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Showing NP-Card for Leucinic acid (NP0001266)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:59 UTC
NP-MRD IDNP0001266
Secondary Accession NumbersNone
Natural Product Identification
Common NameLeucinic acid
DescriptionLeucinic acid, also known as leucic acid, 2-hydroxyisocaproic acid or 2-hydroxy-4-methylvaleric acid, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. Leucinic acid is a valeric acid derivative having a hydroxy substituent at the 2-position and a methyl substituent at the 4-position. It is an alpha-hydroxy analogue of leucine and a metabolite of the branched-chain amino acid leucine. Leucinic acid is found in all organisms ranging from bacteria to plants to animals. Leucinic acid has been found in a patient with dihydrolipoyl dehydrogenase (DLD) deficiency (PMID: 6688766 ). DLD deficiency is caused by mutations in the DLD gene and is inherited in an autosomal recessive manner. A common feature of dihydrolipoamide dehydrogenase deficiency is a potentially life-threatening buildup of lactic acid in tissues (lactic acidosis), which can cause nausea, vomiting, severe breathing problems, and an abnormal heartbeat. Neurological problems are also common in this condition; the first symptoms in affected infants are often decreased muscle tone (hypotonia) and extreme tiredness (lethargy). As the problems worsen, affected infants can have difficulty feeding, decreased alertness, and seizures. Liver problems can also occur in dihydrolipoamide dehydrogenase deficiency, ranging from an enlarged liver (hepatomegaly) to life-threatening liver failure. In some affected people, liver disease, which can begin anytime from infancy to adulthood, is the primary symptom. Leucinic acid is also present in the urine of patients with short bowel syndrome (PMID: 4018104 )
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001266 (Leucinic acid)


  Mrv1652305271900192D          

  9  8  0  0  0  0            999 V2000
   19.3041  -14.9261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7330  -14.1011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0186  -12.8636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8751  -14.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5896  -13.6886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3041  -14.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1606  -13.6886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8751  -14.9261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0186  -13.6886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  9  1  0  0  0  0
  3  9  2  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  9  1  0  0  0  0
M  END
Download

3D MOL for NP0001266 (Leucinic acid)

HMDB0000665
     RDKit          3D
Leucinic acid
 21 20  0  0  0  0  0  0  0  0999 V2000
   -2.1048    1.1531    0.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0190    0.1372    0.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395   -1.2191    0.0974 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2218    0.5301   -0.2619 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3261   -0.4427   -0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0321   -1.7460   -0.3772 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5713    0.0337   -0.6810 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1874   -0.7181   -1.4565 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0482    1.3106   -0.4513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7297    1.9459   -0.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9724    0.6880   -0.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5116    1.6021    1.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8060    0.1911    1.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3857   -1.3188   -0.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0470   -2.0463    0.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6429   -1.1916    0.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0276    0.6490   -1.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5650    1.5197    0.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5144   -0.4675    1.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3632   -2.4156    0.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9016    1.8052    0.4395 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  1  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
  5 19  1  0
  6 20  1  0
  9 21  1  0
M  END
Download

3D SDF for NP0001266 (Leucinic acid)


  Mrv1652305271900192D          

  9  8  0  0  0  0            999 V2000
   19.3041  -14.9261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7330  -14.1011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0186  -12.8636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8751  -14.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5896  -13.6886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3041  -14.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1606  -13.6886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8751  -14.9261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0186  -13.6886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  9  1  0  0  0  0
  3  9  2  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001266

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O3/c1-4(2)3-5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)

> <INCHI_KEY>
LVRFTAZAXQPQHI-UHFFFAOYSA-N

> <FORMULA>
C6H12O3

> <MOLECULAR_WEIGHT>
132.1577

> <EXACT_MASS>
132.07864425

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
13.649767203036058

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-4-methylpentanoic acid

> <ALOGPS_LOGP>
0.50

> <JCHEM_LOGP>
0.7822806383333333

> <ALOGPS_LOGS>
-0.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.276112311717824

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.257807082104199

> <JCHEM_PKA_STRONGEST_BASIC>
-3.801045430820605

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
32.513400000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
leucate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001266 (Leucinic acid)

HMDB0000665
     RDKit          3D
Leucinic acid
 21 20  0  0  0  0  0  0  0  0999 V2000
   -2.1048    1.1531    0.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0190    0.1372    0.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395   -1.2191    0.0974 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2218    0.5301   -0.2619 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3261   -0.4427   -0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0321   -1.7460   -0.3772 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5713    0.0337   -0.6810 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1874   -0.7181   -1.4565 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0482    1.3106   -0.4513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7297    1.9459   -0.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9724    0.6880   -0.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5116    1.6021    1.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8060    0.1911    1.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3857   -1.3188   -0.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0470   -2.0463    0.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6429   -1.1916    0.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0276    0.6490   -1.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5650    1.5197    0.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5144   -0.4675    1.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3632   -2.4156    0.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9016    1.8052    0.4395 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  1  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
  5 19  1  0
  6 20  1  0
  9 21  1  0
M  END
Download

PDB for NP0001266 (Leucinic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      36.034 -27.862   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      38.702 -26.322   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      37.368 -24.012   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      33.367 -26.322   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      34.701 -25.552   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      36.034 -26.322   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      32.033 -25.552   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      33.367 -27.862   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      37.368 -25.552   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    9                                                            
CONECT    3    9                                                            
CONECT    4    5    7    8                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5    9                                                  
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    2    3    6                                                  
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for NP0001266 (Leucinic acid)

COMPND    HMDB0000665
HETATM    1  C1  UNL     1      -2.105   1.153   0.206  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.019   0.137   0.501  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.539  -1.219   0.097  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.222   0.530  -0.262  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.326  -0.443  -0.005  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.032  -1.746  -0.377  1.00  0.00           O  
HETATM    7  C6  UNL     1       2.571   0.034  -0.681  1.00  0.00           C  
HETATM    8  O2  UNL     1       3.187  -0.718  -1.456  1.00  0.00           O  
HETATM    9  O3  UNL     1       3.048   1.311  -0.451  1.00  0.00           O  
HETATM   10  H1  UNL     1      -1.730   1.946  -0.459  1.00  0.00           H  
HETATM   11  H2  UNL     1      -2.972   0.688  -0.330  1.00  0.00           H  
HETATM   12  H3  UNL     1      -2.512   1.602   1.137  1.00  0.00           H  
HETATM   13  H4  UNL     1      -0.806   0.191   1.584  1.00  0.00           H  
HETATM   14  H5  UNL     1      -1.386  -1.319  -0.999  1.00  0.00           H  
HETATM   15  H6  UNL     1      -1.047  -2.046   0.637  1.00  0.00           H  
HETATM   16  H7  UNL     1      -2.643  -1.192   0.285  1.00  0.00           H  
HETATM   17  H8  UNL     1       0.028   0.649  -1.343  1.00  0.00           H  
HETATM   18  H9  UNL     1       0.565   1.520   0.105  1.00  0.00           H  
HETATM   19  H10 UNL     1       1.514  -0.468   1.102  1.00  0.00           H  
HETATM   20  H11 UNL     1       1.363  -2.416   0.269  1.00  0.00           H  
HETATM   21  H12 UNL     1       2.902   1.805   0.439  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    7   19
CONECT    6   20
CONECT    7    8    8    9
CONECT    9   21
END
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SMILES for NP0001266 (Leucinic acid)

CC(C)CC(O)C(O)=O
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INCHI for NP0001266 (Leucinic acid)

InChI=1S/C6H12O3/c1-4(2)3-5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)
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View in JSmol
Synonyms
ValueSource
2-Hydroxyisocaproic acidChEBI
2-Hydroxyisohexanoic acidChEBI
alpha-Hydroxyisocaproic acidChEBI
Leucic acidChEBI
2-HydroxyisocaproateGenerator
2-HydroxyisohexanoateGenerator
a-HydroxyisocaproateGenerator
a-Hydroxyisocaproic acidGenerator
alpha-HydroxyisocaproateGenerator
Α-hydroxyisocaproateGenerator
Α-hydroxyisocaproic acidGenerator
LeucateGenerator
LeucinateGenerator
alpha-Hydroxyisocaproic acid, (R)-isomerHMDB
alpha-Hydroxyisocaproic acid, calcium (2:1) salt, (S)-isomerHMDB
alpha-Hydroxyisocaproic acid, monosodium saltHMDB
alpha-Hydroxyisocaproic acid, (S)-isomerHMDB
2-Hydroxy-4-methyl-valerateHMDB
2-Hydroxy-4-methyl-valeric acidHMDB
2-Hydroxy-4-methylpentanoateHMDB
2-Hydroxy-4-methylpentanoic acidHMDB
2-Hydroxy-4-methylvalerateHMDB
2-Hydroxy-4-methylvaleric acidHMDB
a-Hydroxy-iso-caproateHMDB
a-Hydroxy-iso-caproic acidHMDB
alpha-Hydroxy-iso-caproateHMDB
alpha-Hydroxy-iso-caproic acidHMDB
DL-2-Hydroxy-4-methylpentanoateHMDB
DL-2-Hydroxy-4-methylpentanoic acidHMDB
DL-2-HydroxyisocaproateHMDB
DL-2-Hydroxyisocaproic acidHMDB
DL-a-HydroxyisocaproateHMDB
DL-a-Hydroxyisocaproic acidHMDB
DL-alpha-HydroxyisocaproateHMDB
DL-alpha-Hydroxyisocaproic acidHMDB
DL-LeucateHMDB
DL-Leucic acidHMDB
Leucinic acidChEBI
D-LeucateGenerator
Chemical FormulaC6H12O3
Average Mass132.1577 Da
Monoisotopic Mass132.07864 Da
IUPAC Name2-hydroxy-4-methylpentanoic acid
Traditional Nameleucate
CAS Registry Number498-36-2
SMILES
CC(C)CC(O)C(O)=O
InChI Identifier
InChI=1S/C6H12O3/c1-4(2)3-5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)
InChI KeyLVRFTAZAXQPQHI-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
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
Anas platyrhynchosFooDB
AnatidaeFooDB
Annona muricataLOTUS Database
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Branched fatty acid
  • Hydroxy fatty acid
  • Methyl-branched fatty acid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point76.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point249.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility886 mg/mLNot Available
LogP0.522 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility124 g/LALOGPS
logP0.5ALOGPS
logP0.78ChemAxon
logS-0.03ALOGPS
pKa (Strongest Acidic)4.26ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity32.51 m³·mol⁻¹ChemAxon
Polarizability13.65 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000665
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022171
KNApSAcK IDNot Available
Chemspider ID83753
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5635
PubChem Compound92779
PDB IDNot Available
ChEBI ID59783
Good Scents IDrw1488981
References
General References
  1. Kuhara T, Shinka T, Inoue Y, Matsumoto M, Yoshino M, Sakaguchi Y, Matsumoto I: Studies of urinary organic acid profiles of a patient with dihydrolipoyl dehydrogenase deficiency. Clin Chim Acta. 1983 Sep 30;133(2):133-40. [PubMed:6688766 ]
  2. Jakobs C, Sweetman L, Nyhan WL: Hydroxy acid metabolites of branched-chain amino acids in amniotic fluid. Clin Chim Acta. 1984 Jul 16;140(2):157-66. [PubMed:6467607 ]
  3. Spaapen LJ, Ketting D, Wadman SK, Bruinvis L, Duran M: Urinary D-4-hydroxyphenyllactate, D-phenyllactate and D-2-hydroxyisocaproate, abnormalities of bacterial origin. J Inherit Metab Dis. 1987;10(4):383-90. [PubMed:3126358 ]
  4. Haan E, Brown G, Bankier A, Mitchell D, Hunt S, Blakey J, Barnes G: Severe illness caused by the products of bacterial metabolism in a child with a short gut. Eur J Pediatr. 1985 May;144(1):63-5. [PubMed:4018104 ]
  5. Castrillo JI, Zeef LA, Hoyle DC, Zhang N, Hayes A, Gardner DC, Cornell MJ, Petty J, Hakes L, Wardleworth L, Rash B, Brown M, Dunn WB, Broadhurst D, O'Donoghue K, Hester SS, Dunkley TP, Hart SR, Swainston N, Li P, Gaskell SJ, Paton NW, Lilley KS, Kell DB, Oliver SG: Growth control of the eukaryote cell: a systems biology study in yeast. J Biol. 2007;6(2):4. doi: 10.1186/jbiol54. [PubMed:17439666 ]