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Showing NP-Card for Isoleucyl-Glycine (NP0136516)

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Record Information
Version2.0
Created at2022-05-12 15:16:33 UTC
Updated at2022-05-12 15:16:33 UTC
NP-MRD IDNP0136516
Secondary Accession NumbersNone
Natural Product Identification
Common NameIsoleucyl-Glycine
DescriptionIsoleucyl-Glycine, also known as i-g dipeptide or ile-gly, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Isoleucyl-Glycine is a very strong basic compound (based on its pKa). Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. It is an incomplete breakdown product of protein digestion or protein catabolism. Isoleucyl-Glycine is a dipeptide composed of isoleucine and glycine. Isoleucyl-Glycine was first documented in 1971 (PMID: 4943789). This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an 'Expected' metabolite (PMID: 17794841) (PMID: 10563776).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0136516 (Isoleucyl-Glycine)


  Mrv1652304062013522D          

 13 12  0  0  0  0            999 V2000
    6.5704    2.1434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    1.3184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
Download

3D MOL for NP0136516 (Isoleucyl-Glycine)

     RDKit          3D

 29 28  0  0  0  0  0  0  0  0999 V2000
   -2.7303    1.0293    1.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8453   -0.1205    0.5356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1539    0.3370   -0.7046 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2129    0.6804   -1.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2448   -0.6866   -1.3127 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9241   -1.8947   -1.6917 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9187   -1.0253   -0.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1916   -2.2047   -0.2205 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7489   -0.0075    0.0037 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9231   -0.3257    0.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5834    0.9308    1.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1529    2.0400    0.8182 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7282    0.9062    1.9782 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1825    1.9628    0.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7081    0.9941    0.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8870    0.9134    2.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0982   -0.2699    1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4724   -1.0043    0.3898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5816    1.2545   -0.4943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6626    1.1432   -2.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9530    1.3979   -1.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6695   -0.2774   -2.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1296   -0.2320   -2.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6882   -2.6751   -1.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8800   -2.1101   -2.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5188    0.9886   -0.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5617   -0.9715    0.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6407   -0.9455    1.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7967    0.1726    2.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 13  1  0
 11 12  2  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  2 18  1  0
  3 19  1  1
  4 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  6
  6 24  1  0
  6 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 13 29  1  0
M  END
Download

3D SDF for NP0136516 (Isoleucyl-Glycine)


  Mrv1652304062013522D          

 13 12  0  0  0  0            999 V2000
    6.5704    2.1434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    1.3184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0136516

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C(N)C(=O)NCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H16N2O3/c1-3-5(2)7(9)8(13)10-4-6(11)12/h5,7H,3-4,9H2,1-2H3,(H,10,13)(H,11,12)

> <INCHI_KEY>
UCGDDTHMMVWVMV-UHFFFAOYSA-N

> <FORMULA>
C8H16N2O3

> <MOLECULAR_WEIGHT>
188.2242

> <EXACT_MASS>
188.116092388

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
19.686463435855515

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(2-amino-3-methylpentanamido)acetic acid

> <ALOGPS_LOGP>
-1.66

> <JCHEM_LOGP>
-2.616773262988892

> <ALOGPS_LOGS>
-1.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.567056418437591

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9431432246843214

> <JCHEM_PKA_STRONGEST_BASIC>
8.5069601358564

> <JCHEM_POLAR_SURFACE_AREA>
92.42000000000002

> <JCHEM_REFRACTIVITY>
46.8974

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.48e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-amino-3-methylpentanamido)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0136516 (Isoleucyl-Glycine)

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PDB for NP0136516 (Isoleucyl-Glycine)
HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  N   UNK     0      12.265   4.001   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      10.931   6.311   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       9.597   2.461   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.264   6.311   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      14.932   2.461   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8                                                            
CONECT   10    1   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

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3D PDB for NP0136516 (Isoleucyl-Glycine)
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SMILES for NP0136516 (Isoleucyl-Glycine)
CCC(C)C(N)C(=O)NCC(O)=O
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INCHI for NP0136516 (Isoleucyl-Glycine)
InChI=1S/C8H16N2O3/c1-3-5(2)7(9)8(13)10-4-6(11)12/h5,7H,3-4,9H2,1-2H3,(H,10,13)(H,11,12)
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View in JSmol
Synonyms
ValueSource
I-g dipeptideHMDB
IG dipeptideHMDB
Ile-glyHMDB
Isoleucine glycine dipeptideHMDB
Isoleucine-glycine dipeptideHMDB
IsoleucylglycineHMDB
L-Isoleucyl-L-glycineHMDB
2-[(2-Amino-1-hydroxy-3-methylpentylidene)amino]acetateGenerator
Chemical FormulaC8H16N2O3
Average Mass188.2242 Da
Monoisotopic Mass188.11609 Da
IUPAC Name2-(2-amino-3-methylpentanamido)acetic acid
Traditional Name(2-amino-3-methylpentanamido)acetic acid
CAS Registry NumberNot Available
SMILES
CCC(C)C(N)C(=O)NCC(O)=O
InChI Identifier
InChI=1S/C8H16N2O3/c1-3-5(2)7(9)8(13)10-4-6(11)12/h5,7H,3-4,9H2,1-2H3,(H,10,13)(H,11,12)
InChI KeyUCGDDTHMMVWVMV-UHFFFAOYSA-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 OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentDipeptides  
Alternative Parents
Substituents
  • Alpha-dipeptide
    • 

  • Isoleucine or derivatives
    • 

  • N-acyl-alpha-amino acid
    • 

  • N-acyl-alpha amino acid or derivatives
    • 

  • Alpha-amino acid amide
    • 

  • Alpha-amino acid or derivatives
    • 

  • Fatty amide
    • 

  • N-acyl-amine
    • 

  • Fatty acyl
    • 

  • Amino acid or derivatives
    • 

  • Carboxamide group
    • 

  • Amino acid
    • 

  • Secondary carboxylic acid amide
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Primary aliphatic amine
    • 

  • Organopnictogen compound
    • 

  • Organic nitrogen compound
    • 

  • Carbonyl group
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Primary amine
    • 

  • Amine
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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
logP-1.7ALOGPS
logP-2.6ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.94ChemAxon
pKa (Strongest Basic)8.51ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.42 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity46.9 m³·mol⁻¹ChemAxon
Polarizability19.69 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0028907  
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 Compound342532  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Steinberg S, Bada JL: Diketopiperazine formation during investigations of amino Acid racemization in dipeptides. Science. 1981 Jul 31;213(4507):544-5. doi: 10.1126/science.213.4507.544. [PubMed:17794841  ] 
  2. Crapatureanu S, Serbanescu R, Brevitt SB, Kluger R: Molecular necklaces. Cross-linking hemoglobin with reagents containing covalently attached ligands. Bioconjug Chem. 1999 Nov-Dec;10(6):1058-67. doi: 10.1021/bc990067f. [PubMed:10563776  ] 
  3. Bollon AP, Magee PT: Involvement of threonine deaminase in multivalent repression of the isoleucine-valine pathway in Saccharomyces cerevisiae. Proc Natl Acad Sci U S A. 1971 Sep;68(9):2169-72. doi: 10.1073/pnas.68.9.2169. [PubMed:4943789  ]