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Showing metabocard for Acetohydroxamic Acid (HMDB0014691)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2023-02-21 17:18:15 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).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0014691 (Acetohydroxamic Acid)

  Mrv0541 02231214462D          

  5  4  0  0  0  0            999 V2000
    2.0930    0.0495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.8745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.3630    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  2  4  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
M  END
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3D MOL for HMDB0014691 (Acetohydroxamic Acid)

HMDB0014691
     RDKit          3D
Acetohydroxamic Acid
 10  9  0  0  0  0  0  0  0  0999 V2000
   -1.4685    0.0778   -0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1970   -0.1982    0.4909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4110   -0.7932    1.5696 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0200    0.2270   -0.0563 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0994    0.6041   -0.5416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1836    0.4811    0.4913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2921    0.8300   -1.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8378   -0.8853   -0.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6767   -0.2169    1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5938   -0.1264   -1.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  4  9  1  0
  5 10  1  0
M  END
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3D SDF for HMDB0014691 (Acetohydroxamic Acid)

  Mrv0541 02231214462D          

  5  4  0  0  0  0            999 V2000
    2.0930    0.0495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.8745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.3630    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  2  4  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014691

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)NO

> <INCHI_IDENTIFIER>
InChI=1S/C2H5NO2/c1-2(4)3-5/h5H,1H3,(H,3,4)

> <INCHI_KEY>
RRUDCFGSUDOHDG-UHFFFAOYSA-N

> <FORMULA>
C2H5NO2

> <MOLECULAR_WEIGHT>
75.0666

> <EXACT_MASS>
75.032028409

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
6.603745685886922

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-hydroxyacetamide

> <ALOGPS_LOGP>
-1.46

> <JCHEM_LOGP>
-1.0334700553333331

> <ALOGPS_LOGS>
0.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.377702380221294

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.943521799436219

> <JCHEM_PKA_STRONGEST_BASIC>
-5.447093399828362

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
16.2305

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.09e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetohydroxamic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0014691 (Acetohydroxamic Acid)

HMDB0014691
     RDKit          3D
Acetohydroxamic Acid
 10  9  0  0  0  0  0  0  0  0999 V2000
   -1.4685    0.0778   -0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1970   -0.1982    0.4909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4110   -0.7932    1.5696 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0200    0.2270   -0.0563 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0994    0.6041   -0.5416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1836    0.4811    0.4913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2921    0.8300   -1.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8378   -0.8853   -0.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6767   -0.2169    1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5938   -0.1264   -1.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  4  9  1  0
  5 10  1  0
M  END
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PDB for HMDB0014691 (Acetohydroxamic Acid)

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       3.907   0.092   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       6.574   1.632   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       5.241  -0.678   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       6.574   0.092   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.908  -0.678   0.000  0.00  0.00           C+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    4                                                       
CONECT    4    2    3    5                                                  
CONECT    5    4                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for HMDB0014691 (Acetohydroxamic Acid)

COMPND    HMDB0014691
HETATM    1  C1  UNL     1      -1.468   0.078  -0.290  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.197  -0.198   0.491  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.411  -0.793   1.570  1.00  0.00           O  
HETATM    4  N1  UNL     1       1.020   0.227  -0.056  1.00  0.00           N  
HETATM    5  O2  UNL     1       2.099   0.604  -0.542  1.00  0.00           O  
HETATM    6  H1  UNL     1      -2.184   0.481   0.491  1.00  0.00           H  
HETATM    7  H2  UNL     1      -1.292   0.830  -1.042  1.00  0.00           H  
HETATM    8  H3  UNL     1      -1.838  -0.885  -0.622  1.00  0.00           H  
HETATM    9  H4  UNL     1       1.677  -0.217   1.025  1.00  0.00           H  
HETATM   10  H5  UNL     1       2.594  -0.126  -1.025  1.00  0.00           H  
CONECT    1    2    6    7    8
CONECT    2    3    3    4
CONECT    4    5    9
CONECT    5   10
END
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SMILES for HMDB0014691 (Acetohydroxamic Acid)

CC(=O)NO
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INCHI for HMDB0014691 (Acetohydroxamic Acid)

InChI=1S/C2H5NO2/c1-2(4)3-5/h5H,1H3,(H,3,4)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
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
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point90.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility509 g/LNot Available
LogP-0.7Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00551 details
UrineExpected but not QuantifiedNot QuantifiedNot 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
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. MedicineNet [Link]

Enzymes

Enzyme Details
1. Macrophage metalloelastase
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 ]