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Showing metabocard for Hydroxylamine (HMDB0003338)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-12 19:06:36 UTC
Update Date2023-02-21 17:16:36 UTC
HMDB IDHMDB0003338
Secondary Accession Numbers
  • HMDB0060880
  • HMDB03338
  • HMDB60880
Metabolite Identification
Common NameHydroxylamine
DescriptionHydroxylamine is a reactive chemical with formula NH2OH. It can be considered a hybrid of ammonia and water due to parallels it shares with each. At room temperature pure NH2OH is ordinarily a white, unstable crystalline, hygroscopic compound; however it is almost always encountered as an aqueous solution. A colorless inorganic compound (HONH2) used in organic synthesis and as a reducing agent, due to its ability to donate nitric oxide. Hydroxylamine may explode on heating. It is an irritant to the respiratory tract, skin, eyes, and other mucous membranes. It may be absorbed through the skin, is harmful if swallowed, and is a possible mutagen. NH2OH is an intermediate in the biological nitrification. The oxidation of NH3 is mediated by HAO (hydroxylamine oxidoreductase).
Structure
Data?1676999796
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0003338 (Hydroxylamine)


  Mrv0541 02231219422D          

  2  1  0  0  0  0            999 V2000
   18.9773   -6.2045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2629   -6.6170    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
M  END
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3D MOL for HMDB0003338 (Hydroxylamine)

HMDB0003338
     RDKit          3D
Hydroxylamine
  5  4  0  0  0  0  0  0  0  0999 V2000
   -0.4010    0.0222   -0.2089 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7822   -0.2626    0.3599 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0321   -0.7780   -0.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8316    0.9022    0.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4826    0.1161   -0.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  1  4  1  0
  2  5  1  0
M  END
Download

3D SDF for HMDB0003338 (Hydroxylamine)


  Mrv0541 02231219422D          

  2  1  0  0  0  0            999 V2000
   18.9773   -6.2045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2629   -6.6170    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003338

> <DATABASE_NAME>
hmdb

> <SMILES>
NO

> <INCHI_IDENTIFIER>
InChI=1S/H3NO/c1-2/h2H,1H2

> <INCHI_KEY>
AVXURJPOCDRRFD-UHFFFAOYSA-N

> <FORMULA>
H3NO

> <MOLECULAR_WEIGHT>
33.0299

> <EXACT_MASS>
33.021463723

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
2.7762143657830944

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
hydroxylamine

> <JCHEM_LOGP>
-0.7404963796666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.646080927540282

> <JCHEM_PKA_STRONGEST_BASIC>
3.9363259098959786

> <JCHEM_POLAR_SURFACE_AREA>
46.25

> <JCHEM_REFRACTIVITY>
7.848700000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
hydroxylamine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0003338 (Hydroxylamine)

HMDB0003338
     RDKit          3D
Hydroxylamine
  5  4  0  0  0  0  0  0  0  0999 V2000
   -0.4010    0.0222   -0.2089 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7822   -0.2626    0.3599 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0321   -0.7780   -0.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8316    0.9022    0.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4826    0.1161   -0.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  1  4  1  0
  2  5  1  0
M  END
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PDB for HMDB0003338 (Hydroxylamine)

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  O   UNK     0      35.424 -11.582   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0      34.091 -12.352   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1                                                            
MASTER        0    0    0    0    0    0    0    0    2    0    2    0
END
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3D PDB for HMDB0003338 (Hydroxylamine)

COMPND    HMDB0003338
HETATM    1  N1  UNL     1      -0.401   0.022  -0.209  1.00  0.00           N  
HETATM    2  O1  UNL     1       0.782  -0.263   0.360  1.00  0.00           O  
HETATM    3  H1  UNL     1      -1.032  -0.778  -0.042  1.00  0.00           H  
HETATM    4  H2  UNL     1      -0.832   0.902   0.110  1.00  0.00           H  
HETATM    5  H3  UNL     1       1.483   0.116  -0.219  1.00  0.00           H  
CONECT    1    2    3    4
CONECT    2    5
END
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SMILES for HMDB0003338 (Hydroxylamine)

NO
Download

INCHI for HMDB0003338 (Hydroxylamine)

InChI=1S/H3NO/c1-2/h2H,1H2
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View in JSmolView Stereo Labels
Synonyms
ValueSource
[NH2OH]ChEBI
H2NHOChEBI
HYDROXYAMINEChEBI
HydroxylaminChEBI
OxyammoniaChEBI
NH2OHKegg
Hydroxylamine hydrochlorideMeSH
Hydroxylammonium chlorideMeSH
(1) HydroxylamineHMDB
DihydridohydroxidonitrogenHMDB
Hydroxyamine hydrochlorideHMDB
Hydroxylamine chlorideHMDB
Hydroxylamine-1-hydrochlorideHMDB
NitroxideHMDB
OxammoniumHMDB
Oxammonium hydrochlorideHMDB
Chloride, hydroxylammoniumMeSH, HMDB
Hydrochloride, hydroxylamineMeSH, HMDB
Chemical FormulaH3NO
Average Molecular Weight33.0299
Monoisotopic Molecular Weight33.021463723
IUPAC Namehydroxylamine
Traditional Namehydroxylamine
CAS Registry Number7803-49-8
SMILES
NO
InChI Identifier
InChI=1S/H3NO/c1-2/h2H,1H2
InChI KeyAVXURJPOCDRRFD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of inorganic compounds known as homogeneous other non-metal compounds. These are inorganic non-metallic compounds in which the largest atom belongs to the class of 'other non-metals'.
KingdomInorganic compounds
Super ClassHomogeneous non-metal compounds
ClassHomogeneous other non-metal compounds
Sub ClassNot Available
Direct ParentHomogeneous other non-metal compounds
Alternative ParentsNot Available
Substituents
  • Homogeneous other non metal
Molecular FrameworkNot Available
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Biological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point33 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP-0.74ChemAxon
pKa (Strongest Acidic)17.65ChemAxon
pKa (Strongest Basic)3.94ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area46.25 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity7.85 m³·mol⁻¹ChemAxon
Polarizability2.78 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]+111.69830932474
DeepCCS[M-H]-109.90330932474
DeepCCS[M-2H]-145.09930932474
DeepCCS[M+Na]+118.56430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
HydroxylamineNO1330.5Standard polar33892256
HydroxylamineNO569.5Standard non polar33892256
HydroxylamineNO590.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Hydroxylamine,1TMS,isomer #1C[Si](C)(C)NO725.9Semi standard non polar33892256
Hydroxylamine,1TMS,isomer #1C[Si](C)(C)NO763.8Standard non polar33892256
Hydroxylamine,1TMS,isomer #1C[Si](C)(C)NO1108.8Standard polar33892256
Hydroxylamine,2TMS,isomer #1C[Si](C)(C)N(O)[Si](C)(C)C927.3Semi standard non polar33892256
Hydroxylamine,2TMS,isomer #1C[Si](C)(C)N(O)[Si](C)(C)C923.4Standard non polar33892256
Hydroxylamine,2TMS,isomer #1C[Si](C)(C)N(O)[Si](C)(C)C1089.0Standard polar33892256
Hydroxylamine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NO963.0Semi standard non polar33892256
Hydroxylamine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NO944.6Standard non polar33892256
Hydroxylamine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NO1213.6Standard polar33892256
Hydroxylamine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(O)[Si](C)(C)C(C)(C)C1329.1Semi standard non polar33892256
Hydroxylamine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(O)[Si](C)(C)C(C)(C)C1298.2Standard non polar33892256
Hydroxylamine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(O)[Si](C)(C)C(C)(C)C1307.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Hydroxylamine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9800000000-40500c2ce42330f68e232014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Hydroxylamine GC-MS (3 TMS)splash10-001j-1900000000-380d2510f339c8852cae2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Hydroxylamine GC-EI-TOF (Non-derivatized)splash10-00di-9800000000-40500c2ce42330f68e232017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Hydroxylamine GC-MS (Non-derivatized)splash10-001j-1900000000-380d2510f339c8852cae2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Hydroxylamine GC-EI-TOF (Non-derivatized)splash10-00m1-1900000000-7c1a1a9c2955e5f4d75e2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxylamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-6a1320306a7bbc43c2582017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxylamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxylamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxylamine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-001i-9000000000-17862dd274dc5ae95e9b2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxylamine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-001i-9000000000-c7d671f97d82bbe3e4582012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxylamine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-001i-9000000000-36b50bedfc3b86b95fdf2012-07-25HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxylamine 10V, Positive-QTOFsplash10-001i-9000000000-190eddac91b76eed90652017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxylamine 20V, Positive-QTOFsplash10-001i-9000000000-190eddac91b76eed90652017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxylamine 40V, Positive-QTOFsplash10-001i-9000000000-190eddac91b76eed90652017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxylamine 10V, Negative-QTOFsplash10-001i-9000000000-20928e005423160892f32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxylamine 20V, Negative-QTOFsplash10-001i-9000000000-20928e005423160892f32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxylamine 40V, Negative-QTOFsplash10-001i-9000000000-20928e005423160892f32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxylamine 10V, Positive-QTOFsplash10-001i-9000000000-190eddac91b76eed90652021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxylamine 20V, Positive-QTOFsplash10-001i-9000000000-190eddac91b76eed90652021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxylamine 40V, Positive-QTOFsplash10-001i-9000000000-190eddac91b76eed90652021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxylamine 10V, Negative-QTOFsplash10-001i-9000000000-6c136ec6f9ff4bb554452021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxylamine 20V, Negative-QTOFsplash10-001i-9000000000-6c136ec6f9ff4bb554452021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxylamine 40V, Negative-QTOFsplash10-001i-9000000000-6c136ec6f9ff4bb554452021-09-23Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Epidermis
  • Fibroblasts
  • Kidney
  • Liver
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
 details
UrineDetected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB007499
KNApSAcK IDC00053330
Chemspider ID766
KEGG Compound IDC00192
BioCyc IDHYDROXYLAMINE
BiGG IDNot Available
Wikipedia LinkHydroxylamine
METLIN ID6894
PubChem Compound787
PDB IDNot Available
ChEBI ID15429
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Lin J, Cashman JR: Detoxication of tyramine by the flavin-containing monooxygenase: stereoselective formation of the trans oxime. Chem Res Toxicol. 1997 Aug;10(8):842-52. [PubMed:9282832 ]
  2. Yang X, Arosio P, Chasteen ND: Molecular diffusion into ferritin: pathways, temperature dependence, incubation time, and concentration effects. Biophys J. 2000 Apr;78(4):2049-59. [PubMed:10733983 ]
  3. Atamna H, Robinson C, Ingersoll R, Elliott H, Ames BN: N-t-Butyl hydroxylamine is an antioxidant that reverses age-related changes in mitochondria in vivo and in vitro. FASEB J. 2001 Oct;15(12):2196-204. [PubMed:11641246 ]
  4. Cribb AE, Spielberg SP: Sulfamethoxazole is metabolized to the hydroxylamine in humans. Clin Pharmacol Ther. 1992 May;51(5):522-6. [PubMed:1587066 ]
  5. Alonso A, Meirelles NC, Tabak M: Stratum corneum intercellular lipid as compared to erythrocyte ghosts: an ESR study of thermotropic behavior and nitroxide reduction. Electron Spin Resonance. Physiol Chem Phys Med NMR. 1995;27(1):63-72. [PubMed:7617746 ]
  6. Fuchs J, Freisleben HJ, Podda M, Zimmer G, Milbradt R, Packer L: Nitroxide radical biostability in skin. Free Radic Biol Med. 1993 Oct;15(4):415-23. [PubMed:8225023 ]
  7. Kurian JR, Bajad SU, Miller JL, Chin NA, Trepanier LA: NADH cytochrome b5 reductase and cytochrome b5 catalyze the microsomal reduction of xenobiotic hydroxylamines and amidoximes in humans. J Pharmacol Exp Ther. 2004 Dec;311(3):1171-8. Epub 2004 Aug 9. [PubMed:15302896 ]
  8. Coleman MD, Jacobus DP: Reduction of dapsone hydroxylamine to dapsone during methaemoglobin formation in human erythrocytes in vitro--II. Movement of dapsone across a semipermeable membrane into erythrocytes and plasma. Biochem Pharmacol. 1993 Oct 19;46(8):1363-8. [PubMed:8240384 ]
  9. Peng SX, Strojnowski MJ, Hu JK, Smith BJ, Eichhold TH, Wehmeyer KR, Pikul S, Almstead NG: Gas chromatographic-mass spectrometric analysis of hydroxylamine for monitoring the metabolic hydrolysis of metalloprotease inhibitors in rat and human liver microsomes. J Chromatogr B Biomed Sci Appl. 1999 Mar 5;724(1):181-7. [PubMed:10202971 ]
  10. Forsyth NR, Evans AP, Shay JW, Wright WE: Developmental differences in the immortalization of lung fibroblasts by telomerase. Aging Cell. 2003 Oct;2(5):235-43. [PubMed:14570231 ]
  11. Goda R, Nagai D, Akiyama Y, Nishikawa K, Ikemoto I, Aizawa Y, Nagata K, Yamazoe Y: Detection of a new N-oxidized metabolite of flutamide, N-[4-nitro-3-(trifluoromethyl)phenyl]hydroxylamine, in human liver microsomes and urine of prostate cancer patients. Drug Metab Dispos. 2006 May;34(5):828-35. Epub 2006 Feb 28. [PubMed:16507648 ]
  12. Winter HR, Unadkat JD: Identification of cytochrome P450 and arylamine N-acetyltransferase isoforms involved in sulfadiazine metabolism. Drug Metab Dispos. 2005 Jul;33(7):969-76. Epub 2005 Apr 20. [PubMed:15843491 ]
  13. Coleman MD: Dapsone: modes of action, toxicity and possible strategies for increasing patient tolerance. Br J Dermatol. 1993 Nov;129(5):507-13. [PubMed:8251346 ]