| Identification | Back Directory | [Name]
Cyclo(L-Pro-L-Trp-) | [CAS]
38136-70-8 | [Synonyms]
Brevianamide F
Cyclo(-Trp-Pro)
Cyclo(L-Pro-L-Trp-)
Cyclo(L-Trp-L-Pro-)
Cyclo-L-tryptophyl-L-proline
(3S,8AS)-3-(1H-INDOL-3-YLMETHYL)HEXAHYDROPYRROLO[1,2-A]PYRAZINE-1,4-DIONE
(3S,8aα)-3β-(1H-Indole-3-ylmethyl)octahydropyrrolo[1,2-a]pyrazine-1,4-dione
Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(1H-indol-3-ylmethyl)-, (3S,8aS)-
(3S)-2,3,6,7,8,8aα-Hexahydro-3β-(1H-indol-3-ylmethyl)pyrrolo[1,2-a]pyrazine-1,4-dione | [Molecular Formula]
C16H17N3O2 | [MDL Number]
MFCD29917326 | [MOL File]
38136-70-8.mol | [Molecular Weight]
283.33 |
| Chemical Properties | Back Directory | [Melting point ]
165-167 °C | [Boiling point ]
633.2±48.0 °C(Predicted) | [density ]
1.37±0.1 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
13.20±0.40(Predicted) | [color ]
White to Off-White | [InChI]
InChI=1S/C16H17N3O2/c20-15-14-6-3-7-19(14)16(21)13(18-15)8-10-9-17-12-5-2-1-4-11(10)12/h1-2,4-5,9,13-14,17H,3,6-8H2,(H,18,20)/t13-,14-/m0/s1 | [InChIKey]
RYFZBPVMVYTEKZ-KBPBESRZSA-N | [SMILES]
[C@@]12([H])CCCN1C(=O)[C@H](CC1C3=C(NC=1)C=CC=C3)NC2=O |
| Hazard Information | Back Directory | [Description]
Brevianamide F is an alkaloid metabolite produced by various Streptomyces, Actinomycetes, and Aspergillus strains that has diverse biological activities.1,2,3 It inhibits growth of M. luteus and S. aureus in an inhibitory disc assay when used at a concentration of 30 μg/disc as well as the Bacille Calmette-Guerin M. bovis strain (MIC = 12.5 μg/ml).2,3 Brevianamide F has antifouling activity, inhibiting attachment of B. neritina larvae to PVC plates without inducing lethality (EC50 = 6.35 μg/ml; LC50 = >200 μg/ml in paint used to coat PVC plates).1 | [Uses]
Brevianamide F is used in the preparation, reactions, medicinal and cheical propreties of diketopiperazines as bioactive natural products. Acts as a reagent in the total synthesis and antitumor activity in vitro of glioperazine C and its derivatives, synthesis and biological evaluation of a post-synthetically trp-based diketopiperazine and it’s antitumor structure-activity relationship. | [Definition]
ChEBI: A pyrrolopyrazine that is hexahydropyrrolo[1,2-a]pyrazine-1,4-dione bearing an indol-3-ylmethyl substituent at position 3 (the 3S,8aS-diastereomer, obtained by formal cyclocondensation of L-tr
ptophan and L-proline). | [IC 50]
PI3Kα: 4.8 μM (IC50) | [References]
[1] XIAO-YONG ZHANG. Antifouling potentials of eight deep-sea-derived fungi from the South China Sea.[J]. Journal of Industrial Microbiology & Biotechnology, 2014, 41 4: 741-748. DOI: 10.1007/s10295-014-1412-9
[2] RAOUDHA BEN AMEUR MEHDI. Five naturally bioactive molecules including two rhamnopyranoside derivatives isolated from the Streptomyces sp. strain TN58.[J]. Natural Product Research, 2009: 1095-1107. DOI: 10.1080/14786410802362352
[3] PEI HUANG. Anti-MRSA and anti-TB metabolites from marine-derived Verrucosispora sp. MS100047[J]. Applied Microbiology and Biotechnology, 2016, 100 17: 7437-7447. DOI: 10.1007/s00253-016-7406-y |
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