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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:09 UTC
HMDB IDHMDB0014691
Secondary Accession Numbers
  • HMDB14691
Metabolite Identification
Common NameAcetohydroxamic Acid
DescriptionAcetohydroxamic Acid, also known as acethydroxamsaeure or lithostat, belongs to the class of organic compounds known as acetohydroxamic acids. These are organic compounds that contain a hydroxamic acid group carrying a methyl group attached to its carbon center. Acetohydroxamic Acid is a drug which is used, in addition to antibiotics or medical procedures, to treat chronic urea-splitting urinary infections. Acetohydroxamic Acid is an extremely weak basic (essentially neutral) compound (based on its pKa). This inhibits the hydrolysis of urea and production of ammonia in urine infected with urea-splitting organisms, leading to a decrease in pH and ammonia levels. In the urine, it acts as an antagonist of the bacterial enzyme urease. Symptoms of overdose include anorexia, malaise, lethargy, diminished sense of wellbeing, tremor, anxiety, nausea, and vomiting.
Structure
Data?1582753209
Synonyms
ValueSource
AcethydroxamsaeureChEBI
AcethydroxamsaureChEBI
Acetic acid, oximeChEBI
Acetylhydroxamic acidChEBI
Acide acetohydroxamiqueChEBI
Acido acetohidroxamicoChEBI
Acidum acetohydroxamicumChEBI
AHAChEBI
Cetohyroxamic acidChEBI
LithostatChEBI
Methylhydroxamic acidChEBI
N-Acetyl hydroxyacetamideChEBI
N-AcetylhydroxylamineChEBI
N-HydroxyacetamideChEBI
Acetate, oximeGenerator
AcetylhydroxamateGenerator
CetohyroxamateGenerator
MethylhydroxamateGenerator
AcetohydroxamateGenerator
Acetohydroximic acidHMDB
Acetyl hydroxyaminoHMDB
Mission brand OF acetohydroxamic acidHMDB
N-HydroxyacetamidineHMDB
Robert brand OF acetohydroxamic acidHMDB
UronefrexHMDB
Chemical FormulaC2H5NO2
Average Molecular Weight75.0666
Monoisotopic Molecular Weight75.032028409
IUPAC NameN-hydroxyacetamide
Traditional Nameacetohydroxamic acid
CAS Registry Number546-88-3
SMILES
CC(=O)NO
InChI Identifier
InChI=1S/C2H5NO2/c1-2(4)3-5/h5H,1H3,(H,3,4)
InChI KeyRRUDCFGSUDOHDG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as acetohydroxamic acids. These are organic compounds that contain a hydroxamic acid group carrying a methyl group attached to its carbon center.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentAcetohydroxamic acids
Alternative Parents
Substituents
  • Acetohydroxamic acid
  • Acetamide
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point90.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility509 g/LNot Available
LogP-0.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility509 g/LALOGPS
logP-1.5ALOGPS
logP-1ChemAxon
logS0.83ALOGPS
pKa (Strongest Acidic)8.94ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity16.23 m³·mol⁻¹ChemAxon
Polarizability6.6 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-09c5ca2b46a7bf5a4209Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-384a9326901e6005b71dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-9000000000-7336fad23ac851740fc3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-0400282accbe476c1f6bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-019e675cb517b6e5664bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-f0f196a2ff31d0228eb2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-03a2ee31082bb56150e6Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00551 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00551 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00551
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID1913
KEGG Compound IDC06808
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcetohydroxamic_Acid
METLIN IDNot Available
PubChem Compound1990
PDB IDHAE
ChEBI ID27777
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. MedicineNet [Link]

Enzymes

General function:
Involved in metalloendopeptidase activity
Specific function:
May be involved in tissue injury and remodeling. Has significant elastolytic activity. Can accept large and small amino acids at the P1' site, but has a preference for leucine. Aromatic or hydrophobic residues are preferred at the P1 site, with small hydrophobic residues (preferably alanine) occupying P3
Gene Name:
MMP12
Uniprot ID:
P39900
Molecular weight:
54001.2
References
  1. Mannino C, Nievo M, Machetti F, Papakyriakou A, Calderone V, Fragai M, Guarna A: Synthesis of bicyclic molecular scaffolds (BTAa): an investigation towards new selective MMP-12 inhibitors. Bioorg Med Chem. 2006 Nov 15;14(22):7392-403. Epub 2006 Aug 8. [PubMed:16899369 ]
  2. Bertini I, Calderone V, Cosenza M, Fragai M, Lee YM, Luchinat C, Mangani S, Terni B, Turano P: Conformational variability of matrix metalloproteinases: beyond a single 3D structure. Proc Natl Acad Sci U S A. 2005 Apr 12;102(15):5334-9. Epub 2005 Apr 4. [PubMed:15809432 ]
  3. Bertini I, Calderone V, Fragai M, Giachetti A, Loconte M, Luchinat C, Maletta M, Nativi C, Yeo KJ: Exploring the subtleties of drug-receptor interactions: the case of matrix metalloproteinases. J Am Chem Soc. 2007 Mar 7;129(9):2466-75. Epub 2007 Feb 2. [PubMed:17269766 ]
  4. Fukuda M, Peppas NA, McGinity JW: Floating hot-melt extruded tablets for gastroretentive controlled drug release system. J Control Release. 2006 Oct 10;115(2):121-9. Epub 2006 Jul 21. [PubMed:16959356 ]