Tryprostatin A
Basic information
- CAS
171864-80-5- Standard SMILES
COc1ccc2c(C[C@@H]3NC(=O)[C@@H]4CCCN4C3=O)c(CC=C(C)C)[nH]c2c1- InChIKey
XNRPVPHNDQHWLJ-PMACEKPBSA-N- Molecular formula
- C22H27N3O3
- Average molar mass
- 381.5 g/mol
- Monoisotopic mass
- 381.20524173
Overview
Tryprostatin A is a cyclic dipeptide that is brevianamide F (cyclo-L-Trp-L-Pro) substituted at positions 2 and 6 on the indole ring by prenyl and methoxy groups respectively. It has a role as a breast cancer resistance protein inhibitor. It is a member of indoles, an aromatic ether, an indole alkaloid, a dipeptide and a pyrrolopyrazine. It is functionally related to a brevianamide F.
Names & identifiers
- Preferred name
- Tryprostatin A
- IUPAC
- (3S,8aS)-3-[[6-methoxy-2-(3-methylbut-2-enyl)-1H-indol-3-yl]methyl]-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
- English name
- TRYPROSTATIN A
- Molecular formula
- C22H27N3O3
- Molecular weight
- 381.47
Names & synonyms
Tryprostatin A171864-80-5CHEBI:72761(3S,8aS)-3-[[6-methoxy-2-(3-methylbut-2-enyl)-1H-indol-3-yl]methyl]-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione(3S,8aS)-3-{[6-methoxy-2-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}hexahydropyrrolo[1,2-a]pyrazine-1,4-dioneDTXSID701017629(3S,8aS)-3-((6-Methoxy-2-(3-methylbut-2-en-1-yl)-1H-indol-3-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione(3S,8aS)-3-((6-Methoxy-2-(3-methylbut-2-en-1-yl)-1H-indol-3-yl)methyl)hexahydropyrrolo(1,2-a)pyrazine-1,4-dione(3S,8aS)-3-((6-methoxy-2-(3-methylbut-2-enyl)-1H-indol-3-yl)methyl)-2,3,6,7,8,8a-hexahydropyrrolo(1,2-a)pyrazine-1,4-dioneRefChem:192354DTXCID401475814TryprostatinA
Show more names
TRYPROSTATIN BPyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-[[6-methoxy-2-(3-methyl-2-buten-1-yl)-1H-indol-3-yl]methyl]-, (3S,8aS)-
TPS-ACHEMBL289159MEGxm0_000107orb1681527SCHEMBL21263139SCHEMBL29948084HY-N7291BDBM50198769
Properties
Computed structural properties
- XLogP
- 3.4
- Topological polar surface area
- 74.4 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 5
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 645
Physicochemical properties
- Melting point
- 119 · 119-120 °C
- Boiling point
- 666.4 · 666.4±55.0 °C(Predicted)
- Density
- 1.26 · 1.26±0.1 g/cm3(Predicted)
- pka
- 12.99 · 12.99±0.40(Predicted)
- form
- White powder.
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319
- Precautionary statements
- 264 · P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
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
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H315-H319
- Precautionary statements
- P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
Chemistry & industry
Applications
UsesTryprostatin A is an inhibitor of the mammalian cell cycle. Tryprostatins A can be isolated from the secondary metabolites of a marine fungal strain BM939[1].
Additional notes
DefinitionChEBI: Tryprostatin A is a cyclic dipeptide that is brevianamide F (cyclo-L-Trp-L-Pro) substituted at positions 2 and 6 on the indole ring by prenyl and methoxy groups respectively. It has a role as a breast cancer resistance protein inhibitor. It is a dipeptide, a member of indoles, a pyrrolopyrazine, an aromatic ether and an indole alkaloid. It is functionally related to a brevianamide F.
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