Basic information
- CAS
61966-08-3- Standard SMILES
CN1N=C(N)c2cn([C@@H]3O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]3O)c3ncnc1c23- InChIKey
URLYINUFLXOMHP-HTVVRFAVSA-N- Molecular formula
- C13H17N6O7P
- Average molar mass
- 400.28 g/mol
- Monoisotopic mass
- 400.0896339
Overview
Triciribine Phosphate is the phosphate salt of the synthetic, cell-permeable tricyclic nucleoside triciribine with potential antineoplastic activity. Triciribine inhibits the phosphorylation, activation, and signalling of Akt-1, -2, and -3, which may result in the inhibition of Akt-expressing tumor cell proliferation. Akts are anti-apoptotic serine/threonine-specific protein kinases that phosphorylate and inactivate components of the apoptotic machinery, including Bcl-xL/Bcl-2-associated death promoter (BAD) and caspase 9.
Names & identifiers
- Preferred name
- Triciribine Phosphate
- IUPAC
- [(2R,3S,4R,5R)-5-(5-amino-7-methyl-2,6,7,9,11-pentazatricyclo[6.3.1.04,12]dodeca-1(12),3,5,8,10-pentaen-2-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
- English name
- Triciribine
- Molecular formula
- C13H17N6O7P
- Molecular weight
- 400.286
Names & synonyms
TRICIRIBINE PHOSPHATE61966-08-3TCN-PNSC-280594Pentaazaacenaphthylene-5' phosphate esterNSC 2805945L5GE3DV88DTXSID30210993NSC2805943-Amino-1,5-dihydro-5-methyl-1-beta-D-ribofuranosyl-1,4,5,6,8-pentaazaacenaphthylene 5'-(dihydrogen phosphate)TCN-monophosphate1,4,5,6,8-Pentaazaacenaphthylen-3-amine, 1,5-dihydro-5-methyl-1-(5-O-phosphono-beta-D-ribofuranosyl)-
Show more names
Triciribine 5'-phosphatePTX200VQD 002PTX 200PTX-200VQD-002 (TCN-P)Sclareol Impurity 1
TCNPTricycloside PhosphateRefChem:203200DTXCID60133484Tricyclic Nucleoside 5'-Phosphate1,4,5,6,8-pentaazaacenaphthylene-3-amino-1,5-dihydro-5-methyl-1-beta-D-ribofuranosyl 5'-phosphate ester(((2R,3S,4R,5R)-5-(5-amino-7-methyl-2,6,7,9,11-pentaazatricyclo(6.3.1.0^(4,12))dodeca-1(12),3,5,8,10-pentaen-2-yl)-3,4-dihydroxyoxolan-2-yl)methoxy)phosphonic acid1, 5-Dihydro-5-methyl-1-(5-O-phosphono-beta-D-ribofuranosyl)-1,4,5, 6,8-pentaazaacenaphthylen-3-amine
Properties
Computed structural properties
- XLogP
- -3.3
- Topological polar surface area
- 189 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 11
- Rotatable bonds
- 4
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 663
Experimental & physicochemical properties
Solubility
McOH < 1 (mg/mL)
DMSO 1 - 5 (mg/mL)
DMF < 1 (mg/mL)
Trifluoroacetic acid > 50 (mg/mL)
H2O < 1 (mg/mL)
pH 4 Acetate buffer < 1 (mg/mL)
Stability/Shelf LifeBulk: A sample stored at 60 °C for 30 days showed no decomposition (TLC or UV).
Solution: A solution (.0156 mg/mL) in pH 9 carbonate - bicarbonate buffer showed no decomposition after 9 days (UV).
Physicochemical properties
- Density
- 2.23 · 2.23
- solubility
- PBS (pH 7.2): 10 mg/ml
- form
- Solid
- color
- Light yellow to yellow
- FDA UNII
- 5 L5GE3DV88 · 5L5GE3DV88
- NCI Drug Dictionary
- triciribine phosphate
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Toxicity Data
Mouse(ip): LD50: 193 mg/kg
Mouse(iv): LD50: 109 mg/kg
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
UsesTriciribine phosphate is an Akt activation inhibitor that inhibits Akt phosphorylation by binding to the pleckstrin homology (PH) domain of the Akt and blocking its recruitment to the plasma membrane.
Suppliers24 total
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]
欧利希（湖北）医药科技有限公司17316404525 17316404525 · [email protected]
China Kouting Group Limited+86 (21) 5811-6473 5811-6475 · [email protected]
上海梅凯科技有限公司021-68689288 15300790979 · [email protected]
济南精合医药科技有限公司0531-88811783 · [email protected]
玺标（上海）科技有限公司18512111473 18512111473 · [email protected]
AdooQ BioScience, LLC+1 (866) 930-6790 · [email protected]
Wuhan NCE Biomedical Co.,Ltd.4000-027-021 |24 +86-13986109188 | +86-15623472865 | +81-08033611988
上海偕腾生物科技有限公司+86-021-58975553 · [email protected]
Related reactions
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No reaction records under the current filter.
Compound notes
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