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Showing metabocard for 5-Acetamidovalerate (HMDB0012175)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2009-04-06 16:20:29 UTC
Update Date2023-02-21 17:17:42 UTC
HMDB IDHMDB0012175
Secondary Accession Numbers
  • HMDB12175
Metabolite Identification
Common Name5-Acetamidovalerate
Description5-Acetamidovalerate is involved in the lysine degradation III pathway. It can be generated from the enzymatic reduction of 5-aminopentanoate or enzymatic oxidation of 2-keto-6-acetamidocaproate. Experiment using DL-{4,5-3H}lysine showed 5-acetamidovalerate as the major product. If radiolabeled N6-acetyl-L-lysine was used with added α-ketoglutarate, and pyridoxal phosphate, radiolabeled 2-keto-6-acetamidocaproate was produced. α-Ketoglutarate was preferred over pyruvate, and there was little or no dependence on pyridoxal phosphate. If thiamine pyrophosphate and NAD were added to a similar reaction, virtually all of the label was in 5-acetamidovalerate. If labeled 5-acetamidovalerate was used, labeled 5-aminovalerate (5-aminopentanoate) was identified. In addition, whole cell cultures of R. leguminicola incubated with labeled 5-acetamidovalerate accumulated radiolabeled glutarate. Whole cell cultures incubated with radiolabeled glutarate produced a mixture of tricarboxylic acid cycle acids and other carboxylic acids.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0012175 (5-Acetamidovalerate)

  Mrv0541 02241203482D          

 11 10  0  0  0  0            999 V2000
   11.9908   -5.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5631   -5.9758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8486   -5.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2776   -5.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1342   -5.9758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7052   -5.9758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9921   -5.9758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4197   -5.5633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7052   -6.8009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9921   -6.8009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7066   -5.5633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  9  2  0  0  0  0
  6  8  1  0  0  0  0
  7 10  1  0  0  0  0
  7 11  2  0  0  0  0
M  END
Download

3D MOL for HMDB0012175 (5-Acetamidovalerate)

HMDB0012175
     RDKit          3D
5-Acetamidovalerate
 24 23  0  0  0  0  0  0  0  0999 V2000
    0.9506    3.5758    1.4680 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8186    2.4346    0.8283 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8778    2.8769    0.4012 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2366    1.2355    0.8829 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6286   -0.0206    0.9392 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2982   -0.6506   -0.3579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4915   -1.9283   -0.1492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9551   -2.5355   -1.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8331   -1.5690   -2.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8162   -1.3687   -3.3869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7325   -0.8365   -1.4106 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4607    4.4970    1.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0033    3.5713    0.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8055    3.1748    2.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2502    0.6553    0.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3213    0.1247    1.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3038   -0.6759    1.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3283   -0.9892   -0.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1184    0.0440   -1.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3979   -1.7304    0.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1288   -2.6709    0.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6084   -3.4221   -1.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0940   -2.8850   -2.0401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7158   -0.9072   -1.5864 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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  6 19  1  0
  7 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
 11 24  1  0
M  END
Download

3D SDF for HMDB0012175 (5-Acetamidovalerate)

  Mrv0541 02241203482D          

 11 10  0  0  0  0            999 V2000
   11.9908   -5.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5631   -5.9758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8486   -5.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2776   -5.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1342   -5.9758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7052   -5.9758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9921   -5.9758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4197   -5.5633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7052   -6.8009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9921   -6.8009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7066   -5.5633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  9  2  0  0  0  0
  6  8  1  0  0  0  0
  7 10  1  0  0  0  0
  7 11  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012175

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)NCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H13NO3/c1-6(9)8-5-3-2-4-7(10)11/h2-5H2,1H3,(H,8,9)(H,10,11)

> <INCHI_KEY>
TZZSWAXSIGWXOS-UHFFFAOYSA-N

> <FORMULA>
C7H13NO3

> <MOLECULAR_WEIGHT>
159.183

> <EXACT_MASS>
159.089543287

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
16.882839501527194

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-acetamidopentanoic acid

> <ALOGPS_LOGP>
-0.07

> <JCHEM_LOGP>
-0.35838634766666655

> <ALOGPS_LOGS>
-1.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.936010347023988

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.591615336812979

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6273255306025484

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
39.5026

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.38e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-acetamidopentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0012175 (5-Acetamidovalerate)

HMDB0012175
     RDKit          3D
5-Acetamidovalerate
 24 23  0  0  0  0  0  0  0  0999 V2000
    0.9506    3.5758    1.4680 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8186    2.4346    0.8283 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8778    2.8769    0.4012 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2366    1.2355    0.8829 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6286   -0.0206    0.9392 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2982   -0.6506   -0.3579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4915   -1.9283   -0.1492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9551   -2.5355   -1.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8331   -1.5690   -2.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8162   -1.3687   -3.3869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7325   -0.8365   -1.4106 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4607    4.4970    1.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0033    3.5713    0.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8055    3.1748    2.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2502    0.6553    0.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3213    0.1247    1.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3038   -0.6759    1.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3283   -0.9892   -0.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1184    0.0440   -1.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3979   -1.7304    0.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1288   -2.6709    0.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6084   -3.4221   -1.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0940   -2.8850   -2.0401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7158   -0.9072   -1.5864 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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  6 19  1  0
  7 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
 11 24  1  0
M  END
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PDB for HMDB0012175 (5-Acetamidovalerate)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      22.383 -10.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      29.051 -11.155   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      27.717 -10.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.385 -10.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      26.384 -11.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.716 -11.155   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.719 -11.155   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      25.050 -10.385   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0      23.716 -12.695   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      31.719 -12.695   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      33.052 -10.385   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    7                                                       
CONECT    5    3    8                                                       
CONECT    6    1    9    8                                                  
CONECT    7    4   10   11                                                  
CONECT    8    5    6                                                       
CONECT    9    6                                                            
CONECT   10    7                                                            
CONECT   11    7                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
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3D PDB for HMDB0012175 (5-Acetamidovalerate)

COMPND    HMDB0012175
HETATM    1  C1  UNL     1       0.951   3.576   1.468  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.819   2.435   0.828  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.878   2.877   0.401  1.00  0.00           O  
HETATM    4  N1  UNL     1       1.237   1.236   0.883  1.00  0.00           N  
HETATM    5  C3  UNL     1       0.629  -0.021   0.939  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.298  -0.651  -0.358  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.492  -1.928  -0.149  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.955  -2.535  -1.470  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.833  -1.569  -2.162  1.00  0.00           C  
HETATM   10  O2  UNL     1      -1.816  -1.369  -3.387  1.00  0.00           O  
HETATM   11  O3  UNL     1      -2.732  -0.837  -1.411  1.00  0.00           O  
HETATM   12  H1  UNL     1       1.461   4.497   1.471  1.00  0.00           H  
HETATM   13  H2  UNL     1      -0.003   3.571   0.901  1.00  0.00           H  
HETATM   14  H3  UNL     1       0.806   3.175   2.517  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.250   0.655   0.149  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.321   0.125   1.577  1.00  0.00           H  
HETATM   17  H6  UNL     1       1.304  -0.676   1.582  1.00  0.00           H  
HETATM   18  H7  UNL     1       1.328  -0.989  -0.776  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.118   0.044  -1.061  1.00  0.00           H  
HETATM   20  H9  UNL     1      -1.398  -1.730   0.476  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.129  -2.671   0.381  1.00  0.00           H  
HETATM   22  H11 UNL     1      -1.608  -3.422  -1.258  1.00  0.00           H  
HETATM   23  H12 UNL     1      -0.094  -2.885  -2.040  1.00  0.00           H  
HETATM   24  H13 UNL     1      -3.716  -0.907  -1.586  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    3    4
CONECT    4    5   15
CONECT    5    6   16   17
CONECT    6    7   18   19
CONECT    7    8   20   21
CONECT    8    9   22   23
CONECT    9   10   10   11
CONECT   11   24
END
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SMILES for HMDB0012175 (5-Acetamidovalerate)

CC(=O)NCCCCC(O)=O
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INCHI for HMDB0012175 (5-Acetamidovalerate)

InChI=1S/C7H13NO3/c1-6(9)8-5-3-2-4-7(10)11/h2-5H2,1H3,(H,8,9)(H,10,11)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
5-Acetamidovaleric acidGenerator
5-AcetamidopentanoateHMDB
5-Acetamidopentanoic acidHMDB
Chemical FormulaC7H13NO3
Average Molecular Weight159.183
Monoisotopic Molecular Weight159.089543287
IUPAC Name5-acetamidopentanoic acid
Traditional Name5-acetamidopentanoic acid
CAS Registry NumberNot Available
SMILES
CC(=O)NCCCCC(O)=O
InChI Identifier
InChI=1S/C7H13NO3/c1-6(9)8-5-3-2-4-7(10)11/h2-5H2,1H3,(H,8,9)(H,10,11)
InChI KeyTZZSWAXSIGWXOS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentStraight chain fatty acids
Alternative Parents
Substituents
  • Straight chain fatty acid
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028829
KNApSAcK IDNot Available
Chemspider ID388937
KEGG Compound IDC03087
BioCyc ID5-ACETAMIDOVALERATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439903
PDB IDNot Available
ChEBI ID2024
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.