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Showing metabocard for Ethylene glycol dinitrate (HMDB0252070)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 09:44:50 UTC
Update Date2021-09-26 23:04:26 UTC
HMDB IDHMDB0252070
Secondary Accession NumbersNone
Metabolite Identification
Common NameEthylene glycol dinitrate
Description2-(nitrooxy)ethyl nitrate belongs to the class of organic compounds known as alkyl nitrates. These are organic compounds containing a nitrate that is O-linked to an alkyl group. 2-(nitrooxy)ethyl nitrate is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Ethylene glycol dinitrate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Ethylene glycol dinitrate 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 HMDB0252070 (Ethylene glycol dinitrate)


  Mrv1652306031608002D          

 10  9  0  0  0  0            999 V2000
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  5  3  2  0  0  0  0
  6  3  2  0  0  0  0
  7  4  2  0  0  0  0
  8  4  2  0  0  0  0
  9  1  1  0  0  0  0
  9  3  1  0  0  0  0
 10  2  1  0  0  0  0
 10  4  1  0  0  0  0
M  END
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3D MOL for HMDB0252070 (Ethylene glycol dinitrate)

HMDB0252070
     RDKit          3D
Ethylene glycol dinitrate
 14 13  0  0  0  0  0  0  0  0999 V2000
    2.7140    2.2162   -0.4271 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7614    1.0154   -0.0566 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.9134    0.3271   -0.3748 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.6976    0.3631    0.4877 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7737   -0.4191   -0.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6014   -0.1149    0.3596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6169   -0.8636   -0.2613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9135   -0.5306   -0.0142 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.2734    0.4043    0.7139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9156   -1.3337   -0.5297 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.9989   -1.5098   -0.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7579   -0.1769   -1.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7807    0.9626    0.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5155   -0.3401    1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  5 11  1  0
  5 12  1  0
  6 13  1  0
  6 14  1  0
M  CHG  4   2   1   3  -1   8   1  10  -1
M  END
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3D SDF for HMDB0252070 (Ethylene glycol dinitrate)


  Mrv1652306031608002D          

 10  9  0  0  0  0            999 V2000
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  5  3  2  0  0  0  0
  6  3  2  0  0  0  0
  7  4  2  0  0  0  0
  8  4  2  0  0  0  0
  9  1  1  0  0  0  0
  9  3  1  0  0  0  0
 10  2  1  0  0  0  0
 10  4  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0252070

> <DATABASE_NAME>
hmdb

> <SMILES>
O=N(=O)OCCON(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C2H4N2O6/c5-3(6)9-1-2-10-4(7)8/h1-2H2

> <INCHI_KEY>
UQXKXGWGFRWILX-UHFFFAOYSA-N

> <FORMULA>
C2H4N2O6

> <MOLECULAR_WEIGHT>
152.062

> <EXACT_MASS>
152.006935857

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
10.63475553846055

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(nitrooxy)ethyl nitrate

> <ALOGPS_LOGP>
1.17

> <JCHEM_LOGP>
0.6412240293333334

> <ALOGPS_LOGS>
-2.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-5.800608910174464

> <JCHEM_POLAR_SURFACE_AREA>
110.1

> <JCHEM_REFRACTIVITY>
27.9416

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethylene glycol dinitrate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0252070 (Ethylene glycol dinitrate)

HMDB0252070
     RDKit          3D
Ethylene glycol dinitrate
 14 13  0  0  0  0  0  0  0  0999 V2000
    2.7140    2.2162   -0.4271 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7614    1.0154   -0.0566 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.9134    0.3271   -0.3748 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.6976    0.3631    0.4877 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7737   -0.4191   -0.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6014   -0.1149    0.3596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6169   -0.8636   -0.2613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9135   -0.5306   -0.0142 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.2734    0.4043    0.7139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9156   -1.3337   -0.5297 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.9989   -1.5098   -0.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7579   -0.1769   -1.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7807    0.9626    0.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5155   -0.3401    1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  5 11  1  0
  5 12  1  0
  6 13  1  0
  6 14  1  0
M  CHG  4   2   1   3  -1   8   1  10  -1
M  END
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PDB for HMDB0252070 (Ethylene glycol dinitrate)

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       5.335  -0.000   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      -1.334   0.770   0.000  0.00  0.00           N+0
HETATM    5  O   UNK     0       6.668   0.770   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       5.335  -1.540   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.001   0.770   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    9                                                       
CONECT    2    1   10                                                       
CONECT    3    5    6    9                                                  
CONECT    4    7    8   10                                                  
CONECT    5    3                                                            
CONECT    6    3                                                            
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    1    3                                                       
CONECT   10    2    4                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for HMDB0252070 (Ethylene glycol dinitrate)

COMPND    HMDB0252070
HETATM    1  O1  UNL     1       2.714   2.216  -0.427  1.00  0.00           O  
HETATM    2  N1  UNL     1       2.761   1.015  -0.057  1.00  0.00           N1+
HETATM    3  O2  UNL     1       3.913   0.327  -0.375  1.00  0.00           O1-
HETATM    4  O3  UNL     1       1.698   0.363   0.488  1.00  0.00           O  
HETATM    5  C1  UNL     1       0.774  -0.419  -0.224  1.00  0.00           C  
HETATM    6  C2  UNL     1      -0.601  -0.115   0.360  1.00  0.00           C  
HETATM    7  O4  UNL     1      -1.617  -0.864  -0.261  1.00  0.00           O  
HETATM    8  N2  UNL     1      -2.913  -0.531  -0.014  1.00  0.00           N1+
HETATM    9  O5  UNL     1      -3.273   0.404   0.714  1.00  0.00           O  
HETATM   10  O6  UNL     1      -3.916  -1.334  -0.530  1.00  0.00           O1-
HETATM   11  H1  UNL     1       0.999  -1.510  -0.142  1.00  0.00           H  
HETATM   12  H2  UNL     1       0.758  -0.177  -1.298  1.00  0.00           H  
HETATM   13  H3  UNL     1      -0.781   0.963   0.159  1.00  0.00           H  
HETATM   14  H4  UNL     1      -0.516  -0.340   1.449  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    4    5
CONECT    5    6   11   12
CONECT    6    7   13   14
CONECT    7    8
CONECT    8    9    9   10
END
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SMILES for HMDB0252070 (Ethylene glycol dinitrate)

O=N(=O)OCCON(=O)=O
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INCHI for HMDB0252070 (Ethylene glycol dinitrate)

InChI=1S/C2H4N2O6/c5-3(6)9-1-2-10-4(7)8/h1-2H2
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2-(Nitrooxy)ethyl nitric acidGenerator
Ethylene glycol dinitrateMeSH
NitroglycolMeSH
Ethylene dinitric acidGenerator
Chemical FormulaC2H4N2O6
Average Molecular Weight152.062
Monoisotopic Molecular Weight152.006935857
IUPAC Name2-(nitrooxy)ethyl nitrate
Traditional Nameethylene glycol dinitrate
CAS Registry NumberNot Available
SMILES
O=N(=O)OCCON(=O)=O
InChI Identifier
InChI=1S/C2H4N2O6/c5-3(6)9-1-2-10-4(7)8/h1-2H2
InChI KeyUQXKXGWGFRWILX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyl nitrates. These are organic compounds containing a nitrate that is O-linked to an alkyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganic oxoanionic compounds
Sub ClassOrganic nitrates
Direct ParentAlkyl nitrates
Alternative Parents
Substituents
  • Alkyl nitrate
  • Organic nitro compound
  • Organic nitric acid or derivatives
  • Organic 1,3-dipolar compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological location
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
PropertyValueSource
logP1.17ALOGPS
logP0.64ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)-5.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area110.1 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity27.94 m³·mol⁻¹ChemAxon
Polarizability10.63 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+121.02430932474
DeepCCS[M-H]-117.77430932474
DeepCCS[M-2H]-154.64830932474
DeepCCS[M+Na]+129.68930932474
AllCCS[M+H]+132.232859911
AllCCS[M+H-H2O]+128.232859911
AllCCS[M+NH4]+135.932859911
AllCCS[M+Na]+137.032859911
AllCCS[M-H]-125.632859911
AllCCS[M+Na-2H]-127.832859911
AllCCS[M+HCOO]-130.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ethylene glycol dinitrateO=N(=O)OCCON(=O)=O1853.7Standard polar33892256
Ethylene glycol dinitrateO=N(=O)OCCON(=O)=O973.9Standard non polar33892256
Ethylene glycol dinitrateO=N(=O)OCCON(=O)=O1017.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ethylene glycol dinitrate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gw4-9200000000-98a77c62ea99dd924cb92021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethylene glycol dinitrate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylene glycol dinitrate 10V, Positive-QTOFsplash10-0udi-5900000000-b60a13315438ab981e482019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylene glycol dinitrate 20V, Positive-QTOFsplash10-0gvo-9200000000-ec4d5413a19bc49275802019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylene glycol dinitrate 40V, Positive-QTOFsplash10-004i-9000000000-1977e5db53f5a7c231e52019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylene glycol dinitrate 10V, Negative-QTOFsplash10-0udi-0900000000-d4ac15b2ed66b731cdd32019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylene glycol dinitrate 20V, Negative-QTOFsplash10-0udi-3900000000-9acb3d443a5bc70683ca2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethylene glycol dinitrate 40V, Negative-QTOFsplash10-0udi-4900000000-2c1e0125df8a93e2a6852019-02-23Wishart LabView Spectrum
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 IDNot Available
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 LinkNot Available
METLIN IDNot Available
PubChem Compound40818
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 ]