
ValueSource
Citiolone, (+-)-isomerMeSH
ThioxidreneMeSH
CythioloneMeSH
N-Acetylhomocysteine thiolactoneMeSH
ReducdynMeSH
N-(2-Oxothiolan-3-yl)ethanimidateGenerator
Chemical FormulaC6H9NO2S
Average Molecular Weight159.2
Monoisotopic Molecular Weight159.035399708
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
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
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB13442
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]