NP-MRD: Showing NP-Card for {[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}acetic acid (NP0315897)

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Record Information

Version

1.0

Created at

2022-09-11 14:45:43 UTC

Updated at

2022-09-11 14:45:43 UTC

NP-MRD ID

NP0315897

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}acetic acid

Description

Ile-Gly, also known as isoleucyl-glycine or IG, 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. Ile-Gly is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. {[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}acetic acid is found in Trypanosoma brucei. It was first documented in 2022 (PMID: 35969667). Based on a literature review a significant number of articles have been published on Ile-Gly (PMID: 35407334) (PMID: 35260726) (PMID: 35623273) (PMID: 35364289).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 28  0  0  0  0  0  0  0  0999 V2000
   -2.7787    0.0533    1.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6491    0.9509    0.6548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0900    0.7204   -0.7092 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0976    0.9116   -1.8101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3987   -0.5907   -0.8913 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2587   -1.7267   -0.6539 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8919   -0.6651   -0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6132   -1.8579   -0.2783 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2995    0.3356    0.4890 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5198    0.4170    1.2283 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7156    0.1071    0.4411 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6264   -0.1974   -0.7692 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9672    0.1455    1.0225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1592   -0.5702    0.1918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6213    0.6783    1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5032   -0.6343    1.8510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8322    0.8547    1.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9809    2.0291    0.6875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3037    1.5164   -0.8706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1834    1.9825   -2.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1149    0.5835   -1.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7582    0.3633   -2.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1364   -0.6495   -1.9904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2125   -1.9955    0.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8494   -2.5333   -1.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6047   -2.3775   -1.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5251   -0.2497    2.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5729    1.4613    1.6540 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5917    0.9374    0.9889 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  1  0
  7  9  2  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  6
  4 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  6
  6 24  1  0
  6 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 13 29  1  0
M  END


  Mrv1652309112216452D          

 13 12  0  0  1  0            999 V2000
    3.3000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    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
   -1.6500   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 O   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
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  4  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0315897

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)[C@H](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)/t5-,7-/m0/s1

> <INCHI_KEY>
UCGDDTHMMVWVMV-FSPLSTOPSA-N

> <FORMULA>
C8H16N2O3

> <MOLECULAR_WEIGHT>
188.227

> <EXACT_MASS>
188.116092383

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
19.869800273758038

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[(2S,3S)-2-amino-1-hydroxy-3-methylpentylidene]amino}acetic acid

> <JCHEM_LOGP>
-1.9894590406662969

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.54637003707183

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5684501164755997

> <JCHEM_PKA_STRONGEST_BASIC>
9.673220511969289

> <JCHEM_POLAR_SURFACE_AREA>
95.91000000000001

> <JCHEM_REFRACTIVITY>
47.41910000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
{[(2S,3S)-2-amino-1-hydroxy-3-methylpentylidene]amino}acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       6.160   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.620   0.000   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  N   UNK     0       1.540   2.667   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.080  -2.667   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -3.080   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   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

View in JSmol

Synonyms

Value	Source
IG	ChEBI
Isoleucyl-glycine	ChEBI
Isoleucylglycine	ChEBI
L-Ile-gly	ChEBI

Chemical Formula

C₈H₁₆N₂O₃

Average Mass

188.2270 Da

Monoisotopic Mass

188.11609 Da

IUPAC Name

2-{[(2S,3S)-2-amino-1-hydroxy-3-methylpentylidene]amino}acetic acid

Traditional Name

{[(2S,3S)-2-amino-1-hydroxy-3-methylpentylidene]amino}acetic acid

CAS Registry Number

Not Available

SMILES

CC[C@H](C)[C@H](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)/t5-,7-/m0/s1

InChI Key

UCGDDTHMMVWVMV-FSPLSTOPSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Trypanosoma brucei	LOTUS Database	35616633

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dipeptide (CHEBI:74066 )

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	ChemAxon
pKa (Strongest Acidic)	3.57	ChemAxon
pKa (Strongest Basic)	9.67	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	19.87 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5360987

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6992868

PDB ID

Not Available

ChEBI ID

74066

Good Scents ID

Not Available

References

General References

Hojo K, Manabe Y, Uda T, Tsuda Y: Water-Based Solid-Phase Peptide Synthesis without Hydroxy Side Chain Protection. J Org Chem. 2022 Sep 2;87(17):11362-11368. doi: 10.1021/acs.joc.2c00828. Epub 2022 Aug 15. [PubMed:35969667 ]
Schieber R, Mas-Moruno C, Lasserre F, Roa JJ, Ginebra MP, Mucklich F, Pegueroles M: Effectiveness of Direct Laser Interference Patterning and Peptide Immobilization on Endothelial Cell Migration for Cardio-Vascular Applications: An In Vitro Study. Nanomaterials (Basel). 2022 Apr 5;12(7). pii: nano12071217. doi: 10.3390/nano12071217. [PubMed:35407334 ]
Alharthi S, Ali A, Iqbal M, Ibrar A, Ahmad B, Nisa S, Mabood F: Preparation of mixed-mode stationary phase for separation of peptides and proteins in high performance liquid chromatography. Sci Rep. 2022 Mar 8;12(1):4061. doi: 10.1038/s41598-022-08074-7. [PubMed:35260726 ]
Wang W, He Y, Gao Y, Gao H, Deng L, Gui Q, Cao Z, Yin Y, Feng Z: A peptide aptamer based electrochemical amperometric sensor for sensitive L-glutamate detection. Bioelectrochemistry. 2022 Aug;146:108165. doi: 10.1016/j.bioelechem.2022.108165. Epub 2022 May 18. [PubMed:35623273 ]
Umemura M, Kuriiwa K, Viet Dao L: Tandem repeats in precursor protein stabilize transcript levels and production levels of the fungal ribosomally synthesized and post-translationally modified peptide ustiloxin B. Fungal Genet Biol. 2022 May;160:103691. doi: 10.1016/j.fgb.2022.103691. Epub 2022 Mar 29. [PubMed:35364289 ]
LOTUS database [Link]

Showing NP-Card for {[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}acetic acid (NP0315897)

MOL for NP0315897 ({[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}acetic acid)

3D MOL for NP0315897 ({[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}acetic acid)

3D SDF for NP0315897 ({[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}acetic acid)

3D-SDF for NP0315897 ({[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}acetic acid)

PDB for NP0315897 ({[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}acetic acid)

3D PDB for NP0315897 ({[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}acetic acid)

SMILES for NP0315897 ({[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}acetic acid)

INCHI for NP0315897 ({[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}acetic acid)

Structure for NP0315897 ({[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}acetic acid)

3D Structure for NP0315897 ({[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}acetic acid)