Basic information
- CAS
2873-36-1- Standard SMILES
CC(C)C[C@@H]1NC(=O)[C@@H]2CCCN2C1=O- InChIKey
SZJNCZMRZAUNQT-IUCAKERBSA-N- Molecular formula
- C11H18N2O2
- Average molar mass
- 210.27 g/mol
- Monoisotopic mass
- 210.13682782
Overview
Cyclo(L-Leu-L-Pro) is a homodetic cyclic peptide composed from leucyl and prolyl residues. It has a role as a marine metabolite and a bacterial metabolite. It is a homodetic cyclic peptide, a dipeptide and a pyrrolopyrazine.
Names & identifiers
- Preferred name
- Gancidin W
- IUPAC
- (3S,8aS)-3-(2-methylpropyl)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
- English name
- Cyclo(-Leu-Pro)
- Molecular formula
- C11H18N2O2
- Molecular weight
- 210.27
Names & synonyms
Gancidin WCyclo-L-leu-L-proKQV8MY059BRefChem:922070220-710-62873-36-1Cyclo(-Leu-Pro)(3S,8aS)-3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dionecyclo(L-leu-L-pro)Cyclo(L-prolyl-L-leucyl)cyclo(Leu-Pro)Cyclo(L-leucyl-L-prolyl)
Show more names
Cyclo(proline-leucine)Cyclo(Pro-Leu)gancidinwc(Leu-Pro)Cyclo(L-Pro-D-Leu)Cyclo(L-Pro-L-Leu-)Cyclo-L-prolyl-L-leucine
Cyclo(L-Pro-L-Leu)Maculosin 6L-Leucyl-L-proline lactamMFCD00237617L-cyclo(Leucyloprolyl)L-cyclo(Leu-pro)L,L-Cyclo(leucylprolyl)Cyclo L-Pro-L-Leu (Fr. 1-6)
Database identifiers
- CAS
2873-36-1- PubChem CID
- 7074739
- DTXSID
DTXSID80951384- ChEMBL
CHEMBL508326- ChEBI
CHEBI:133094
Properties
Computed structural properties
- XLogP
- 1.1
- Topological polar surface area
- 49.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 288
Experimental & physicochemical properties
Melting Point168 - 172 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 163 · 163-165℃
- Boiling point
- 427.6 · 427.6±34.0 °C(Predicted)
- Density
- 1.14 · 1.14
- storage temp.
- 2 · Inert atmosphere,2-8°C
- solubility
- Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 13.27 · 13.27±0.40(Predicted)
- color
- White to Off-White
- FDA UNII
- 8 MY059B · KQV8MY059B
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H317
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Toxicity
- mouse,LD50,intravenous,80mg/kg (80mg/kg),"Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 2, Pg. 1354, 1978.
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H317
- Precautionary statements
- P280
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Applications
DescriptionCyclo(L-Leu-L-Pro) is a diketopiperazine metabolite that has been isolated from various bacterial and fungal species including Streptomyces. It is active against twelve strains of vancomycin-resistant enterococci (VRE) with MIC values of 12.5 μg/ml for E. faecalis strains K-99-34, K-00-184, and K-00-221. It also inhibits growth of K562, HL-60, and U937 leukemia cells in a concentration-dependent manner when used at concentrations of 1-500 μg/ml. Cyclo(L-Leu-L-Pro) also has antifouling activity, inhibiting attachment of B. amphitrite larva with an EC50 value of 0.15 mM.
UsesSorbicillin analog. A bioactive secondary metabolites from terrestrial Streptomyces species TN262.
Suppliers80 total
陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
毕佳索（上海毕得医药科技股份有限公司）400-6005915 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]
南京昱盛康生物科技有限公司13327808530 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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