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Showing NP-Card for N-Acetylleucine (NP0091584)

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Record Information
Version2.0
Created at2022-05-11 18:41:55 UTC
Updated at2022-05-11 18:41:55 UTC
NP-MRD IDNP0091584
Secondary Accession NumbersNone
Natural Product Identification
Common NameN-Acetylleucine
DescriptionN-Acetylleucine, also known as N-acetyl-leu or tanganil, belongs to the class of organic compounds known as leucine and derivatives. Leucine and derivatives are compounds containing leucine or a derivative thereof resulting from reaction of leucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. The N-acetyl derivative of L-leucine. N-Acetylleucine is found in Apis cerana and Mus musculus. N-Acetylleucine was first documented in 1986 (PMID: 3473611). N-Acetylleucine is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 21185819) (PMID: 22227165).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0091584 (N-Acetylleucine)


  Mrv0541 02241201532D          

 12 11  0  0  1  0            999 V2000
   14.2606   -9.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4357   -9.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0232  -10.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0232   -8.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1983   -8.6956    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.7858   -9.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1983  -10.1246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9609   -9.4101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7858   -7.9811    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1983   -7.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7858   -6.5527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0232   -7.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  1  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
Download

3D MOL for NP0091584 (N-Acetylleucine)

     RDKit          3D

 27 26  0  0  0  0  0  0  0  0999 V2000
    3.2156   -1.8151    0.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5047   -0.6803   -0.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1213   -0.1303   -1.1060 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2657   -0.1438    0.3197 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5922    0.9661   -0.3625 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6532    0.3123   -0.9747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5536   -0.3729   -0.0636 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6854   -1.0059   -0.9397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3466    0.4210    0.9366 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4114    2.1671    0.3666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6313    2.5621    0.9589 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5451    3.0607    0.4858 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3050   -1.6534    1.5902 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6110   -2.7289    0.3065 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2299   -1.9619    0.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7788   -0.4817    1.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2553    1.2158   -1.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3047   -0.3496   -1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2087    1.1552   -1.4785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0961   -1.2583    0.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4349   -0.2277   -1.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2558   -1.3803   -1.8823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2092   -1.7995   -0.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8585    1.2539    0.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8428    0.5776    1.9280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1920   -0.3085    1.2351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4365    2.6065    0.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  9  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5 10  1  0
 10 12  1  0
 10 11  2  0
  8 21  1  0
  8 22  1  0
  8 23  1  0
  7 20  1  1
  9 24  1  0
  9 25  1  0
  9 26  1  0
  6 18  1  0
  6 19  1  0
  5 17  1  6
  4 16  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
 12 27  1  0
M  END
Download

3D SDF for NP0091584 (N-Acetylleucine)


  Mrv0541 02241201532D          

 12 11  0  0  1  0            999 V2000
   14.2606   -9.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4357   -9.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0232  -10.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0232   -8.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1983   -8.6956    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.7858   -9.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1983  -10.1246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9609   -9.4101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7858   -7.9811    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1983   -7.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7858   -6.5527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0232   -7.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  1  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0091584

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H15NO3/c1-5(2)4-7(8(11)12)9-6(3)10/h5,7H,4H2,1-3H3,(H,9,10)(H,11,12)/t7-/m0/s1

> <INCHI_KEY>
WXNXCEHXYPACJF-ZETCQYMHSA-N

> <FORMULA>
C8H15NO3

> <MOLECULAR_WEIGHT>
173.2096

> <EXACT_MASS>
173.105193351

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
18.08855602833691

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-acetamido-4-methylpentanoic acid

> <ALOGPS_LOGP>
0.78

> <JCHEM_LOGP>
0.4942454446666666

> <ALOGPS_LOGS>
-1.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.926251046208662

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.201763442181692

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1652895359108353

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
43.614700000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.09e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-acetyl-leu

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0091584 (N-Acetylleucine)

Download
PDB for NP0091584 (N-Acetylleucine)
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      26.620 -17.566   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      25.080 -17.566   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.310 -18.899   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.310 -16.232   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.770 -16.232   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.000 -17.566   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      22.770 -18.899   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      20.460 -17.566   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      22.000 -14.898   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      22.770 -13.565   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      22.000 -12.232   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      24.310 -13.565   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

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3D PDB for NP0091584 (N-Acetylleucine)
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SMILES for NP0091584 (N-Acetylleucine)
CC(C)C[C@H](NC(C)=O)C(O)=O
Download
INCHI for NP0091584 (N-Acetylleucine)
InChI=1S/C8H15NO3/c1-5(2)4-7(8(11)12)9-6(3)10/h5,7H,4H2,1-3H3,(H,9,10)(H,11,12)/t7-/m0/s1
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View in JSmol
Synonyms
ValueSource
AcetylleucineChEBI
N-Acetyl-leuChEBI
Acetyl-L-leucineHMDB
N-Acetyl-L-leucinHMDB
N-Acetyl-L-leucineHMDB
TanganilHMDB
LasdolHMDB
Acetyl-DL-leucineHMDB
N-AcetylleucineChEBI
Chemical FormulaC8H15NO3
Average Mass173.2096 Da
Monoisotopic Mass173.10519 Da
IUPAC Name(2S)-2-acetamido-4-methylpentanoic acid
Traditional NameN-acetyl-leu
CAS Registry NumberNot Available
SMILES
CC(C)C[C@H](NC(C)=O)C(O)=O
InChI Identifier
InChI=1S/C8H15NO3/c1-5(2)4-7(8(11)12)9-6(3)10/h5,7H,4H2,1-3H3,(H,9,10)(H,11,12)/t7-/m0/s1
InChI KeyWXNXCEHXYPACJF-ZETCQYMHSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Apis ceranaLOTUS Database
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
Mus musculusLOTUS Database
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 leucine and derivatives. Leucine and derivatives are compounds containing leucine or a derivative thereof resulting from reaction of leucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentLeucine and derivatives  
Alternative Parents
Substituents
  • Leucine or derivatives
    • 

  • N-acyl-alpha-amino acid
    • 

  • N-acyl-alpha amino acid or derivatives
    • 

  • Branched fatty acid
    • 

  • Methyl-branched fatty acid
    • 

  • Fatty acid
    • 

  • Fatty acyl
    • 

  • Carboximidic acid
    • 

  • Carboximidic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Propargyl-type 1,3-dipolar organic compound
    • 

  • Organic 1,3-dipolar compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Organic oxide
    • 

  • Organic nitrogen compound
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.78ALOGPS
logP0.49ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)4.2ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity43.61 m³·mol⁻¹ChemAxon
Polarizability18.09 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0011756  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028426  
KNApSAcK IDNot Available
Chemspider ID64075  
KEGG Compound IDC02710  
BioCyc IDCPD-433  
BiGG IDNot Available
Wikipedia LinkAcetylleucine  
METLIN IDNot Available
PubChem Compound70912  
PDB IDNot Available
ChEBI ID17786  
Good Scents IDNot Available
References
General References
  1. Jellum E, Horn L, Thoresen O, Kvittingen EA, Stokke O: Urinary excretion of N-acetyl amino acids in patients with some inborn errors of amino acid metabolism. Scand J Clin Lab Invest Suppl. 1986;184:21-6. [PubMed:3473611  ] 
  2. Tsutsui H, Maeda T, Min JZ, Inagaki S, Higashi T, Kagawa Y, Toyo'oka T: Biomarker discovery in biological specimens (plasma, hair, liver and kidney) of diabetic mice based upon metabolite profiling using ultra-performance liquid chromatography with electrospray ionization time-of-flight mass spectrometry. Clin Chim Acta. 2011 May 12;412(11-12):861-72. doi: 10.1016/j.cca.2010.12.023. Epub 2010 Dec 24. [PubMed:21185819  ] 
  3. Zhao YY, Liu J, Cheng XL, Bai X, Lin RC: Urinary metabonomics study on biochemical changes in an experimental model of chronic renal failure by adenine based on UPLC Q-TOF/MS. Clin Chim Acta. 2012 Mar 22;413(5-6):642-9. doi: 10.1016/j.cca.2011.12.014. Epub  2011 Dec 24. [PubMed:22227165  ]