NP-MRD: Showing NP-Card for Glycyl-Isoleucine (NP0123015)

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Record Information

Version

2.0

Created at

2022-05-12 09:17:22 UTC

Updated at

2022-05-12 09:17:22 UTC

NP-MRD ID

NP0123015

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glycyl-Isoleucine

Description

Glycyl-Isoleucine, also known as g-i dipeptide or gly-ile, 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. Glycyl-Isoleucine is a very strong basic compound (based on its pKa). It is an incomplete breakdown product of protein digestion or protein catabolism. 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. Glycyl-Isoleucine is a dipeptide composed of glycine and isoleucine. Glycyl-Isoleucine was first documented in 1981 (PMID: 17794841). This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an 'Expected' metabolite (PMID: 15950528) (PMID: 2503685).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 28  0  0  0  0  0  0  0  0999 V2000
    3.4036   -0.0743    0.8448 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6202    0.8775   -0.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1486    0.8989    0.2224 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6053    1.9936   -0.7550 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3786   -0.3129   -0.1976 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0290    0.0110    0.1596 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9816   -0.6373   -0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6906   -1.6102   -1.3816 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3799   -0.3381   -0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4556    0.6914    0.8932 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6770   -1.5768    0.4397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6585   -2.2749    0.1089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1358   -2.0510    1.4528 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2671    0.4737    1.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9244   -0.8584    0.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8347   -0.4789    1.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8682    0.7240   -1.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0440    1.9105    0.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8763    1.2804    1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9953    1.7707   -1.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8965    2.9823   -0.3985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5012    1.9084   -0.8042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3959   -0.3410   -1.3091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2552   -2.4620   -1.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9177   -1.2672    0.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8866    0.0343   -1.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3170    1.2728    0.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3149    0.3070    1.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7290   -2.8533    1.3978 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
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  5 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
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 13 29  1  0
M  END


  Mrv1652304032019092D          

 13 12  0  0  0  0            999 V2000
    0.5230   -0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    3.6020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  7  1  0  0  0  0
  9  4  1  0  0  0  0
 10  6  2  0  0  0  0
 10  7  1  4  0  0  0
 11  6  1  0  0  0  0
 12  8  2  0  0  0  0
 13  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0123015

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
KGVHCTWYMPWEGN-UHFFFAOYSA-N

> <FORMULA>
C8H16N2O3

> <MOLECULAR_WEIGHT>
188.2242

> <EXACT_MASS>
188.116092388

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
19.753804160527107

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2-amino-1-hydroxyethylidene)amino]-3-methylpentanoic acid

> <ALOGPS_LOGP>
-2.24

> <JCHEM_LOGP>
-2.0086889375763533

> <ALOGPS_LOGS>
-1.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.55170403397639

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.701901411225675

> <JCHEM_PKA_STRONGEST_BASIC>
9.334340809334764

> <JCHEM_POLAR_SURFACE_AREA>
95.91000000000001

> <JCHEM_REFRACTIVITY>
47.4191

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.70e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2-amino-1-hydroxyethylidene)amino]-3-methylpentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-APR-20         0                                  
HETATM    1  C   UNK     0       0.976  -0.976   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310  -0.206   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.977   5.954   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.977   4.414   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       3.644   6.724   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       3.644   3.644   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       6.311   3.644   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.977  -0.206   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    5                                                            
CONECT    3    1    5                                                       
CONECT    4    6    9                                                       
CONECT    5    2    3    7                                                  
CONECT    6    4   10   11                                                  
CONECT    7    5    8   10                                                  
CONECT    8    7   12   13                                                  
CONECT    9    4                                                            
CONECT   10    6    7                                                       
CONECT   11    6                                                            
CONECT   12    8                                                            
CONECT   13    8                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

View in JSmol

Synonyms

Value	Source
g-I dipeptide	HMDB
GI dipeptide	HMDB
Gly-ile	HMDB
Glycine isoleucine dipeptide	HMDB
Glycine-isoleucine dipeptide	HMDB
Glycylisoleucine	HMDB
L-Glycyl-L-isoleucine	HMDB
2-[(2-Amino-1-hydroxyethylidene)amino]-3-methylpentanoate	Generator

Chemical Formula

C₈H₁₆N₂O₃

Average Mass

188.2242 Da

Monoisotopic Mass

188.11609 Da

IUPAC Name

2-[(2-amino-1-hydroxyethylidene)amino]-3-methylpentanoic acid

Traditional Name

2-[(2-amino-1-hydroxyethylidene)amino]-3-methylpentanoic acid

CAS Registry Number

Not Available

SMILES

CCC(C)C(N=C(O)CN)C(O)=O

InChI Identifier

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

InChI Key

KGVHCTWYMPWEGN-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not 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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

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
Branched fatty acid
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Amino acid or derivatives
Carboxamide group
Amino acid
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Carboxylic acid
Organonitrogen compound
Organic oxygen compound
Organic oxide
Primary aliphatic amine
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Organooxygen compound
Primary amine
Amine
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.2	ALOGPS
logP	-2	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	3.7	ChemAxon
pKa (Strongest Basic)	9.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.91 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	47.42 m³·mol⁻¹	ChemAxon
Polarizability	19.75 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0028844

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

259613

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nath M, Pokharia S, Eng G, Song X, Kumar A: New triorganotin (IV) derivatives of dipeptides as models for metal-protein interactions: synthesis, structural characterization and biological studies. Spectrochim Acta A Mol Biomol Spectrosc. 2006 Jan;63(1):66-75. doi: 10.1016/j.saa.2005.04.038. Epub 2005 Jun 9. [PubMed:15950528 ]
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 ]
Steininger R, Karner J, Roth E, Langer K: Infusion of dipeptides as nutritional substrates for glutamine, tyrosine, and branched-chain amino acids in patients with acute pancreatitis. Metabolism. 1989 Aug;38(8 Suppl 1):78-81. doi: 10.1016/0026-0495(89)90147-9. [PubMed:2503685 ]

Showing NP-Card for Glycyl-Isoleucine (NP0123015)

MOL for NP0123015 (Glycyl-Isoleucine)

3D MOL for NP0123015 (Glycyl-Isoleucine)

3D SDF for NP0123015 (Glycyl-Isoleucine)

3D-SDF for NP0123015 (Glycyl-Isoleucine)

PDB for NP0123015 (Glycyl-Isoleucine)

3D PDB for NP0123015 (Glycyl-Isoleucine)

SMILES for NP0123015 (Glycyl-Isoleucine)

INCHI for NP0123015 (Glycyl-Isoleucine)

Structure for NP0123015 (Glycyl-Isoleucine)

3D Structure for NP0123015 (Glycyl-Isoleucine)