6,9-Dibenzyl-1,4,7-trihydroxy-3-[6-(oxiran-2-yl)-6-oxohexyl]-3,6,9,12,13,14,15,15a-octahydro-10H-pyrido[1,2-a][1,4,7,10]tetraazacyclododecin-10-one
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Grundinformationen
- CAS
133155-89-2- Standard-SMILES
O=C1N[C@@H](Cc2ccccc2)C(=O)N2CCCC[C@@H]2C(=O)N[C@@H](CCCCCC(=O)[C@@H]2CO2)C(=O)N[C@H]1Cc1ccccc1- InChIKey
GXVXXETYXSPSOA-UFEOFEBPSA-N- Summenformel
- C34H42N4O6
- Durchschnittliche Molmasse
- 602,732 g/mol
- Monoisotopische Masse
- 602,31043506
Namen und Bezeichner
- Bevorzugter Name
- 6,9-Dibenzyl-1,4,7-trihydroxy-3-[6-(oxiran-2-yl)-6-oxohexyl]-3,6,9,12,13,14,15,15a-octahydro-10H-pyrido[1,2-a][1,4,7,10]tetraazacyclododecin-10-one
- IUPAC
- (3S,6S,9S,15aR)-6,9-Dibenzyl-1,4,7-trihydroxy-3-{6-[(2S)-oxiran-2-yl]-6-oxohexyl}-3,6,9,12,13,14,15,15a-octahydro-10H-pyrido[1,2-a][1,4,7,10]tetraazacyclododecin-10-one
- Englischer Name
- trapoxin A
- Summenformel
- C34H42N4O6
- Molmasse
- 602.72
Namen und Synonyme
RF-1023Atrapoxin ACyclo[L-Phe-L-Phe-D-Hpr-6-[2-[(S)-oxiranyl]-2-oxoethyl]-L-Nle-]Cyclo((S)-phenylalanyl-(S)-phenylalanyl-(R)-pipecolinyl-(2S,9S)-2-amino-8-oxo-9,10-epoxydecanoyl)Cyclo[(αS,2S)-α-amino-η-oxo-2-oxiraneoctanoyl-L-phenylalanyl-L-phenylalanyl-(2R)-2-piperidinecarbonyl]Cyclo[(aS,2S)-a-amino-h-oxo-2-oxiraneoctanoyl-L-phenylalanyl-L-phenylalanyl-(2R)-2-piperidinecarbonyl](4aR,7S,10S,13S)-10,13-Dibenzyl-7-[6-oxo-6-[(S)-oxiranyl]hexyl]-1,2,3,4,9,10-hexahydro-4aH-6,9,12,14a-tetraazabenzocyclododecene-5,8,11,14(6H,7H,12H,13H)-tetrone
Datenbank-Bezeichner
- CAS
133155-89-2- PubChem CID
- 121875
- DTXSID
DTXSID20927982- ChEMBL
CHEMBL274445、CHEMBL6087370- ChEBI
CHEBI:84057- UNII
- GSS8DX555X
- EC Number
- 687-014-6
- Nikkaji
- J359.332K
Eigenschaften
Physikochemische Eigenschaften
- Siedepunkt
- 928.258 · 928.258±65.00 °C(Press: 760.00 Torr)(predicted)
- Dichte
- 1.276 · 1.276±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- storage temp.
- -20 °C · -20°C
- Löslichkeit
- 0.9 · DMSO: soluble0.9-1.10 mg/ml, clear, colorless to faintly yellow (may be further diluted 20 fold in H2O)
- Aggregatzustand
- solid
- pka
- 13.316 · 13.316±0.70(predicted)
- Biologische Quelle
- Helicoma ambiens
- InChIKey
- GXVXXETYXSPSOA-UFEOFEBPSA-N
- SMILES
- N21[C@H](CCCC2)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C1=O)Cc5ccccc5)Cc4ccccc4)CCCCCC(=O)[C@H]3OC3
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- wgk
- 3
- ridadr
- UN 2811 6.1 / PGIII
- risk_code
- 25
- hazard_code
- T
- safety_code
- 45
- Speicherklasse
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- Acute Tox. 3 Oral
Chemie und Industrie
Anwendungen
BeschreibungTrapoxin A is a cyclotetrapeptide histone deacetylase (HDAC) inhibitor. It inhibits HDAC activity in a concentration-dependent and irreversible manner. Trapoxin A inhibits proliferation of NIH3T3 cells transformed by the oncogene v-sis (sis/NIH3T3; IC50 = ~200 ng/ml) and has detransformation activity, flattening sis/NIH3T3 cells when used at a concentration of 1 ng/ml. It also halts the cell cycle at the G2 phase in 3Y1 fibroblasts when used at a concentration of 10 nM and inhibits growth of TR303 cells resistant to trichostatin A at a concentration of 50 ng/ml.
VerwendenTrapoxin A has been used:to study its effects on the inhibition of histone deacetylase 11 (HDAC11)to study its effects on the inhibition of HDAC3 in human cell linesto study its effects on the inhibition of HDAC6 in rat pyramidal neurons
Anbieter4 Anbieter
InvivoChem中国13549236410 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
BOC Sciences16314854226 · [email protected]
ChemeGen 中国18818260767 · [email protected]
Ergänzende Hinweise
DefinitionChEBI: A homodetic cyclic tetrapeptide constructed from L-phenylalanyl (x2), D-pipecolinyl and L-2-amino-8-oxo-9,10-epoxydecanoyl residues.
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