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Showing NP-Card for Beta-Leucine (NP0001195)

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Record Information
Version1.0
Created at2006-08-13 02:23:00 UTC
Updated at2020-11-24 22:21:32 UTC
NP-MRD IDNP0001195
Secondary Accession NumbersNone
Natural Product Identification
Common NameBeta-Leucine
DescriptionBeta-leucine is a metabolite that is in the middle of a controversy over its presence in the human body. While there are reports that claim it as a human metabolite, there are others that deny its existence. Two examples:. Circulating levels of beta-leucine are elevated in the cobalamin-deficient state of pernicious anemia. Levels of leucine, on the other hand, are much lower. It is proposed that leucine 2,3-aminomutase, the cobalamin-dependent enzyme that catalyzes the interconversion of leucine and beta-leucine, is the affected enzyme in pernicious anemia and causes these results by preventing the synthesis of leucine from beta-leucine. The synthesis of leucine by human leukocytes and hair roots and by rat liver extracts has been shown to occur when either branched chain fatty acids or valine metabolites are the substances. The synthesis is dependent upon adenosylcobalamin and is inhibited by intrinsic factor (PMID: 7430116 ). Using forms of beta-leucine and leucine that contain several deuterium atoms in place of several hydrogen atoms as internal standards, techniques have been developed which make it possible to detect and quantitate as little as 0.1 Mumol/liter of beta-leucine or leucine in human serum and in incubations containing rat liver supernatant. Beta-Leucine was not detectable, i.E. Less than 0.1 Mumol/liter, in any sera from 50 normal human subjects or in any sera from 50 cobalamin-deficient patients. Experiments in which beta-leucine, leucine, isostearic acid, or isocaproic acid were incubated with rat liver supernatant in the presence or absence of adenosylcobalamin or cobalamin-binding protein failed to demonstrate the formation of leucine or beta-leucine or their interconversion under any of the conditions studied. We conclude that beta-leucine is not present in human blood and that the existence of leucine 2,3-aminomutase in mammalian tissues remains to be established (PMID 3356699 ). Beta-leucine is found to be associated with cobalamin deficiency, which is an inborn error of metabolism.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001195 (Beta-Leucine)


  Mrv1652305271900042D          

  9  8  0  0  1  0            999 V2000
   19.2888  -15.3554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5744  -16.5929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1455  -16.5929    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1455  -15.7679    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.4309  -15.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8599  -15.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7164  -15.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4309  -14.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5744  -15.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2  9  2  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  9  1  0  0  0  0
M  END
Download

3D MOL for NP0001195 (Beta-Leucine)

HMDB0003640
     RDKit          3D
Beta-Leucine
 22 21  0  0  0  0  0  0  0  0999 V2000
   -1.9699   -0.6975    0.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0591    0.4086    0.5086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2701    1.6383   -0.3564 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3984    0.0211    0.5852 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5225   -1.0663    1.5154 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0361   -0.3267   -0.7078 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4565   -0.6671   -0.4002 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9120   -1.8247   -0.5148 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3463    0.3232    0.0427 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5651   -0.3476   -0.8222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4661   -1.6330   -0.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7549   -0.9349    0.8394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3595    0.6966    1.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3120    2.1073   -0.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8402    1.3803   -1.2711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8643    2.4256    0.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9219    0.9243    0.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3627   -1.9528    0.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1471   -0.9240    2.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5934   -1.2235   -1.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0612    0.4610   -1.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9974    1.2117    0.3982 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
  4  6  1  0
  6  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  1
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  9 22  1  0
M  END
Download

3D SDF for NP0001195 (Beta-Leucine)


  Mrv1652305271900042D          

  9  8  0  0  1  0            999 V2000
   19.2888  -15.3554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5744  -16.5929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1455  -16.5929    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1455  -15.7679    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.4309  -15.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8599  -15.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7164  -15.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4309  -14.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5744  -15.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2  9  2  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001195

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H](N)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H13NO2/c1-4(2)5(7)3-6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t5-/m0/s1

> <INCHI_KEY>
GLUJNGJDHCTUJY-YFKPBYRVSA-N

> <FORMULA>
C6H13NO2

> <MOLECULAR_WEIGHT>
131.1729

> <EXACT_MASS>
131.094628665

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
14.06563619628169

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-3-amino-4-methylpentanoic acid

> <ALOGPS_LOGP>
-2.14

> <JCHEM_LOGP>
-1.8698627027982233

> <ALOGPS_LOGS>
-0.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.389495820581845

> <JCHEM_PKA_STRONGEST_BASIC>
10.599975271720838

> <JCHEM_POLAR_SURFACE_AREA>
63.31999999999999

> <JCHEM_REFRACTIVITY>
34.117200000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.26e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-leucine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001195 (Beta-Leucine)

HMDB0003640
     RDKit          3D
Beta-Leucine
 22 21  0  0  0  0  0  0  0  0999 V2000
   -1.9699   -0.6975    0.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0591    0.4086    0.5086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2701    1.6383   -0.3564 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3984    0.0211    0.5852 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5225   -1.0663    1.5154 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0361   -0.3267   -0.7078 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4565   -0.6671   -0.4002 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9120   -1.8247   -0.5148 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3463    0.3232    0.0427 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5651   -0.3476   -0.8222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4661   -1.6330   -0.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7549   -0.9349    0.8394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3595    0.6966    1.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3120    2.1073   -0.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8402    1.3803   -1.2711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8643    2.4256    0.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9219    0.9243    0.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3627   -1.9528    0.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1471   -0.9240    2.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5934   -1.2235   -1.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0612    0.4610   -1.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9974    1.2117    0.3982 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
  4  6  1  0
  6  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  1
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  9 22  1  0
M  END
Download

PDB for NP0001195 (Beta-Leucine)

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      36.006 -28.663   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      34.672 -30.973   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      32.005 -30.973   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      32.005 -29.433   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.671 -28.663   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      33.338 -28.663   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      29.337 -29.433   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      30.671 -27.123   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      34.672 -29.433   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3    4                                                            
CONECT    4    3    5    6                                                  
CONECT    5    4    7    8                                                  
CONECT    6    4    9                                                       
CONECT    7    5                                                            
CONECT    8    5                                                            
CONECT    9    1    2    6                                                  
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for NP0001195 (Beta-Leucine)

COMPND    HMDB0003640
HETATM    1  C1  UNL     1      -1.970  -0.698   0.068  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.059   0.409   0.509  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.270   1.638  -0.356  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.398   0.021   0.585  1.00  0.00           C  
HETATM    5  N1  UNL     1       0.522  -1.066   1.515  1.00  0.00           N  
HETATM    6  C5  UNL     1       1.036  -0.327  -0.708  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.457  -0.667  -0.400  1.00  0.00           C  
HETATM    8  O1  UNL     1       2.912  -1.825  -0.515  1.00  0.00           O  
HETATM    9  O2  UNL     1       3.346   0.323   0.043  1.00  0.00           O  
HETATM   10  H1  UNL     1      -2.565  -0.348  -0.822  1.00  0.00           H  
HETATM   11  H2  UNL     1      -1.466  -1.633  -0.177  1.00  0.00           H  
HETATM   12  H3  UNL     1      -2.755  -0.935   0.839  1.00  0.00           H  
HETATM   13  H4  UNL     1      -1.360   0.697   1.535  1.00  0.00           H  
HETATM   14  H5  UNL     1      -0.312   2.107  -0.653  1.00  0.00           H  
HETATM   15  H6  UNL     1      -1.840   1.380  -1.271  1.00  0.00           H  
HETATM   16  H7  UNL     1      -1.864   2.426   0.171  1.00  0.00           H  
HETATM   17  H8  UNL     1       0.922   0.924   0.988  1.00  0.00           H  
HETATM   18  H9  UNL     1       0.363  -1.953   0.995  1.00  0.00           H  
HETATM   19  H10 UNL     1      -0.147  -0.924   2.305  1.00  0.00           H  
HETATM   20  H11 UNL     1       0.593  -1.224  -1.192  1.00  0.00           H  
HETATM   21  H12 UNL     1       1.061   0.461  -1.464  1.00  0.00           H  
HETATM   22  H13 UNL     1       2.997   1.212   0.398  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    4   13
CONECT    3   14   15   16
CONECT    4    5    6   17
CONECT    5   18   19
CONECT    6    7   20   21
CONECT    7    8    8    9
CONECT    9   22
END
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SMILES for NP0001195 (Beta-Leucine)

CC(C)[C@@H](N)CC(O)=O
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INCHI for NP0001195 (Beta-Leucine)

InChI=1S/C6H13NO2/c1-4(2)5(7)3-6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t5-/m0/s1
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View in JSmol
Synonyms
ValueSource
(S)-Homo-beta-valChEBI
(S)-Homo-b-valGenerator
(S)-Homo-β-valGenerator
b-LeucineGenerator
Β-leucineGenerator
3-Amino-4-methylpentanoic acidHMDB
beta-2-Amino-4-methylvaleric acidHMDB
L-beta-LeucineHMDB
(3S)-b-LeucineHMDB
(3S)-Β-leucineHMDB
beta-LeucineMeSH
Chemical FormulaC6H13NO2
Average Mass131.1729 Da
Monoisotopic Mass131.09463 Da
IUPAC Name(3S)-3-amino-4-methylpentanoic acid
Traditional Nameβ-leucine
CAS Registry Number5699-54-7
SMILES
CC(C)[C@@H](N)CC(O)=O
InChI Identifier
InChI=1S/C6H13NO2/c1-4(2)5(7)3-6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t5-/m0/s1
InChI KeyGLUJNGJDHCTUJY-YFKPBYRVSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 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
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 beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentBeta amino acids and derivatives
Alternative Parents
Substituents
  • Beta amino acid or derivatives
  • Amino fatty acid
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Fatty acyl
  • Fatty acid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Amine
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.778Not Available
Predicted Properties
PropertyValueSource
Water Solubility126 g/LALOGPS
logP-2.1ALOGPS
logP-1.9ChemAxon
logS-0.02ALOGPS
pKa (Strongest Acidic)4.39ChemAxon
pKa (Strongest Basic)10.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity34.12 m³·mol⁻¹ChemAxon
Polarizability14.07 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003640
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023208
KNApSAcK IDNot Available
Chemspider ID388796
KEGG Compound IDC02486
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkΒ-Leucine
METLIN IDNot Available
PubChem Compound439734
PDB IDNot Available
ChEBI ID86261
Good Scents IDNot Available
References
General References
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