Np mrd loader

Showing NP-Card for N-Acetylisoleucine (NP0333431)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2024-06-18 21:11:44 UTC
Updated at2024-09-03 04:22:28 UTC
NP-MRD IDNP0333431
Natural Product DOIhttps://doi.org/10.57994/2869
Secondary Accession NumbersNone
Natural Product Identification
Common NameN-Acetylisoleucine
DescriptionN-Acetylisoleucine belongs to the class of organic compounds known as isoleucine and derivatives. Isoleucine and derivatives are compounds containing isoleucine or a derivative thereof resulting from reaction of isoleucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-Acetylisoleucine is an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetylisoleucine was first documented in 1986 (PMID: 3473611). An N-acetyl-L-amino acid that is L-isoleucine in which one of the nitrogens attached to the nitrogen is replaced by an acetyl group.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0333431 (N-Acetylisoleucine)


  Mrv1652303081901252D          

 12 11  0  0  0  0            999 V2000
10000.3567 9999.5886    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.6428 9999.1751    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9285 9999.5886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2141 9999.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6428 9998.3502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.356710000.4124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.072310000.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.785810000.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.072310001.6497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0723 9999.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7858 9999.5886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0723 9998.3502    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  6  0  0  0
  1 10  1  0  0  0  0
  2  3  1  0  0  0  0
  2  5  1  1  0  0  0
  3  4  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
Download

3D MOL for NP0333431 (N-Acetylisoleucine)

Download
3D SDF for NP0333431 (N-Acetylisoleucine)

  Mrv1652303081901252D          

 12 11  0  0  0  0            999 V2000
10000.3567 9999.5886    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.6428 9999.1751    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9285 9999.5886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2141 9999.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6428 9998.3502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.356710000.4124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.072310000.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.785810000.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.072310001.6497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0723 9999.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7858 9999.5886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0723 9998.3502    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  6  0  0  0
  1 10  1  0  0  0  0
  2  3  1  0  0  0  0
  2  5  1  1  0  0  0
  3  4  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333431

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H15NO3/c1-4-5(2)7(8(11)12)9-6(3)10/h5,7H,4H2,1-3H3,(H,9,10)(H,11,12)/t5-,7-/m0/s1

> <INCHI_KEY>
JDTWZSUNGHMMJM-FSPLSTOPSA-N

> <FORMULA>
C8H15NO3

> <MOLECULAR_WEIGHT>
173.212

> <EXACT_MASS>
173.105193347

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.244875190253055

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S)-2-acetamido-3-methylpentanoic acid

> <ALOGPS_LOGP>
0.77

> <JCHEM_LOGP>
0.5721991746666668

> <ALOGPS_LOGS>
-0.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.560333915629815

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.198063315868436

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6342513751549141

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
43.5377

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.52e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S)-2-acetamido-3-methylpentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0333431 (N-Acetylisoleucine)
Download
PDB for NP0333431 (N-Acetylisoleucine)
HEADER    PROTEIN                                 08-MAR-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-MAR-19         0                                  
HETATM    1  C   UNK     0    8667.3338665.899   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8666.0008665.127   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8664.6678665.899   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8663.3338665.127   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8666.0008663.587   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0    8667.3338667.436   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0    8668.6688668.206   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8670.0008667.436   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8668.6688669.746   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8668.6688665.127   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8670.0008665.899   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8668.6688663.587   0.000  0.00  0.00           O+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2                                                            
CONECT    6    1    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    1   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

Download
3D PDB for NP0333431 (N-Acetylisoleucine)
Download
SMILES for NP0333431 (N-Acetylisoleucine)
CC[C@H](C)[C@H](NC(C)=O)C(O)=O
Download
INCHI for NP0333431 (N-Acetylisoleucine)
InChI=1S/C8H15NO3/c1-4-5(2)7(8(11)12)9-6(3)10/h5,7H,4H2,1-3H3,(H,9,10)(H,11,12)/t5-,7-/m0/s1
Download
View in JSmol
Synonyms
ValueSource
N-Acetyl-L-isoleucineHMDB
N-AcetylisoleucineHMDB
Chemical FormulaC8H15NO3
Average Mass173.2120 Da
Monoisotopic Mass173.10519 Da
IUPAC Name(2S,3S)-2-acetamido-3-methylpentanoic acid
Traditional Name(2S,3S)-2-acetamido-3-methylpentanoic acid
CAS Registry NumberNot Available
SMILES
CC[C@H](C)[C@H](NC(C)=O)C(O)=O
InChI Identifier
InChI=1S/C8H15NO3/c1-4-5(2)7(8(11)12)9-6(3)10/h5,7H,4H2,1-3H3,(H,9,10)(H,11,12)/t5-,7-/m0/s1
InChI KeyJDTWZSUNGHMMJM-FSPLSTOPSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, D2O, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-18View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, D2O, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-18View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, D2O, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-18View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-18View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-18View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600, D2O, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-18View Spectrum
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isoleucine and derivatives. Isoleucine and derivatives are compounds containing isoleucine or a derivative thereof resulting from reaction of isoleucine 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 ParentIsoleucine and derivatives  
Alternative Parents
Substituents
  • Isoleucine or derivatives
    • 

  • N-acyl-alpha-amino acid
    • 

  • N-acyl-alpha amino acid or derivatives
    • 

  • N-acyl-l-alpha-amino acid
    • 

  • Branched fatty acid
    • 

  • Methyl-branched fatty acid
    • 

  • Fatty acyl
    • 

  • Fatty acid
    • 

  • Acetamide
    • 

  • Carboxamide group
    • 

  • Secondary carboxylic acid amide
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organonitrogen compound
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • 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
logP0.77ALOGPS
logP0.57ChemAxon
logS-0.84ALOGPS
pKa (Strongest Acidic)4.2ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity43.54 m³·mol⁻¹ChemAxon
Polarizability18.24 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0061684  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7036275  
PDB IDNot Available
ChEBI ID21555  
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  ]