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Showing NP-Card for Ketoleucine (NP0001215)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-05-31 19:05:02 UTC
NP-MRD IDNP0001215
Secondary Accession NumbersNone
Natural Product Identification
Common NameKetoleucine
DescriptionKetoleucine is an abnormal metabolite that arises from the incomplete breakdown of branched-chain amino acids. Ketoleucine is both a neurotoxin and a metabotoxin. A neurotoxin causes damage to nerve cells and nerve tissues. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of ketoleucine are associated with maple syrup urine disease (MSUD). MSUD is a metabolic disorder caused by a deficiency of the branched-chain alpha-keto acid dehydrogenase complex (BCKDC), leading to a buildup of the branched-chain amino acids (leucine, isoleucine, and valine) and their toxic by-products (ketoacids) in the blood and urine. The symptoms of MSUD often show in infancy and lead to severe brain damage if untreated. MSUD may also present later depending on the severity of the disease. If left untreated in older individuals, during times of metabolic crisis, symptoms of the condition include uncharacteristically inappropriate, extreme, or erratic behaviour and moods, hallucinations, anorexia, weight loss, anemia, diarrhea, vomiting, dehydration, lethargy, oscillating hypertonia and hypotonia, ataxia, seizures, hypoglycemia, ketoacidosis, opisthotonus, pancreatitis, rapid neurological decline, and coma. In maple syrup urine disease, the brain concentration of branched-chain ketoacids can increase 10- to 20-fold. This leads to a depletion of glutamate and a consequent reduction in the concentration of brain glutamine, aspartate, alanine, and other amino acids. The result is a compromise of energy metabolism because of a failure of the malate-aspartate shuttle and a diminished rate of protein synthesis (PMID: 15930465 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001215 (Ketoleucine)


  Mrv1652309042000062D          

  9  8  0  0  0  0            999 V2000
10023.952810024.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10024.669810024.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10025.383310024.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10026.098710024.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10025.383310023.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10023.238410024.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10022.523910024.1004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10023.238410025.3371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10023.952810023.2754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1  9  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
Download

3D MOL for NP0001215 (Ketoleucine)

HMDB0000695
     RDKit          3D
Ketoleucine
 19 18  0  0  0  0  0  0  0  0999 V2000
   -2.0703    0.1757   -1.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9527   -0.5142   -0.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4345   -0.7518    1.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2662    0.3326   -0.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4513   -0.1546    0.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5124   -1.2279    0.8564 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6774    0.6181    0.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6581    1.7008   -0.5434 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8562    0.2187    0.7443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0560    0.0073   -0.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8598    1.2579   -1.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1308   -0.2351   -2.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8046   -1.4936   -0.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5389   -0.9069    0.9590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2770    0.1382    1.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0344   -1.6846    1.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0672    1.3723   -0.1625 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5057    0.4166   -1.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1646    0.7304    1.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  9 19  1  0
M  END
Download

3D SDF for NP0001215 (Ketoleucine)


  Mrv1652309042000062D          

  9  8  0  0  0  0            999 V2000
10023.952810024.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10024.669810024.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10025.383310024.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10026.098710024.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10025.383310023.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10023.238410024.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10022.523910024.1004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10023.238410025.3371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10023.952810023.2754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1  9  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0001215

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O3/c1-4(2)3-5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)

> <INCHI_KEY>
BKAJNAXTPSGJCU-UHFFFAOYSA-N

> <FORMULA>
C6H10O3

> <MOLECULAR_WEIGHT>
130.1418

> <EXACT_MASS>
130.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
12.995994785498697

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-methyl-2-oxopentanoic acid

> <ALOGPS_LOGP>
0.82

> <JCHEM_LOGP>
1.4979975616666668

> <ALOGPS_LOGS>
-1.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.528051095084082

> <JCHEM_PKA_STRONGEST_BASIC>
-9.662090237480372

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
31.7662

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.76e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ketoisocaproate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001215 (Ketoleucine)

HMDB0000695
     RDKit          3D
Ketoleucine
 19 18  0  0  0  0  0  0  0  0999 V2000
   -2.0703    0.1757   -1.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9527   -0.5142   -0.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4345   -0.7518    1.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2662    0.3326   -0.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4513   -0.1546    0.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5124   -1.2279    0.8564 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6774    0.6181    0.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6581    1.7008   -0.5434 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8562    0.2187    0.7443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0560    0.0073   -0.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8598    1.2579   -1.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1308   -0.2351   -2.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8046   -1.4936   -0.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5389   -0.9069    0.9590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2770    0.1382    1.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0344   -1.6846    1.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0672    1.3723   -0.1625 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5057    0.4166   -1.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1646    0.7304    1.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  9 19  1  0
M  END
Download

PDB for NP0001215 (Ketoleucine)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0    8711.3798711.654   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8712.7178712.423   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8714.0498711.654   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8715.3848712.423   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8714.0498710.114   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8710.0458712.423   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8708.7118711.654   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8710.0458713.963   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8711.3798710.114   0.000  0.00  0.00           O+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    1    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    1                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for NP0001215 (Ketoleucine)

COMPND    HMDB0000695
HETATM    1  C1  UNL     1      -2.070   0.176  -1.161  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.953  -0.514  -0.379  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.435  -0.752   1.007  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.266   0.333  -0.494  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.451  -0.155   0.187  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.512  -1.228   0.856  1.00  0.00           O  
HETATM    7  C6  UNL     1       2.677   0.618   0.118  1.00  0.00           C  
HETATM    8  O2  UNL     1       2.658   1.701  -0.543  1.00  0.00           O  
HETATM    9  O3  UNL     1       3.856   0.219   0.744  1.00  0.00           O  
HETATM   10  H1  UNL     1      -3.056   0.007  -0.694  1.00  0.00           H  
HETATM   11  H2  UNL     1      -1.860   1.258  -1.235  1.00  0.00           H  
HETATM   12  H3  UNL     1      -2.131  -0.235  -2.191  1.00  0.00           H  
HETATM   13  H4  UNL     1      -0.805  -1.494  -0.871  1.00  0.00           H  
HETATM   14  H5  UNL     1      -2.539  -0.907   0.959  1.00  0.00           H  
HETATM   15  H6  UNL     1      -1.277   0.138   1.656  1.00  0.00           H  
HETATM   16  H7  UNL     1      -1.034  -1.685   1.469  1.00  0.00           H  
HETATM   17  H8  UNL     1       0.067   1.372  -0.163  1.00  0.00           H  
HETATM   18  H9  UNL     1       0.506   0.417  -1.588  1.00  0.00           H  
HETATM   19  H10 UNL     1       4.165   0.730   1.560  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    4   13
CONECT    3   14   15   16
CONECT    4    5   17   18
CONECT    5    6    6    7
CONECT    7    8    8    9
CONECT    9   19
END
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SMILES for NP0001215 (Ketoleucine)

CC(C)CC(=O)C(O)=O
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INCHI for NP0001215 (Ketoleucine)

InChI=1S/C6H10O3/c1-4(2)3-5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)
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View in JSmol
Synonyms
ValueSource
2-oxo-4-METHYLPENTANOIC ACIDChEBI
2-OxoisocaproateChEBI
4-Methyl-2-oxopentanoateChEBI
4-Methyl-2-oxovaleric acidChEBI
alpha-Ketoisocaproic acidChEBI
2-oxo-4-METHYLPENTANOateGenerator
2-Oxoisocaproic acidGenerator
4-Methyl-2-oxopentanoic acidGenerator
4-Methyl-2-oxovalerateGenerator
a-KetoisocaproateGenerator
a-Ketoisocaproic acidGenerator
alpha-KetoisocaproateGenerator
Α-ketoisocaproateGenerator
Α-ketoisocaproic acidGenerator
2-Keto-4-methylvalerateHMDB
2-Keto-4-methylvaleric acidHMDB
2-KetoisocaproateHMDB
2-Ketoisocaproic acidHMDB
2-oxo-4-MethylvalerateHMDB
2-oxo-4-Methylvaleric acidHMDB
2-OxoleucineHMDB
4-Methyl-2-oxo-valerateHMDB
4-Methyl-2-oxo-valeric acidHMDB
a-KetoisocapronateHMDB
a-Ketoisocapronic acidHMDB
a-OxoisocaproateHMDB
a-Oxoisocaproic acidHMDB
alpha-Keto-isocaproateHMDB
alpha-Keto-isocaproic acidHMDB
alpha-KetoisocapronateHMDB
alpha-Ketoisocapronic acidHMDB
alpha-OxoisocaproateHMDB
alpha-Oxoisocaproic acidHMDB
KetoisocaproateHMDB
Ketoisocaproic acidHMDB
MethyloxovalerateHMDB
Methyloxovaleric acidHMDB
OxoisocaproateHMDB
Oxoisocaproic acidHMDB
Keto-leucineHMDB
Chemical FormulaC6H10O3
Average Mass130.1418 Da
Monoisotopic Mass130.06299 Da
IUPAC Name4-methyl-2-oxopentanoic acid
Traditional Nameketoisocaproate
CAS Registry Number816-66-0
SMILES
CC(C)CC(=O)C(O)=O
InChI Identifier
InChI=1S/C6H10O3/c1-4(2)3-5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)
InChI KeyBKAJNAXTPSGJCU-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-05-31View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloysia triphyllaFooDB
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anser anserFooDB
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arachis hypogaeaFooDB
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Basella albaFooDB
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
Borago officinalisFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Bubalus bubalisFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Canarium ovatumFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papaya L.FooDB
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chlamydomonas reinhardtiiLOTUS Database
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
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ColumbaFooDB
ColumbidaeFooDB
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Cucumis sativus L.FooDB
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Cymbopogon citratusFooDB
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Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
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ElaeisFooDB
Eleocharis dulcisFooDB
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Helianthus annuus L.FooDB
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Hibiscus sabbariffaFooDB
Hippophae rhamnoidesFooDB
Homo sapiensLOTUS Database
Hordeum vulgareFooDB
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Illicium verumFooDB
Ipomoea aquaticaFooDB
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LeporidaeFooDB
Lepus timidusFooDB
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Linum usitatissimumFooDB
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LupinusFooDB
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MacadamiaFooDB
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Medicago sativaFooDB
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Mentha arvensisFooDB
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Mentha x piperitaFooDB
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MorchellaceaeFooDB
Morella rubraFooDB
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MorusFooDB
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MyricaFooDB
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OpuntiaFooDB
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Opuntia macrorhizaFooDB
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Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
Panax ginsengFooDB
Pangium eduleFooDB
Panicum miliaceumFooDB
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PhysalisFooDB
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Pimpinella anisumFooDB
PinusFooDB
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Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
Pleurotus ostreatusFooDB
Polygonum alpinumFooDB
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
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Prunus tomentosaFooDB
Prunus virginianaFooDB
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Raphanus sativusFooDB
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Rheum rhabarbarumFooDB
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
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Rubus idaeusFooDB
Rubus occidentalisFooDB
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RumexFooDB
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Salix pulchraFooDB
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Satureja hortensis L.FooDB
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Scorzonera hispanicaFooDB
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Sechium eduleFooDB
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    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
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Trigonella foenum-graecumFooDB
TriticumFooDB
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Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
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Vaccinium ovalifoliumFooDB
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Vigna aconitifoliaFooDB
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Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
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Vitis labruscaFooDB
Vitis rotundifoliaFooDB
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Vitis vinifera L.FooDB
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ZizaniaFooDB
Zizania aquaticaFooDB
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Species Where Detected
Species NameSourceReference
Escherichia coliKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-chain keto acids and derivatives
Alternative Parents
Substituents
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Short-chain keto acid
  • Alpha-keto acid
  • Fatty acyl
  • Alpha-hydroxy ketone
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point8 - 10 °CNot Available
Boiling Point251.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility32 mg/mLNot Available
LogP0.133 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility6.76 g/LALOGPS
logP0.82ALOGPS
logP1.5ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)3.53ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity31.77 m³·mol⁻¹ChemAxon
Polarizability13 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000695
DrugBank IDDB03229
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030510
KNApSAcK IDC00019677
Chemspider ID69
KEGG Compound IDC00233
BioCyc ID2K-4CH3-PENTANOATE
BiGG ID34334
Wikipedia LinkNot Available
METLIN ID5663
PubChem Compound70
PDB IDNot Available
ChEBI ID48430
Good Scents IDrw1047101
References
General References
  1. Martin PM, Gopal E, Ananth S, Zhuang L, Itagaki S, Prasad BM, Smith SB, Prasad PD, Ganapathy V: Identity of SMCT1 (SLC5A8) as a neuron-specific Na+-coupled transporter for active uptake of L-lactate and ketone bodies in the brain. J Neurochem. 2006 Jul;98(1):279-88. [PubMed:16805814 ]
  2. Yudkoff M, Daikhin Y, Nissim I, Horyn O, Luhovyy B, Lazarow A, Nissim I: Brain amino acid requirements and toxicity: the example of leucine. J Nutr. 2005 Jun;135(6 Suppl):1531S-8S. [PubMed:15930465 ]
  3. Chow LS, Albright RC, Bigelow ML, Toffolo G, Cobelli C, Nair KS: Mechanism of insulin's anabolic effect on muscle: measurements of muscle protein synthesis and breakdown using aminoacyl-tRNA and other surrogate measures. Am J Physiol Endocrinol Metab. 2006 Oct;291(4):E729-36. Epub 2006 May 16. [PubMed:16705065 ]
  4. Wang Y, Holmes E, Nicholson JK, Cloarec O, Chollet J, Tanner M, Singer BH, Utzinger J: Metabonomic investigations in mice infected with Schistosoma mansoni: an approach for biomarker identification. Proc Natl Acad Sci U S A. 2004 Aug 24;101(34):12676-81. Epub 2004 Aug 16. [PubMed:15314235 ]
  5. Mitch WE, Walser M, Sapir DG: Nitrogen sparing induced by leucine compared with that induced by its keto analogue, alpha-ketoisocaproate, in fasting obese man. J Clin Invest. 1981 Feb;67(2):553-62. [PubMed:7462428 ]
  6. Sgaravatti AM, Rosa RB, Schuck PF, Ribeiro CA, Wannmacher CM, Wyse AT, Dutra-Filho CS, Wajner M: Inhibition of brain energy metabolism by the alpha-keto acids accumulating in maple syrup urine disease. Biochim Biophys Acta. 2003 Nov 20;1639(3):232-8. [PubMed:14636955 ]
  7. Schadewaldt P, Hammen HW, Ott AC, Wendel U: Renal clearance of branched-chain L-amino and 2-oxo acids in maple syrup urine disease. J Inherit Metab Dis. 1999 Aug;22(6):706-22. [PubMed:10472531 ]
  8. Hachey DL, Patterson BW, Reeds PJ, Elsas LJ: Isotopic determination of organic keto acid pentafluorobenzyl esters in biological fluids by negative chemical ionization gas chromatography/mass spectrometry. Anal Chem. 1991 May 1;63(9):919-23. [PubMed:1858984 ]
  9. Farias HR, Gabriel JR, Cecconi ML, Lemos IS, de Rezende VL, Wessler LB, Duarte MB, Scaini G, de Oliveira J, Streck EL: The metabolic effect of alpha-ketoisocaproic acid: in vivo and in vitro studies. Metab Brain Dis. 2021 Jan;36(1):185-192. doi: 10.1007/s11011-020-00626-y. Epub 2020 Oct 9. [PubMed:33034842 ]