3D Mol Similar

CYCLO(-LEU-PRO)

: Iupac Name：(3S,8aS)-3-(2-methylpropyl)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione; CAS No.: 2873-36-1; Molecular Weight：210.27; Modify Date.: 2023-11-05 10:09; Introduction: Sorbicillin analog. A bioactive secondary metabolites from terrestrial Streptomyces species TN262. View more+

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1. Names and Identifiers

: 1.1 Name; CYCLO(-LEU-PRO); 1.2 Synonyms; (3S,8aS)-2,3,6,7,8,8a-Hexahydro-3-(2-methylpropyl)pyrrolo[1,2-a]pyrazine-1,4-dione (3S,8aS)-3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione (3S,8aS)-Hexahydro-3-(2-methylpropyl)pyrrolo[1,2-a]pyrazine-1,4-dione (3S,8aS)-Octahydro-3-(2-methylpropyl)pyrrolo[1,2-a]pyrazine-1,4-dione (3S-trans)-Hexahydro-3-isobutylpyrrolo(1,2-a)pyrazine-1,4-dione (3S-trans)-hexahydro-3-isobutylpyrrolo[1,2-a]pyrazine-1,4-dione 2-a)pyrazine-1,4-dione,hexahydro-3-isobutyl-pyrrolo(stereoisomer 4-dione,hexahydro-3-(2-methylpropyl)-2-a)pyrazine-(3s-trans)-pyrrolo( cis-Cyclo(L-Leu-L-Pro) Cyclo(Leu-Pro) Cyclo(L-leucyl-L-prolyl) Cyclo(L-leucyl-L-prolyl-) Cyclo(L-Leu-L-Pro) Cyclo(L-Pro-L-Leu) Cyclo(L-prolyl-L-leucyl) Cyclo(Pro-Leu) Cyclo(proline-leucine) cyclo-l-leu-l-pro Cyclo-L-prolyl-L-leucine EINECS 220-710-6 Gancidin W gancidinw L-Leucyl-L-proline lactam L-Leucyl-L-prolyl lactam Maculosin 6 Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(2-methylpropyl)-, (3S,8aS)- Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(2-methylpropyl)-, (3S-trans)- Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-isobutyl-, stereoisomer; View all

1.3 CAS No.: 2873-36-1

1.4 CID: 7074739

1.5 EINECS(EC#): 220-710-6

1.6 Molecular Formula: C11H18N2O2 (isomer)

1.7 Inchi: InChI=1S/C11H18N2O2/c1-7(2)6-8-11(15)13-5-3-4-9(13)10(14)12-8/h7-9H,3-6H2,1-2H3,(H,12,14)/t8-,9-/m0/s1

1.8 InChIkey: SZJNCZMRZAUNQT-IUCAKERBSA-N

1.9 Canonical Smiles: [H][C@@]12CCCN1C(=O)[C@H](CC(C)C)NC2=O

1.10 Isomers Smiles: CC(C)C[C@H]1C(=O)N2CCC[C@H]2C(=O)N1

2. Properties

2.1 Density: 1.14

2.1 Melting point: 163-165℃

2.1 Boiling point: 427.6±34.0 °C(Predicted)

2.1 Refractive index: 1.529

2.1 Flash Point: 212.4°C

2.1 Precise Quality: 210.13700

2.1 PSA: 49.41000

2.1 logP: 0.78860

2.1 Appearance: Solid

2.2 Chemical Properties: White Solid

2.3 Color/Form: White to Off-White

2.4 pKa: 13.27±0.40(Predicted)

2.5 Water Solubility: Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)

2.6 StorageTemp: Inert atmosphere,2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A homodetic cyclic peptide composed from leucyl and prolyl residues. CYCLO(-LEU-PRO)Supplier

3.2 Usage: Sorbicillin analog. A bioactive secondary metabolites from terrestrial Streptomyces species TN262.

4. 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

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5. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

6. Synthesis Route

2873-36-1Total: 32 Synthesis Route

61-90-5 648 Suppliers

2873-36-1 14 Suppliers

Literatures:
Jhaumeer-Laulloo; Khodabocus; Jugoo; Jheengut; Sobha Journal of the Indian Chemical Society, 2003 , vol. 80, # 8 p. 765 - 768
Yield: ~%

147-85-3 620 Suppliers

2873-36-1 14 Suppliers

Literatures:
Jhaumeer-Laulloo; Khodabocus; Jugoo; Jheengut; Sobha Journal of the Indian Chemical Society, 2003 , vol. 80, # 8 p. 765 - 768
Yield: ~%

2743-60-4 4 Suppliers

2873-36-1 14 Suppliers

Literatures:
Jhaumeer-Laulloo; Khodabocus; Jugoo; Jheengut; Sobha Journal of the Indian Chemical Society, 2003 , vol. 80, # 8 p. 765 - 768
Yield: ~%

View all

7. Other Information

7.0 Description: Cyclo(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.

7.1 Chemical Properties: White Solid

7.2 Uses: Sorbicillin analog. A bioactive secondary metabolites from terrestrial Streptomyces species TN262.

7.3 Definition: ChEBI: A homodetic cyclic peptide composed from leucyl and prolyl residues.

8. Computational chemical data

Molecular Weight: 210.27g/mol
Molecular Formula: C₁₁H₁₈N₂O₂
Compound Is Canonicalized: True
XLogP3-AA: 1.1
Exact Mass: 210.136827821
Monoisotopic Mass: 210.136827821
Complexity: 288
Rotatable Bond Count: 2
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 49.4
Heavy Atom Count: 15
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: AAADceBzMAAAAAAAAAAAAAAAAAAAAWAAAAAsAAAAAAAAAFgAAAAAHgAQAAAADSjBgAQCAAPAAAAIAAEQEAAAAAAAAAAAAIGIAAAAQBIAgCAUAAAAFgCAAAAYAQAMAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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