Glycyl-l-histidyl-l-lysine

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Glycyl-l-histidyl-l-lysine are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Glycyl-l-histidyl-l-lysine?

The molecule Glycyl-l-histidyl-l-lysine presents a molecular formula of C14H24N6O4 and its IUPAC name is (2S)-6-amino-2-[[(2S)-2-[(2-aminoacetyl)amino]-3-(1H-imidazol-5-yl)propanoyl]amino]hexanoic acid.

Glycyl-l-histidyl-l-lysine (GHL) is a tripeptide molecule consisting of the amino acids glycine, histidine, and lysine. It is a common peptide found in proteins and is known to be involved in a variety of biological processes. GHL has been shown to be an important component of the cell-signaling pathway known as the MAPK/ERK pathway. This pathway is important in the regulation of cell proliferation, cell differentiation, and cell death. GHL has also been shown to be involved in the regulation of cell migration and cell adhesion. In addition, GHL has been shown to be involved in the development of cancer..

3D structure

Cartesian coordinates

Geometry of Glycyl-l-histidyl-l-lysine in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Glycyl-l-histidyl-l-lysine MVORZMQFXBLMHM-QWRGUYRKSA-N chemical compound 2D structure molecule svg
Glycyl-l-histidyl-l-lysine

 

Molecule descriptors

 
IUPAC name(2S)-6-amino-2-[[(2S)-2-[(2-aminoacetyl)amino]-3-(1H-imidazol-5-yl)propanoyl]amino]hexanoic acid
InChI codeInChI=1S/C14H24N6O4/c15-4-2-1-3-10(14(23)24)20-13(22)11(19-12(21)6-16)5-9-7-17-8-18-9/h7-8,10-11H,1-6,15-16H2,(H,17,18)(H,19,21)(H,20,22)(H,23,24)/t10-,11-/m0/s1
InChI KeyMVORZMQFXBLMHM-QWRGUYRKSA-N
SMILESNCCCC[C@H](NC(=O)[C@H](Cc1cnc[nH]1)/N=C(\O)CN)C(=O)O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (2S)-6-amino-2-[(2S)-2-(2-aminoacetamido)-3-(1H-imidazol-5-yl)propanamido]hexanoic acid
  • (S)-6-Amino-2-((S)-2-(2-aminoacetamido)-3-(1H-imidazol-4-yl)propanamido)hexanoic acid
  • 39TG2H631E
  • 49557-75-7
  • 557G757
  • A871782
  • AC-31946
  • BDBM50350478
  • BG162807
  • C.P.P.
  • CS-0005654
  • Copper Peptide
  • Copper glycyl-histidyl-lysine
  • Copper(II)ghk
  • D92811
  • DB11296
  • DS-14630
  • GLY-HIS-LYS-OH
  • Gly-L-His-L-Lys
  • Gly-L-His-L-Lys-OH
  • Gly-his-lys
  • Glycyl-L-Histidyl-L-Lysine (H-Gly-L-His-L-Lys-OH)
  • Glycyl-histidyl-lysine
  • Glycyl-l-histidyl-l-lysine
  • Glycylhistidyllysine
  • Growth-modulating peptide (human)
  • HY-P0046
  • I10329
  • Iamin
  • KOLLAREN
  • L-Lysine, glycyl-L-histidyl-
  • Liver cell growth factor
  • MFCD00036754
  • N(2)-(N-Glycyl-L-histidyl)-L-lysine
  • NSC 379527
  • NSC-379527
  • ORISTAR GHK
  • PC-1020 FREE BASE
  • Prezatide
  • Tripeptide-1
  • ghk
  • glycyl-l-histidyl-l-lysine

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC13507674
  • UNII-39TG2H631E
  • AKOS016003505
  • DTXSID30197831
  • CHEMBL1814493
  • CHEBI:75430
  • SCHEMBL259085
  • SCHEMBL19087235

Physico-Chemical properties

IUPAC name(2S)-6-amino-2-[[(2S)-2-[(2-aminoacetyl)amino]-3-(1H-imidazol-5-yl)propanoyl]amino]hexanoic acid
Molecular formulaC14H24N6O4
Molecular weight340.378
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity87.07
LogP0.7
Topological polar surface area179.7

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.