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Record Information
Version3.6
Creation Date2012-09-06 15:16:50 UTC
Update Date2016-02-11 01:29:32 UTC
HMDB IDHMDB14691
Secondary Accession NumbersNone
Metabolite Identification
Common NameAcetohydroxamic Acid
DescriptionAcetohydroxamic Acid, a synthetic drug derived from hydroxylamine and ethyl acetate, is similar in structure to urea. In the urine, it acts as an antagonist of the bacterial enzyme urease. Acetohydroxamic Acid has no direct antimicrobial action and does not acidify urine directly. It is used, in addition to antibiotics or medical procedures, to treat chronic urea-splitting urinary infections.
Structure
Thumb
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
AcetohydroxamateGenerator
Acetate, oximeGenerator
AcetylhydroxamateGenerator
CetohyroxamateGenerator
MethylhydroxamateGenerator
Acetohydroximic acidHMDB
Acetyl hydroxyaminoHMDB
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 KeyInChIKey=RRUDCFGSUDOHDG-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Enzyme Inhibitors
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point90.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.09e+02 g/LNot Available
LogP-0.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility509.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity16.23 m3·mol-1ChemAxon
Polarizability6.6 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00551
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00551
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00551
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID1913
KEGG Compound IDC06808
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcetohydroxamic_acid
NuGOwiki LinkHMDB14691
Metagene LinkHMDB14691
METLIN IDNot Available
PubChem Compound1990
PDB IDHAE
ChEBI ID27777
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. [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. [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. [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. [16959356 ]