Glycyl-l-histidyl-l-lysine
- Iupac Name：(2S)-6-amino-2-[[(2S)-2-[(2-aminoacetyl)amino]-3-(1H-imidazol-5-yl)propanoyl]amino]hexanoic acid
- CAS No.: 49557-75-7
- Molecular Weight：340.384
- Modify Date.: 2022-11-22 19:55
- Introduction:
ChEBI: A tripeptide composed of glycine, L-histidine and L-lysine residues joined in sequence.
Gly-His-Lys is a tripeptide composed of glycine, L-histidine and L-lysine residues joined in sequence. It has a role as a metabolite, a chelator, a vulnerary and a hepatoprotective agent.|Prezatide is a tripeptide consisting of glycine, histidine, and lysine which readily forms a complex with copper ions. Prezatide is used in cosmetic products for the skin and hair. It is known to aid wound healing and its potential applications in chronic obstructive pulmonary disease and metastatic colon cancer are currently being investigated.
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1. Names and Identifiers
- 1.1 Name
- Glycyl-l-histidyl-l-lysine
- 1.2 Synonyms
(Gly-His-Lys)2Cu.xHAc Ahk-cu Copper Peptide Copper Peptide (GHK-Cu) Copper Peptide powder (GHK-cu) ghk GHK Cu Copper Peptide GHK Cu Copper Peptide GHK.Cu GHK-Cu GHKcu/Growth-Modulating peptide glycyl-histidyl-lysine Gly-His-Lys-Cu Gly-L-His-L-Lys Growth-modulating peptide H-Gly-His-Lys-OH Liver cell growth factor Liver Cell Growth Factor(GHK) Liver growth factor L-Lysine, glycyl-L-histidyl- L-Lysine,glycyl-L-histidyl-
- 1.3 CAS No.
- 49557-75-7
- 1.4 CID
- 73587
- 1.5 EINECS(EC#)
- 1592732-453-0
- 1.6 Molecular Formula
- C14H24N6O4 (isomer)
- 1.7 Inchi
- InChI=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
- 1.8 InChkey
- MVORZMQFXBLMHM-QWRGUYRKSA-N
- 1.9 Canonical Smiles
- C1=C(NC=N1)CC(C(=O)NC(CCCCN)C(=O)O)NC(=O)CN
- 1.10 Isomers Smiles
- C1=C(NC=N1)C[C@@H](C(=O)N[C@@H](CCCCN)C(=O)O)NC(=O)CN
2. Properties
- 2.1 Density
- 1.324
- 2.1 Boiling point
- 831 °C at 760 mmHg
- 2.1 Refractive index
- 1.582
- 2.1 Flash Point
- 456.4 °C
- 2.1 Precise Quality
- 340.18600
- 2.1 PSA
- 176.22000
- 2.1 logP
- 0.27650
- 2.1 Appearance
- White powder
- 2.2 pKa
- 3.11±0.10(Predicted)
- 2.3 StorageTemp
- Keep in dark place,Inert atmosphere,2-8°C
3. Use and Manufacturing
- 3.1 Definition
- ChEBI: A tripeptide composed of glycine, L-histidine and L-lysine residues joined in sequence.
- 3.2 Usage
- anti-wrikle
4. Safety and Handling
- 4.1 Specification
-
The L-Lysine,glycyl-L-histidyl-, with the CAS registry number 49557-75-7, has the systematic name of glycyl-L-histidyl-L-lysine.
The physical properties of this chemical are as follows: (1)ACD/LogP: -2.24; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): -6.61; (4)ACD/LogD (pH 7.4): -5.23; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 10; (10)#H bond donors: 8; (11)#Freely Rotating Bonds: 13; (12)Polar Surface Area: 91.22 ; (13)Index of Refraction: 1.582; (14)Molar Refractivity: 85.82 cm3; (15)Molar Volume: 256.9 cm3; (16)Polarizability: 34.02×10-24 cm3; (17)Surface Tension: 67.4 dyne/cm; (18)Density: 1.324 g/cm3; (19)Flash Point: 456.4 °C; (20)Enthalpy of Vaporization: 126.59 kJ/mol; (21)Boiling Point: 831 °C at 760 mmHg; (22)Vapour Pressure: 2.86E-29 mmHg at 25°C.
Additionally, you could obtain the molecular structure by converting the following datas:
(1)SMILES:O=C(O)[C@@H](NC(=O)[C@@H](NC(=O)CN)Cc1cncn1)CCCCN
(2)InChI:InChI=1/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
(3)InChIKey:MVORZMQFXBLMHM-QWRGUYRKBM
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
no data available
2.2 GHS label elements, including precautionary statements
| Pictogram(s) | no data available |
| Signal word | no data available |
| Hazard statement(s) | no data available |
| Precautionary statement(s) | |
| Prevention | no data available |
| Response | no data available |
| Storage | no data available |
| Disposal | no data available |
2.3 Other hazards which do not result in classification
no data available
6. Synthesis Route
49557-75-7Total: 1 Synthesis Route
8. Other Information
- 8.0 Absorption
- Prezatide both free and in complex with copper can pass through the stratum corneum. Its absorption is pH dependent with the highest absorption occurring at physiological pH.
- 8.1 Metabolism
- Prezatide is broken down to histidyl-lysine which is likely further degraded to other metabolites of proteolysis.
- 8.2 Biological Half Life
- Prezatide is rapidly eliminated within minutes.
- 8.3 Mesh Entry Terms
- copper glycyl-histidyl-lysine
- 8.4 Description
- Copper peptide GHK-Cu is a naturally occurring copper complex of the tripeptide glycyl-L-histidyl-L-lysine. The tripeptide has strong affinity for copper(II) and was first isolated from human plasma. It can be found also in saliva and urine.
- 8.5 Uses
- Glycyl-L-histidyl-L-lysine is a liver cell growth factor and an asynthetic hepatotrophic agent that stimulates hepatic erythropoietic factor production.
- 8.6 Uses
- anti-wrikle
- 8.7 Definition
- ChEBI: A tripeptide composed of glycine, L-histidine and L-lysine residues joined in sequence.
- 8.8 Pharmaceutical Applications
- Glycyl-l-histidyl-l-lysine (GHK) is a tripeptide known for its high binding affinity to Cu2+ and its complex role in wound healing. The GHK–Cu(II) complex was isolated from human plasma in the 1970s and it was shown to be an activator for wound healing. GHK–Cu(II) has two main functions: as an anti-inflammatory agent to protect the tissue from oxidative damage after the injury, and as an activator for wound healing itself as it activates the tissue remodelling.
The structure of GHK is very similar to that of common drugs used to treat ulcers.
After the initial stages of wound healing are activated, such as blood coagulation and neutrophil invasion, a second stage of wound healing begins, which includes the population of GHK at the wound, which has a high affinity to Cu2+. Mast cells, which are located in the skin, secrete GHK, which accumulates Cu2+ and forms the copper complex GHK–Cu(II) and therefore increases the metal–tripeptide concentration at the wound. First, GHK–Cu(II) has an anti-inflammatory effect by protecting the tissue from oxidative damage and by suppressing local inflammatory signals (i.e. cytokine interleukin-1 (IL-1)). Second, GHK–Cu(II) is released into the blood stream and encourages the production of wound macrophages that support the wound repair by removing the damaged tissue and secreting a family of several growth factor proteins. GHK–Cu(II) also hinders fibroblast production of TGF-β-1 and therefore suppresses the scar development. The GHK–Cu(II) complex also stimulates the growth of blood vessels, neurons and elastin, and, in general, supports most processes of wound healing.
9. Computational chemical data
- Molecular Weight: 340.384g/mol
- Molecular Formula: C14H24N6O4
- Compound Is Canonicalized: True
- XLogP3-AA: -4.4
- Exact Mass: 340.18590327
- Monoisotopic Mass: 340.18590327
- Complexity: 434
- Rotatable Bond Count: 11
- Hydrogen Bond Donor Count: 6
- Hydrogen Bond Acceptor Count: 7
- Topological Polar Surface Area: 176
- Heavy Atom Count: 24
- Defined Atom Stereocenter Count: 2
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADceBzuAAAAAAAAAAAAAAAAAAAAWAAAAAAAAAAAAAAAAABgAAAHgAQCAAACCjBlgQtmBbJkgCoARX3fAAAgC2xEqABUYG4cAiCaBJA2SGUQAAMlgLQQCGcSQAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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