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glycyl-L-histidyl-L-lysine

HCID 73587
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
49557-75-7
Standard SMILES
NCCCC[C@H](NC(=O)[C@H](Cc1cnc[nH]1)NC(=O)CN)C(=O)O
InChIKey
MVORZMQFXBLMHM-QWRGUYRKSA-N
Molecular formula
C14H24N6O4
Average molar mass
340.38 g/mol
Monoisotopic mass
340.18590327

Overview

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 hepatoprotective agent and a vulnerary.

Names & identifiers

Preferred name
glycyl-L-histidyl-L-lysine
IUPAC
(2S)-6-amino-2-[[(2S)-2-[(2-aminoacetyl)amino]-3-(1H-imidazol-5-yl)propanoyl]amino]hexanoic acid
English name
Copper Peptide
Molecular formula
C14H24N6O4
Molecular weight
340.38

Names & synonyms

glycyl-l-histidyl-l-lysine49557-75-7PrezatideLiver cell growth factorGlycyl-histidyl-lysineCopper(II)ghkKOLLAREN39TG2H631EPC-1020 FREE BASEORISTAR GHKGrowth-modulating peptide (human)DTXSID30197831
Show more names
Ahk-cuGHKCB0875341Tripeptide-1 CopperBlue copper peptideCooper PeptideGHK Cu Copper PeptideCu-GHKCopper Peptide AHK-Cu
NSC-379527N(2)-(N-Glycyl-L-histidyl)-L-lysineNatural Cedarwood OilRefChem:868497Seacall Natural Cedarwood OilDTXCID90120322Gly-his-lysL-Lysine, glycyl-L-histidyl-

Database identifiers

CAS
49557-75-7
PubChem CID
73587
DTXSID
DTXSID30197831
ChEMBL
CHEMBL1814493
ChEBI

Properties

Computed structural properties

XLogP
-4.4
Topological polar surface area
176 Ų
Hydrogen bond donors
6
Hydrogen bond acceptors
7
Rotatable bonds
11
Heavy atoms
24
Formal charge
0
Complexity
433

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
CosmeticsCosmetic ingredients (Tripeptide-1) -> CIR (Cosmetic Ingredient Review)

Physicochemical properties

Melting point
144 °C · >144°C (dec.)
Boiling point
831 · 831.0±65.0 °C(Predicted)
Density
1.324 · 1.324
storage temp.
2 · under inert gas (nitrogen or Argon) at 2–8 °C
solubility
Aqueous Acid (Slightly), DMSO (Slightly)
form
Solid
pka
3.11 · 3.11±0.10(Predicted)
color
Off-White
Sequence
Copper gly-his-lys
Stability
Hygroscopic
InChIKey
MVORZMQFXBLMHM-QWRGUYRKSA-N
SMILES
C(O)(=O)[C@H](CCCCN)NC(=O)[C@H](CC1N=CNC=1)NC(=O)CN

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Toxicology

Toxicity SummarySafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org

Safety data

Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H317-H319
Precautionary statements
P280-P305+P351+P338

Chemistry & industry

Pharmacology

Pharmacodynamics · 1 item

Prezatide in complex with copper improve skin elasticity, density, and firmness, reduces fine lines and wrinkles, reduces photodamage, increases keratinocyte proliferation. Prezatide also displays anti-oxidant and angiogenic effects and appears to modulate tissue remodeling in injury.

Mechanism of Action · 1 item

Prezatide in complex with copper increases the synthesis and deposition of type I collagen and glycosaminoglycan. It also increases the expression of matrix metalloproteinase-2 as well as tissue inhibitor of matrix metalloproteinases-1 and -2, suggesting that it plays a role in the modulation of tissue remodeling. It is thought that prezatide's antioxidant activity is due to its ability to supply copper for superoxide dismutase and its anti inflammatory ability due to the blockage the of iron (Fe2+) release during injury. Prezatide also increases angiogenesis to injury sites. The precise mechanisms of these effects are unknown. It is also unknown whether prezatide's effects are due to the action of the tripeptide itself or its ability to localize and transport copper. Prezatide is known to be bound by heparin and heparin sulfate

Biological Half-LifePrezatide is rapidly eliminated within minutes.
Metabolism/MetabolitesPrezatide is broken down to histidyl-lysine which is likely further degraded to other metabolites of proteolysis.
Absorption, Distribution and ExcretionPrezatide 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.

Uses & manufacturing

UsesCIR ingredient: Tripeptide-1
Applications · 4 items

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
CHEBI:75430
UNII
39TG2H631E
Nikkaji
J291.374G
EWG's Food Scores
1 · 1
FDA UNII
39 TG2H631E · 39TG2H631E
UNSPSC Code
12352209 · 12352209
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
317 · H317-H319
Precautionary statements
280 · P280-P305+P351+P338

DescriptionCopper 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.

UsesCopper Peptide(GHK-Cu) can be used as skin antiaging agents.

Usesanti-wrikle

UsesGlycyl-L-histidyl-L-lysine is a liver cell growth factor and an asynthetic hepatotrophic agent that stimulates hepatic erythropoietic factor production.

Upstream & downstream products

Upstream raw materials

Fmoc-His(Trt)-OHFmoc-Lys(Boc)-OHFmoc-Gly-OH

Suppliers100 total

珠海冀百康生物科技有限公司0756-6348118 13825639916 · [email protected]
深圳市迈思立生物科技有限公司15977887120 15977887120 · [email protected]
山东济肽生物科技有限公司18366132549 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
宁波亿诺化学品有限公司86-574-27787657 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
成都傲飞生物化学品有限责任公司+86-028-60911900 13540204019 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
China Kouting Group Limited+86 (21) 5811-6473 5811-6475 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
Creative Peptides[email protected]
合肥赛曼诺生物科技有限公司0551-65326643 18156095617 · [email protected]
深圳市健元医药科技有限公司+86-755-86350868 13651449654 · [email protected]
上海遐瑞医药科技有限公司+86 21 61551611
峨眉山鸿森生物医药股份有限公司0833-6186278 19162541913 · [email protected]
上海昶衍化工科技有限公司021-20242659 18930833303 · [email protected]
湖北威德利化学试剂有限公司186-02735115 18602735115 · [email protected]
四川爱元生物医药科技有限公司0838-6510595 13402890778 15102836436 · [email protected]
四川省维克奇生物科技有限公司028-81700200 18116577057 · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
四川安派博生物科技有限公司028-65294243 18682730901 · [email protected]
上海御略医药科技有限公司021-60345187 13671753212 · [email protected]
山东君泰药业有限公司15901008306 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
上海寰川实业有限公司021-61478794 · [email protected]
无锡亚肽生物科技有限公司0510-83583050 13771062561 · [email protected]
上海孚一生物科技有限公司+86 (21) 61124340
上海有吉医药化工有限公司021-50689757 15618953996 · [email protected]
湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
桦特昇生物科技(武汉)有限公司027-59207879 1972026995 18140587686 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
广东易肽生物科技有限公司13482530519; 13482530519 · [email protected]
上海昕凯医药科技有限公司21-619849051-1 18521059765 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
杭州鼎燕化工有限公司0571-87157530-8003 18049756717 · [email protected]
杭州固拓生物科技有限公司0571-88211921 17357109671 · [email protected]
上海德欣致远生物技术有限公司021-58088081 18317173152 · [email protected]
上海岚克医药科技发展有限公司0086-21-58956006
南京莱昂生物科技有限公司025-84523390 -127; 17705183659 · [email protected]
北京华威锐科化工科技有限公司89508211 18501085097 · [email protected]
成都云希化工有限公司+86-17380623303 · [email protected]
南京药诚医药科技有限公司025-57043319 15261831516 · [email protected]
无锡景耀生物科技有限公司88770633 13961738808 · [email protected]
上海前衍生物科技有限公司02781293128 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
成都麦迪森生物科技有限公司19981944287 · [email protected]
南京罗迈美生物科技有限公司[email protected]
上海超岚化工科技中心QQ:65489617 13301690235 · [email protected]
上海超岚化工科技中心(原上海巢莱)0-2022843681 15618226720 · [email protected]

Additional notes

DefinitionChEBI: 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.