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Showing NP-Card for Glyoxal (NP0047201)

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Record Information
Version2.0
Created at2022-03-17 20:36:17 UTC
Updated at2022-03-17 20:36:17 UTC
NP-MRD IDNP0047201
Secondary Accession NumbersNone
Natural Product Identification
Common NameGlyoxal
Description Glyoxal was first documented in 1998 (PMID: 9506998).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047201 (Glyoxal)


  Mrv0541 02241221452D          

  4  3  0  0  0  0            999 V2000
    0.1105    0.4125    0.0000 O   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
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
M  END
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3D MOL for NP0047201 (Glyoxal)

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3D SDF for NP0047201 (Glyoxal)

  Mrv0541 02241221452D          

  4  3  0  0  0  0            999 V2000
    0.1105    0.4125    0.0000 O   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
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0047201

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=CC=O

> <INCHI_IDENTIFIER>
InChI=1S/C2H2O2/c3-1-2-4/h1-2H

> <INCHI_KEY>
LEQAOMBKQFMDFZ-UHFFFAOYSA-N

> <FORMULA>
C2H2O2

> <MOLECULAR_WEIGHT>
58.0361

> <EXACT_MASS>
58.005479308

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
4.502912633244565

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
oxaldehyde

> <ALOGPS_LOGP>
-0.04

> <JCHEM_LOGP>
-0.003598507333333334

> <ALOGPS_LOGS>
0.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.771710838961624

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
12.561399999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.18e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glyoxal

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0047201 (Glyoxal)
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PDB for NP0047201 (Glyoxal)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       0.206   0.770   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.207   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3                                                            
MASTER        0    0    0    0    0    0    0    0    4    0    6    0
END

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3D PDB for NP0047201 (Glyoxal)
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SMILES for NP0047201 (Glyoxal)
O=CC=O
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INCHI for NP0047201 (Glyoxal)
InChI=1S/C2H2O2/c3-1-2-4/h1-2H
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View in JSmol
Synonyms
ValueSource
1,2-EthanedioneChEBI
BiformalChEBI
BiformylChEBI
DiformalChEBI
DiformylChEBI
Ethane-1,2-dialChEBI
EthanedialChEBI
Glyoxal aldehydeChEBI
GlyoxylaldehydeChEBI
OxalChEBI
OxalaldehydeChEBI
EthanedioneMeSH
Chemical FormulaC2H2O2
Average Mass58.0361 Da
Monoisotopic Mass58.00548 Da
IUPAC Nameoxaldehyde
Traditional Nameglyoxal
CAS Registry Number107-22-2
SMILES
O=CC=O
InChI Identifier
InChI=1S/C2H2O2/c3-1-2-4/h1-2H
InChI KeyLEQAOMBKQFMDFZ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Sesamum indicumFooDB
Solanum lycopersicum var. lycopersicumFooDB
Zingiber officinaleFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as short-chain aldehydes. These are an aldehyde with a chain length containing between 2 and 5 carbon atoms.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentShort-chain aldehydes  
Alternative Parents
Substituents
  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Short-chain aldehyde
    • 

  • 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-0.04ALOGPS
logP-0.0036ChemAxon
logS0.57ALOGPS
pKa (Strongest Basic)-7.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity12.56 m³·mol⁻¹ChemAxon
Polarizability4.5 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB007802  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC14448  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGlyoxal  
METLIN IDNot Available
PubChem Compound7860  
PDB IDNot Available
ChEBI ID34779  
Good Scents IDNot Available
References
General References
  1. Uter W, Schwanitz HJ, Lessmann H, Schnuch A: Glyoxal is an important allergen for (medical care) cleaning staff. Int J Hyg Environ Health. 2001 Dec;204(4):251-3. doi: 10.1078/1438-4639-00099. [PubMed:11833298  ] 
  2. Aalto-Korte K, Makela EA, Huttunen M, Suuronen K, Jolanki R: Occupational contact allergy to glyoxal. Contact Dermatitis. 2005 May;52(5):276-81. doi: 10.1111/j.0105-1873.2005.00580.x. [PubMed:15899002  ] 
  3. Yamawaki H, Hara Y: Glyoxal causes inflammatory injury in human vascular endothelial cells. Biochem Biophys Res Commun. 2008 May 16;369(4):1155-9. doi: 10.1016/j.bbrc.2008.03.020. Epub 2008 Mar 14. [PubMed:18343213  ] 
  4. Thornalley PJ: Protein and nucleotide damage by glyoxal and methylglyoxal in physiological systems--role in ageing and disease. Drug Metabol Drug Interact. 2008;23(1-2):125-50. doi: 10.1515/dmdi.2008.23.1-2.125. [PubMed:18533367  ] 
  5. Zhang Z, Zhao D, Xu B: Analysis of glyoxal and related substances by means of high-performance liquid chromatography with refractive index detection. J Chromatogr Sci. 2013 Nov-Dec;51(10):893-8. doi: 10.1093/chromsci/bms186. Epub 2012 Nov 23. [PubMed:23180757  ] 
  6. Salter RJ, Blitz MA, Heard DE, Pilling MJ, Seakins PW: Pressure and temperature dependent photolysis of glyoxal in the 355-414 nm region: evidence for dissociation from multiple states. Phys Chem Chem Phys. 2013 May 7;15(17):6516-26. doi: 10.1039/c3cp43596b. [PubMed:23531876  ] 
  7. Lee C, Kim I, Park C: Glyoxal detoxification in Escherichia coli K-12 by NADPH dependent aldo-keto reductases. J Microbiol. 2013 Aug;51(4):527-30. doi: 10.1007/s12275-013-3087-8. Epub 2013 Aug 30. [PubMed:23990306  ] 
  8. Shamsi FA, Partal A, Sady C, Glomb MA, Nagaraj RH: Immunological evidence for methylglyoxal-derived modifications in vivo. Determination of antigenic epitopes. J Biol Chem. 1998 Mar 20;273(12):6928-36. doi: 10.1074/jbc.273.12.6928. [PubMed:9506998  ]