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Showing metabocard for Vaporole (HMDB0001382)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:39 UTC
HMDB IDHMDB0001382
Secondary Accession Numbers
  • HMDB01382
Metabolite Identification
Common NameVaporole
DescriptionIsoamyl nitrite (IAN) has been used as antianginal agents for more than 100 years. It is now established that IAN cause direct vasorelaxation through vascular generation of NO and relaxation via a cyclic guanosine monophosphate-dependent process. (PMID: 8996213 ). IAN is a member of the family of volatile organic nitrites that exert vasodilatory effects and have recently exhibited a considerable potential for inhalation abuse. (PMID: 9829558 ). All nitrovasodilators act intracellularly by a common molecular mechanism. This is characterized by the release of nitric oxide (NO). This process basically depends on the presence of oxygen as electron acceptor from the sydnonimine molecule. Organic nitrites (such as IAN) require the interaction with a mercapto group to form a S-nitrosothiol intermediate, from which finally NO radicals are liberated. In the presence of thiol compounds organic nitrites (e.g., IAN) and nitrosothiols may act as intermediary products of NO generation. (PMID: 1683227 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001382 (Vaporole)

  Mrv0541 02231219062D          

  8  7  0  0  0  0            999 V2000
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   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    0.4125    0.0000 N   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
  5  6  1  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  7  8  2  0  0  0  0
  4  5  1  0  0  0  0
  2  4  1  0  0  0  0
  6  7  1  0  0  0  0
M  END
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3D MOL for HMDB0001382 (Vaporole)

HMDB0001382
     RDKit          3D
Vaporole
 19 18  0  0  0  0  0  0  0  0999 V2000
   -1.8781    1.3055   -0.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7131    0.5965    0.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1837   -0.8082    0.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3937    0.5333   -0.7342 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6266   -0.1492   -0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4002   -1.4663    0.1824 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4590   -2.1897    0.6771 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4592   -1.6159    1.1935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4906    2.1303   -0.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3629    0.5723   -1.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6075    1.6935    0.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4179    1.0625    1.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5646   -1.2216    1.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0081   -1.4038   -0.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2657   -0.7852    0.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6658    1.5353   -1.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0193   -0.0602   -1.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3984   -0.1194   -1.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0702    0.3901    0.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  3 13  1  0
  3 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
M  END
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3D SDF for HMDB0001382 (Vaporole)

  Mrv0541 02231219062D          

  8  7  0  0  0  0            999 V2000
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   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    0.4125    0.0000 N   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
  5  6  1  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  7  8  2  0  0  0  0
  4  5  1  0  0  0  0
  2  4  1  0  0  0  0
  6  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001382

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CCON=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H11NO2/c1-5(2)3-4-8-6-7/h5H,3-4H2,1-2H3

> <INCHI_KEY>
OWFXIOWLTKNBAP-UHFFFAOYSA-N

> <FORMULA>
C5H11NO2

> <MOLECULAR_WEIGHT>
117.1463

> <EXACT_MASS>
117.078978601

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
12.626389799422277

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-methylbutyl nitrite

> <ALOGPS_LOGP>
1.87

> <JCHEM_LOGP>
2.155016471666667

> <ALOGPS_LOGS>
-1.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8146089433815895

> <JCHEM_POLAR_SURFACE_AREA>
38.66

> <JCHEM_REFRACTIVITY>
31.626200000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.88e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aspiral

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0001382 (Vaporole)

HMDB0001382
     RDKit          3D
Vaporole
 19 18  0  0  0  0  0  0  0  0999 V2000
   -1.8781    1.3055   -0.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7131    0.5965    0.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1837   -0.8082    0.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3937    0.5333   -0.7342 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6266   -0.1492   -0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4002   -1.4663    0.1824 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4590   -2.1897    0.6771 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4592   -1.6159    1.1935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4906    2.1303   -0.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3629    0.5723   -1.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6075    1.6935    0.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4179    1.0625    1.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5646   -1.2216    1.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0081   -1.4038   -0.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2657   -0.7852    0.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6658    1.5353   -1.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0193   -0.0602   -1.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3984   -0.1194   -1.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0702    0.3901    0.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  3 13  1  0
  3 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
M  END
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PDB for HMDB0001382 (Vaporole)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       1.334   0.770   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    5    2                                                       
CONECT    5    6    4                                                       
CONECT    6    5    7                                                       
CONECT    7    8    6                                                       
CONECT    8    7                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for HMDB0001382 (Vaporole)

COMPND    HMDB0001382
HETATM    1  C1  UNL     1      -1.878   1.305  -0.378  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.713   0.596   0.288  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.184  -0.808   0.604  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.394   0.533  -0.734  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.627  -0.149  -0.212  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.400  -1.466   0.182  1.00  0.00           O  
HETATM    7  N1  UNL     1       2.459  -2.190   0.677  1.00  0.00           N  
HETATM    8  O2  UNL     1       3.459  -1.616   1.193  1.00  0.00           O  
HETATM    9  H1  UNL     1      -1.491   2.130  -0.989  1.00  0.00           H  
HETATM   10  H2  UNL     1      -2.363   0.572  -1.069  1.00  0.00           H  
HETATM   11  H3  UNL     1      -2.607   1.694   0.359  1.00  0.00           H  
HETATM   12  H4  UNL     1      -0.418   1.063   1.232  1.00  0.00           H  
HETATM   13  H5  UNL     1      -0.565  -1.222   1.437  1.00  0.00           H  
HETATM   14  H6  UNL     1      -1.008  -1.404  -0.329  1.00  0.00           H  
HETATM   15  H7  UNL     1      -2.266  -0.785   0.871  1.00  0.00           H  
HETATM   16  H8  UNL     1       0.666   1.535  -1.121  1.00  0.00           H  
HETATM   17  H9  UNL     1       0.019  -0.060  -1.586  1.00  0.00           H  
HETATM   18  H10 UNL     1       2.398  -0.119  -1.008  1.00  0.00           H  
HETATM   19  H11 UNL     1       2.070   0.390   0.662  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    4   12
CONECT    3   13   14   15
CONECT    4    5   16   17
CONECT    5    6   18   19
CONECT    6    7
CONECT    7    8    8
END
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SMILES for HMDB0001382 (Vaporole)

CC(C)CCON=O
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INCHI for HMDB0001382 (Vaporole)

InChI=1S/C5H11NO2/c1-5(2)3-4-8-6-7/h5H,3-4H2,1-2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC5H11NO2
Average Molecular Weight117.1463
Monoisotopic Molecular Weight117.078978601
IUPAC Name3-methylbutyl nitrite
Traditional Nameaspiral
CAS Registry Number110-46-3
SMILES
CC(C)CCON=O
InChI Identifier
InChI=1S/C5H11NO2/c1-5(2)3-4-8-6-7/h5H,3-4H2,1-2H3
InChI KeyOWFXIOWLTKNBAP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organic o-nitroso compounds. These are organic compounds containing a n-nitroso group -ON=O.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassOrganic nitroso compounds
Direct ParentOrganic O-nitroso compounds
Alternative Parents
Substituents
  • Organic o-nitroso compound
  • Alkyl nitrite
  • Organic nitrite
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point99.2 °CNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022593
KNApSAcK IDNot Available
Chemspider ID7762
KEGG Compound IDC07457
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVaporole
METLIN IDNot Available
PubChem Compound8053
PDB IDNot Available
ChEBI ID2691
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceWilson, S. D.; Yang, E. F. Preparation of the pure isomers of amyl nitrite. Zhongguo Shenglixue Zazhi (1930), 4 391-2.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bauer JA, Nolan T, Fung HL: Vascular and hemodynamic differences between organic nitrates and nitrites. J Pharmacol Exp Ther. 1997 Jan;280(1):326-31. [PubMed:8996213 ]
  2. Ramanathan VM, Reigle TG, Muralidhara S, Dallas CE: Effects of acute inhalation exposure to isoamyl nitrite on the hypothalamo-pituitary-adrenal axis in male Sprague-Dawley rats. J Toxicol Environ Health A. 1998 Nov 13;55(5):345-58. [PubMed:9829558 ]
  3. Noack E, Feelisch M: Molecular mechanisms of nitrovasodilator bioactivation. Basic Res Cardiol. 1991;86 Suppl 2:37-50. [PubMed:1683227 ]