Np mrd loader

Showing NP-Card for Vaporole (NP0049953)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version1.0
Created at2022-03-17 21:20:47 UTC
Updated at2022-03-17 21:20:47 UTC
NP-MRD IDNP0049953
Secondary Accession NumbersNone
Natural Product Identification
Common NameVaporole
DescriptionVaporole, also known as isopentyl nitrite or amyl nitrite I, belongs to the class of organic compounds known as organic o-nitroso compounds. These are organic compounds containing a n-nitroso group -ON=O. A nitrite ester having isopentyl as the alkyl group. Vaporole is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Vaporole has been detected, but not quantified in, a few different foods, such as cherry tomato, garden tomato, and garden tomato (var.). It was first documented in 1991 (PMID: 1683227). This could make vaporole a potential biomarker for the consumption of these foods (PMID: 8996213) (PMID: 9829558).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0049953 (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
Download

3D MOL for NP0049953 (Vaporole)

Download
3D SDF for NP0049953 (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>
NP0049953

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

Download
3D-SDF for NP0049953 (Vaporole)
Download
PDB for NP0049953 (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

Download
3D PDB for NP0049953 (Vaporole)
Download
SMILES for NP0049953 (Vaporole)
CC(C)CCON=O
Download
INCHI for NP0049953 (Vaporole)
InChI=1S/C5H11NO2/c1-5(2)3-4-8-6-7/h5H,3-4H2,1-2H3
Download
View in JSmol
Synonyms
ValueSource
3-Methylbutanol nitriteChEBI
3-Methylbutyl nitriteChEBI
AmilnitriteChEBI
Amyl nitrite IChEBI
Amyl nitrosumChEBI
IPNChEBI
Isopentyl nitriteChEBI
NitramylChEBI
Nitrous acid, 3-methylbutyl esterChEBI
Nitrous acid, isopentyl esterChEBI
Pentyl nitriteChEBI
Isoamyl nitriteKegg
AspiralKegg
Amyl nitritHMDB
Amyl nitrite (JP15/usp)HMDB
Amyl nitriteHMDB
Amyl nitrite(mixed isomers)HMDB
Isopentyl ester nitrous acidHMDB
Nitrite isopentyl alcoholHMDB
Nitrous acid 3-methylbutyl esterHMDB
Pentanoli nitrisHMDB
Vaporole amyl nitriteHMDB
VaporoleKEGG
Chemical FormulaC5H11NO2
Average Mass117.1463 Da
Monoisotopic Mass117.07898 Da
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
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
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
logP1.87ALOGPS
logP2.16ChemAxon
logS-1.6ALOGPS
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.66 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.63 m³·mol⁻¹ChemAxon
Polarizability12.63 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001382  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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  
Good Scents IDNot Available
References
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. doi: 10.1080/009841098158395. [PubMed:9829558  ] 
  3. Noack E, Feelisch M: Molecular mechanisms of nitrovasodilator bioactivation. Basic Res Cardiol. 1991;86 Suppl 2:37-50. doi: 10.1007/978-3-642-72461-9_5. [PubMed:1683227  ]