NP-MRD: Showing NP-Card for (2s)-2-[(2-amino-1-hydroxyethylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid (NP0278270)

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Record Information

Version

1.0

Created at

2022-09-09 03:14:07 UTC

Updated at

2022-09-09 03:14:07 UTC

NP-MRD ID

NP0278270

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-[(2-amino-1-hydroxyethylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid

Description

Gly-His, also known as G-H or gly-L-his, 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. Gly-His 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)-2-[(2-amino-1-hydroxyethylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid is found in Trypanosoma brucei. It was first documented in 2022 (PMID: 36082494). Based on a literature review a significant number of articles have been published on Gly-His (PMID: 35984670) (PMID: 35792768) (PMID: 35648482) (PMID: 35589864) (PMID: 35493947) (PMID: 35325810).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092205142D          

 15 15  0  0  1  0            999 V2000
    1.2822    4.8268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    4.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    3.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    3.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    3.1768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.1143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    2.3518    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  4  0  0  0
  3  5  2  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  8 12  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0278270

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NCC(O)=N[C@@H](CC1=CN=CN1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H12N4O3/c9-2-7(13)12-6(8(14)15)1-5-3-10-4-11-5/h3-4,6H,1-2,9H2,(H,10,11)(H,12,13)(H,14,15)/t6-/m0/s1

> <INCHI_KEY>
YIWFXZNIBQBFHR-LURJTMIESA-N

> <FORMULA>
C8H12N4O3

> <MOLECULAR_WEIGHT>
212.209

> <EXACT_MASS>
212.090940262

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
20.111010350795585

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(2-amino-1-hydroxyethylidene)amino]-3-(1H-imidazol-5-yl)propanoic acid

> <JCHEM_LOGP>
-5.530833018726818

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
3.95618263254374

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.164802416387543

> <JCHEM_PKA_STRONGEST_BASIC>
9.335340907047094

> <JCHEM_POLAR_SURFACE_AREA>
124.58999999999999

> <JCHEM_REFRACTIVITY>
51.3842

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2-amino-1-hydroxyethylidene)amino]-3-(3H-imidazol-4-yl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  N   UNK     0       2.393   9.010   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       1.060   8.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.060   6.700   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.393   5.930   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      -0.274   5.930   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       1.830  -0.290   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -0.186   1.175   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -1.608   3.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.608   2.080   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -2.941   4.390   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                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    8                                                       
CONECT   13    6   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
(2S)-2-(2-Aminoacetamido)-3-(1H-imidazol-5-yl)propanoic acid	ChEBI
G-H	ChEBI
GH	ChEBI
Gly-L-his	ChEBI
Glycylhistidine	ChEBI
H-Gly-his-OH	ChEBI
(2S)-2-(2-Aminoacetamido)-3-(1H-imidazol-5-yl)propanoate	Generator

Chemical Formula

C₈H₁₂N₄O₃

Average Mass

212.2090 Da

Monoisotopic Mass

212.09094 Da

IUPAC Name

(2S)-2-[(2-amino-1-hydroxyethylidene)amino]-3-(1H-imidazol-5-yl)propanoic acid

Traditional Name

(2S)-2-[(2-amino-1-hydroxyethylidene)amino]-3-(3H-imidazol-4-yl)propanoic acid

CAS Registry Number

Not Available

SMILES

NCC(O)=N[C@@H](CC1=CN=CN1)C(O)=O

InChI Identifier

InChI=1S/C8H12N4O3/c9-2-7(13)12-6(8(14)15)1-5-3-10-4-11-5/h3-4,6H,1-2,9H2,(H,10,11)(H,12,13)(H,14,15)/t6-/m0/s1

InChI Key

YIWFXZNIBQBFHR-LURJTMIESA-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
Histidine or derivatives
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Imidazolyl carboxylic acid derivative
Azole
Imidazole
Heteroaromatic compound
Amino acid or derivatives
Carboxamide group
Carboxylic acid salt
Amino acid
Secondary carboxylic acid amide
Organoheterocyclic compound
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organic zwitterion
Primary aliphatic amine
Organic nitrogen compound
Organic oxide
Organic salt
Amine
Organic oxygen compound
Carbonyl group
Organopnictogen compound
Primary amine
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dipeptide (CHEBI:73515 )

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	-5.5	ChemAxon
pKa (Strongest Acidic)	3.16	ChemAxon
pKa (Strongest Basic)	9.34	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.59 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	51.38 m³·mol⁻¹	ChemAxon
Polarizability	20.11 Å³	ChemAxon
Number of Rings	1	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

5385970

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7023106

PDB ID

Not Available

ChEBI ID

73515

Good Scents ID

Not Available

References

General References

Zhou B, Sheng X, Xie H, Zhou S, Zhong M, Liu A: Inhibition of Alzheimer's Abeta1-42 Fibrillogenesis and Removal of Copper Ions by Polypeptides Modified Gold Nanoparticles. Chem Biodivers. 2022 Sep 9:e202200342. doi: 10.1002/cbdv.202200342. [PubMed:36082494 ]
Jensen KJ, Thygesen MB, Sorensen KK, Wu S, Treiberg T, Schoffelen S: Selective Acylation of Proteins at Gly and Lys in His Tags. Chembiochem. 2022 Aug 19:e202200359. doi: 10.1002/cbic.202200359. [PubMed:35984670 ]
Eylul Kiymaci M, Erdogan H, Bacanli M: Antioxidative, cytotoxic, and antibacterial properties of self-assembled glycine-histidine-based dipeptides with or without silver nanoparticles in bio-inspired film. Arh Hig Rada Toksikol. 2022 Jul 7;73(2):169-177. doi: 10.2478/aiht-2022-73-3658. [PubMed:35792768 ]
Marlin A, Hierlmeier I, Guillou A, Bartholoma M, Tripier R, Patinec V: Bioconjugated chelates based on (methylpyridinyl)tacn: synthesis, 64Cu labeling and in vitro evaluation for prostate cancer targeting. Metallomics. 2022 Jun 24;14(6). pii: 6596882. doi: 10.1093/mtomcs/mfac036. [PubMed:35648482 ]
Wang P, Xue S, Chen B, Liao F: A novel peptide-based fluorescent probe for highly selective detection of mercury (II) ions in real water samples and living cells based on aggregation-induced emission effect. Anal Bioanal Chem. 2022 Jul;414(16):4717-4726. doi: 10.1007/s00216-022-04094-4. Epub 2022 May 20. [PubMed:35589864 ]
Zhou J, Li Q, Wu W, Zhang X, Zuo Z, Lu Y, Zhao H, Wang Z: Discovery of Novel Drug Candidates for Alzheimer's Disease by Molecular Network Modeling. Front Aging Neurosci. 2022 Apr 15;14:850217. doi: 10.3389/fnagi.2022.850217. eCollection 2022. [PubMed:35493947 ]
Ma L, Grant C, Gallazzi F, Watkinson LD, Carmack TL, Embree MF, Smith CJ, Medvedev D, Cutler CS, Li Y, Wilbur DS, Hennkens HM, Jurisson SS: Development and biodistribution studies of (77)As-labeled trithiol RM2 bioconjugates for prostate cancer: Comparison of [(77)As]As-trithiol-Ser-Ser-RM2 vs. [(77)As]As-trithiol-Glu-Ser-RM2. Nucl Med Biol. 2022 May-Jun;108-109:61-69. doi: 10.1016/j.nucmedbio.2022.03.003. Epub 2022 Mar 16. [PubMed:35325810 ]
Xian J, Parthasarathy S, Ruggiero SM, Balagura G, Fitch E, Helbig K, Gan J, Ganesan S, Kaufman MC, Ellis CA, Lewis-Smith D, Galer P, Cunningham K, O'Brien M, Cosico M, Baker K, Darling A, Veiga de Goes F, El Achkar CM, Doering JH, Furia F, Garcia-Cazorla A, Gardella E, Geertjens L, Klein C, Kolesnik-Taylor A, Lammertse H, Lee J, Mackie A, Misra-Isrie M, Olson H, Sexton E, Sheidley B, Smith L, Sotero L, Stamberger H, Syrbe S, Thalwitzer KM, van Berkel A, van Haelst M, Yuskaitis C, Weckhuysen S, Prosser B, Son Rigby C, Demarest S, Pierce S, Zhang Y, Moller RS, Bruining H, Poduri A, Zara F, Verhage M, Striano P, Helbig I: Assessing the landscape of STXBP1-related disorders in 534 individuals. Brain. 2022 Jun 3;145(5):1668-1683. doi: 10.1093/brain/awab327. [PubMed:35190816 ]
Wang L, Wang X, Lv X, Jin Q, Shang H, Wang CC, Wang L: The extracellular Ero1alpha/PDI electron transport system regulates platelet function by increasing glutathione reduction potential. Redox Biol. 2022 Apr;50:102244. doi: 10.1016/j.redox.2022.102244. Epub 2022 Jan 20. [PubMed:35077997 ]
Wang P, Wang Q, Guo Z, Xue S, Chen B, Liu Y, Ren W, Yang X, Wen S: A bifunctional peptide-based fluorescent probe for ratiometric and "turn-on" detection of Zn(II) ions and its application in living cells. Spectrochim Acta A Mol Biomol Spectrosc. 2022 Mar 5;268:120653. doi: 10.1016/j.saa.2021.120653. Epub 2021 Nov 22. [PubMed:34838424 ]
LOTUS database [Link]

Showing NP-Card for (2s)-2-[(2-amino-1-hydroxyethylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid (NP0278270)

MOL for NP0278270 ((2s)-2-[(2-amino-1-hydroxyethylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid)

3D MOL for NP0278270 ((2s)-2-[(2-amino-1-hydroxyethylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid)

3D SDF for NP0278270 ((2s)-2-[(2-amino-1-hydroxyethylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid)

3D-SDF for NP0278270 ((2s)-2-[(2-amino-1-hydroxyethylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid)

PDB for NP0278270 ((2s)-2-[(2-amino-1-hydroxyethylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid)

3D PDB for NP0278270 ((2s)-2-[(2-amino-1-hydroxyethylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid)

SMILES for NP0278270 ((2s)-2-[(2-amino-1-hydroxyethylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid)

INCHI for NP0278270 ((2s)-2-[(2-amino-1-hydroxyethylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid)

Structure for NP0278270 ((2s)-2-[(2-amino-1-hydroxyethylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid)

3D Structure for NP0278270 ((2s)-2-[(2-amino-1-hydroxyethylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid)