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Showing metabocard for Amyl Nitrite (HMDB0015550)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2023-02-21 17:18:32 UTC
HMDB IDHMDB0015550
Secondary Accession Numbers
  • HMDB15550
Metabolite Identification
Common NameAmyl Nitrite
DescriptionAmyl Nitrite, also known as pentyl nitrite or 1-nitropentane, 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 n-pentyl as the alkyl group. Amyl Nitrite is a drug which is used for the rapid relief of angina pectoris. Amyl Nitrite is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0015550 (Amyl Nitrite)

  Mrv0541 04191212182D          

  8  7  0  0  0  0            999 V2000
   -1.4289    0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.2357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  1  1  0  0  0  0
  4  3  1  0  0  0  0
  6  5  2  0  0  0  0
  3  7  1  0  0  0  0
  7  5  1  0  0  0  0
  2  8  1  0  0  0  0
M  END
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3D MOL for HMDB0015550 (Amyl Nitrite)

HMDB0015550
     RDKit          3D
Amyl Nitrite
 19 18  0  0  0  0  0  0  0  0999 V2000
   -2.8819    0.2995    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4665    0.8604    0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5539   -0.3493    0.1920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8418    0.1440    0.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7491   -0.9244    0.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8187   -1.0333   -0.1959 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6395    0.0628   -0.2691 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1912    0.4596    0.7566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9161   -0.4082   -0.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9853   -0.3102    0.9393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6439    1.0780   -0.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3329    1.5419    0.9212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2204    1.3311   -0.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8160   -0.8877    1.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8059   -0.9546   -0.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0996    0.3321   -0.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9338    1.1140    0.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2101   -1.8566    0.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1392   -0.4992    1.6821 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  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
  2 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 HMDB0015550 (Amyl Nitrite)

  Mrv0541 04191212182D          

  8  7  0  0  0  0            999 V2000
   -1.4289    0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.2357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  1  1  0  0  0  0
  4  3  1  0  0  0  0
  6  5  2  0  0  0  0
  3  7  1  0  0  0  0
  7  5  1  0  0  0  0
  2  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015550

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCON=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H11NO2/c1-2-3-4-5-8-6-7/h2-5H2,1H3

> <INCHI_KEY>
CSDTZUBPSYWZDX-UHFFFAOYSA-N

> <FORMULA>
C5H11NO2

> <MOLECULAR_WEIGHT>
117.1463

> <EXACT_MASS>
117.078978601

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
12.840100937582324

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
pentyl nitrite

> <ALOGPS_LOGP>
1.98

> <JCHEM_LOGP>
2.3125660403333335

> <ALOGPS_LOGS>
-1.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8145129168936718

> <JCHEM_POLAR_SURFACE_AREA>
38.66

> <JCHEM_REFRACTIVITY>
31.678600000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.97e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
amyl nitrite

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0015550 (Amyl Nitrite)

HMDB0015550
     RDKit          3D
Amyl Nitrite
 19 18  0  0  0  0  0  0  0  0999 V2000
   -2.8819    0.2995    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4665    0.8604    0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5539   -0.3493    0.1920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8418    0.1440    0.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7491   -0.9244    0.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8187   -1.0333   -0.1959 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6395    0.0628   -0.2691 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1912    0.4596    0.7566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9161   -0.4082   -0.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9853   -0.3102    0.9393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6439    1.0780   -0.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3329    1.5419    0.9212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2204    1.3311   -0.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8160   -0.8877    1.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8059   -0.9546   -0.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0996    0.3321   -0.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9338    1.1140    0.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2101   -1.8566    0.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1392   -0.4992    1.6821 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  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
  2 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 HMDB0015550 (Amyl Nitrite)

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      -2.667   0.440   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -0.330   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.440   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -0.330   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       2.667   0.440   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0       4.001  -0.330   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.334  -0.330   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -5.335   0.440   0.000  0.00  0.00           C+0
CONECT    1    2    4                                                       
CONECT    2    1    8                                                       
CONECT    3    4    7                                                       
CONECT    4    1    3                                                       
CONECT    5    6    7                                                       
CONECT    6    5                                                            
CONECT    7    3    5                                                       
CONECT    8    2                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for HMDB0015550 (Amyl Nitrite)

COMPND    HMDB0015550
HETATM    1  C1  UNL     1      -2.882   0.300   0.037  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.467   0.860   0.033  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.554  -0.349   0.192  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.842   0.144   0.105  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.749  -0.924   0.720  1.00  0.00           C  
HETATM    6  O1  UNL     1       2.819  -1.033  -0.196  1.00  0.00           O  
HETATM    7  N1  UNL     1       3.639   0.063  -0.269  1.00  0.00           N  
HETATM    8  O2  UNL     1       4.191   0.460   0.757  1.00  0.00           O  
HETATM    9  H1  UNL     1      -2.916  -0.408  -0.838  1.00  0.00           H  
HETATM   10  H2  UNL     1      -2.985  -0.310   0.939  1.00  0.00           H  
HETATM   11  H3  UNL     1      -3.644   1.078  -0.096  1.00  0.00           H  
HETATM   12  H4  UNL     1      -1.333   1.542   0.921  1.00  0.00           H  
HETATM   13  H5  UNL     1      -1.220   1.331  -0.916  1.00  0.00           H  
HETATM   14  H6  UNL     1      -0.816  -0.888   1.082  1.00  0.00           H  
HETATM   15  H7  UNL     1      -0.806  -0.955  -0.759  1.00  0.00           H  
HETATM   16  H8  UNL     1       1.100   0.332  -0.967  1.00  0.00           H  
HETATM   17  H9  UNL     1       0.934   1.114   0.674  1.00  0.00           H  
HETATM   18  H10 UNL     1       1.210  -1.857   0.920  1.00  0.00           H  
HETATM   19  H11 UNL     1       2.139  -0.499   1.682  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3   12   13
CONECT    3    4   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 HMDB0015550 (Amyl Nitrite)

CCCCCON=O
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INCHI for HMDB0015550 (Amyl Nitrite)

InChI=1S/C5H11NO2/c1-2-3-4-5-8-6-7/h2-5H2,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
1-NitropentaneChEBI
N-Amyl nitriteChEBI
NitramylChEBI
Pentyl nitriteChEBI
Amyl nitrosumHMDB
Isoamyl nitriteHMDB
N-Pentyl nitriteHMDB
Nitrite, amylHMDB
Amyl nitriteChEBI
Chemical FormulaC5H11NO2
Average Molecular Weight117.1463
Monoisotopic Molecular Weight117.078978601
IUPAC Namepentyl nitrite
Traditional Nameamyl nitrite
CAS Registry Number463-04-7
SMILES
CCCCCON=O
InChI Identifier
InChI=1S/C5H11NO2/c1-2-3-4-5-8-6-7/h2-5H2,1H3
InChI KeyCSDTZUBPSYWZDX-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
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.97 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01612 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01612 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01612
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9632
KEGG Compound IDC07457
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAmyl nitrite
METLIN IDNot Available
PubChem Compound10026
PDB IDNot Available
ChEBI ID55344
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 ReferencesNot Available

Enzymes

Enzyme Details
1. Aldehyde dehydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
References
  1. Badejo AM Jr, Hodnette C, Dhaliwal JS, Casey DB, Pankey E, Murthy SN, Nossaman BD, Hyman AL, Kadowitz PJ: Mitochondrial aldehyde dehydrogenase mediates vasodilator responses of glyceryl trinitrate and sodium nitrite in the pulmonary vascular bed of the rat. Am J Physiol Heart Circ Physiol. 2010 Sep;299(3):H819-26. doi: 10.1152/ajpheart.00959.2009. Epub 2010 Jun 11. [PubMed:20543077 ]
Enzyme Details
2. Atrial natriuretic peptide receptor 1
General function:
Involved in phosphorus-oxygen lyase activity
Specific function:
Receptor for the atrial natriuretic peptide NPPA/ANP and the brain natriuretic peptide NPPB/BNP which are potent vasoactive hormones playing a key role in cardiovascular homeostasis. Has guanylate cyclase activity upon binding of the ligand.
Gene Name:
NPR1
Uniprot ID:
P16066
Molecular weight:
118918.11
References
  1. Madhani M, Scotland RS, MacAllister RJ, Hobbs AJ: Vascular natriuretic peptide receptor-linked particulate guanylate cyclases are modulated by nitric oxide-cyclic GMP signalling. Br J Pharmacol. 2003 Aug;139(7):1289-96. [PubMed:12890708 ]
  2. Bauersachs J: Aminoethyl nitrate--the novel super nitrate? Br J Pharmacol. 2009 Sep;158(2):507-9. doi: 10.1111/j.1476-5381.2009.00414.x. [PubMed:19732062 ]