ChemicalBook--->CAS DataBase List--->847591-62-2

847591-62-2

847591-62-2 Structure

847591-62-2 Structure
IdentificationBack Directory
[Name]

ICG-001
[CAS]

847591-62-2
[Synonyms]

ICG-1
ICG-001
CS-1928
ICG001 isomer
ICG-001 isomer
PRI-724 isomer
ICG-001/ICG001
ICG 001, >=98%
ICG 001 isomer.
ICG-001;ICG 001;ICG001
β-Catenin/Tcf Inhibitor VI, ICG-001 - CAS 847591-62-2 - Calbiochem
(6S,9AS)-6-(4-hydroxybenzyl)-N-benzyl-8-(naphthalen-1-ylmethyl)-4,7-dioxo-hexahydro-2H-pyrazin
(6S,9aS)-Hexahydro-6-[(4-hydroxyphenyl)methyl]-8-(1-naphthalenylmethyl)-4,7-dioxo-N-(phenylmethyl)-2H-pyrazino[1,2-a]pyrimidine-1(6H)-carboxamide
2H-Pyrazino[1,2-a]pyriMidine-1(6H)-carboxaMide, hexahydro-6-[(4-hydroxyphenyl)Methyl]-8-(1-naphthalenylMethyl)-4,7-dioxo-N-(phenylMethyl)-, (6S,9aS)-
(6S,9aS)-Hexahydro-6-[(4-hydroxyphenyl)methyl]-8-(1-naphthalenylmethyl)-4,7-dioxo-N-(phenylmethyl)-2H-pyrazino[1,2-a]pyrimidine-1(6H)-carboxamide ICG001
[Molecular Formula]

C33H32N4O4
[MDL Number]

MFCD12196918
[MOL File]

847591-62-2.mol
[Molecular Weight]

548.632
Chemical PropertiesBack Directory
[density ]

1.37
[storage temp. ]

+2C to +8C
[solubility ]

Soluble in DMSO (up to 50 mg/ml) or in Ethanol (up to 25 mg/ml).
[form ]

Off-white powder
[color ]

Off-white
[Stability:]

Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
[InChIKey]

HQWTUOLCGKIECB-PKGWHCLJNA-N
[SMILES]

C1C(=O)N2[C@@H](Cc3ccc(O)cc3)C(=O)N(Cc3c4ccccc4ccc3)C[C@@H]2N(C(=O)NCc2ccccc2)C1 |&1:4,28,r|
Safety DataBack Directory
[WGK Germany ]

WGK 3
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[Description]

ICG-001 (847591-62-2) inhibits TCF/β-catenin mediated transcription by specifically blocking β-catenin/CBP interaction
[Uses]

(S,S)-ICG 001 is a β-turn peptidomimetic molecule inhibitor of β-catenin-Tcf-mediated transcription.
[Definition]

ChEBI: (6S,9aS)-6-[(4-hydroxyphenyl)methyl]-8-(1-naphthalenylmethyl)-4,7-dioxo-N-(phenylmethyl)-3,6,9,9a-tetrahydro-2H-pyrazino[1,2-a]pyrimidine-1-carboxamide is a peptide.
[General Description]

A cell-permeable pyrazinopyrimidinecarboxamide that competes against β-catenin for CBP (CREB-binding protein) binding and selectively prevents CBP- but not p300-, dependent TCF/β-catenin transcriptional regulations both in cultures in vitro (5 to 25 μM) and in mice in vivo (5 mg/kg/day via osmotic pump infusion), while not affecting CBP-dependent transcriptional activities mediated by the AP-1 or CRE complex. Shown to reactivate p300//TCF/β-catenin-mediated neuronal differentiation upon NGF stimulation in PS-1 L286V mutant-expressing PC-12 cultures and be efficacious in alleviating bleomycin- (0,08 units/50 μL/mouse; administered intranasally; Cat. No. 203401) induced pulmonary fibrosis in mice.
[Biochem/physiol Actions]

Cell permeable: yes
[References]

1) Emami?et al.?(2004),?A small molecule inhibitor of β-catenin/CREB-binding protein transcription;? Proc. Natl. Acad. Sci. USA,?101?12682 2) Zhou?et al.?(2012), Interactions?between β-catenin and transforming growth factor-β signaling pathways mediate epithelial-mesenchymal transition and are dependent on the transcription co-activator cAMP-response element-binding protein (CERB)-binding protein (CBP);??J. Biol. Chem.,?287?7026
Spectrum DetailBack Directory
[Spectrum Detail]

ICG-001(847591-62-2)1HNMR
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