Basic information
- CAS
38136-70-8- Standard SMILES
O=C1N[C@@H](Cc2c[nH]c3ccccc23)C(=O)N2CCC[C@@H]12- InChIKey
RYFZBPVMVYTEKZ-KBPBESRZSA-N- Molecular formula
- C16H17N3O2
- Average molar mass
- 283.32 g/mol
- Monoisotopic mass
- 283.13207679
Overview
Brevianamide F is 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-tryptophan and L-proline). It has a role as a metabolite. It is a member of indoles, a dipeptide and a pyrrolopyrazine.
Names & identifiers
- Preferred name
- Brevianamide F
- IUPAC
- (3S,8aS)-3-(1H-indol-3-ylmethyl)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
- English name
- Cyclo(L-Pro-L-Trp-)
- Molecular formula
- C16H17N3O2
- Molecular weight
- 283.33
Names & synonyms
Brevianamide F38136-70-8L-prolyl-L-tryptophan anhydrideCyclo-L-Trp-L-Pro76XZ426FPP(3s,8as)-3-(1h-Indol-3-Ylmethyl)hexahydropyrrolo[1,2-A]pyrazine-1,4-DioneCHEBI:64530DTXSID10959075(3S,8aS)-3-(1H-indol-3-ylmethyl)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione(3S,8aS)-3-(1H-indol-3-ylmethyl)hexahydropyrrolo(1,2-a)pyrazine-1,4-dione(3S,8aS)-3-(1H-indol-3-ylmethyl)-2,3,6,7,8,8a-hexahydropyrrolo(1,2-a)pyrazine-1,4-dioneRefChem:121343
Show more names
Trp-Pro-diketopiperazine Eptifibatidec(Trp-Pro)Cyclo(-Trp-Pro)Cyclo(L-Trp-L-Pro-)Cyclo(L-Pro-L-Trp-)Eptifibatide Impurity 11Cyclo-L-tryptophyl-L-prolineBrevianamide F, 10 mM in DMSO
DTXCID101386965cyclo-(Trp-Pro)(3S,8aS)-3-((1H-Indol-3-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dioneMFCD29917326L-tryptophyl-L-proline cyclic anhydridecyclo-L-proline-L-pryptophancyclo-L-tryptophanyl-L-prolinetryptophan-proline diketopiperazine
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 65.2 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 453
Physicochemical properties
- Melting point
- 165 · 165-167 °C
- Boiling point
- 633.2 · 633.2±48.0 °C(Predicted)
- Density
- 1.37 · 1.37±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 13.2 · 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
- FDA UNII
- 76 XZ426FPP · 76XZ426FPP
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
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
- wgk
- WGK 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P264-P280-P302+P352-P321-P332+P313-P362-P305+P351+P338-P337+P313-P261-P271-P304+P340-P312-P403+P233-P405-P501
Chemistry & industry
Applications
DescriptionBrevianamide F is an alkaloid metabolite produced by various Streptomyces, Actinomycetes, and Aspergillus strains that has diverse biological activities. 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). 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).
UsesBrevianamide 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.
Suppliers73 total
陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
武汉众志诚生物技术有限公司13628624121 13628604890 · [email protected]
上海弘顺生物科技有限公司15901914505 · [email protected]
南通先行生物医药科技有限公司513-85982855 18921614129 · [email protected]
安耐吉化学&3A（安徽泽升科技有限公司）021-58432009 400-005-6266 · [email protected]
孟成科技（上海）有限公司
Related reactions
0 records
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Compound notes
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