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Chemistry

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Also known as: Tp-1287, 2044686-42-0, 4h-1-benzopyran-4-one, 2-(2-chlorophenyl)-5-hydroxy-8-((3s,4r)-3-hydroxy-1-methyl-4-piperidinyl)-7-(phosphonooxy)-, Alvocidib phosphate, Unii-7mpp85iij3, Alvocidib prodrug tp-1287
Molecular Formula
C21H21ClNO8P
Molecular Weight
481.8  g/mol
InChI Key
YRNFLVUMZIRYKY-BLLLJJGKSA-N
FDA UNII
7MPP85IIJ3

TP-1287
Alvocidib Prodrug TP-1287 is an orally bioavailable, highly soluble phosphate prodrug of alvocidib, a potent inhibitor of cyclin-dependent kinase-9 (CDK9), with potential antineoplastic activity. Upon administration of the phosphate prodrug TP-1287, the prodrug is enzymatically cleaved at the tumor site and the active moiety alvocidib is released. Alvocidib targets and binds to CDK9, thereby reducing the expression of CDK9 target genes such as the anti-apoptotic protein MCL-1, and inducing G1 cell cycle arrest and apoptosis in CDK9-overexpressing cancer cells.
1 2D Structure

TP-1287

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[2-(2-chlorophenyl)-5-hydroxy-8-[(3S,4R)-3-hydroxy-1-methylpiperidin-4-yl]-4-oxochromen-7-yl] dihydrogen phosphate
2.1.2 InChI
InChI=1S/C21H21ClNO8P/c1-23-7-6-12(16(26)10-23)19-18(31-32(27,28)29)9-15(25)20-14(24)8-17(30-21(19)20)11-4-2-3-5-13(11)22/h2-5,8-9,12,16,25-26H,6-7,10H2,1H3,(H2,27,28,29)/t12-,16+/m0/s1
2.1.3 InChI Key
YRNFLVUMZIRYKY-BLLLJJGKSA-N
2.1.4 Canonical SMILES
CN1CCC(C(C1)O)C2=C(C=C(C3=C2OC(=CC3=O)C4=CC=CC=C4Cl)O)OP(=O)(O)O
2.1.5 Isomeric SMILES
CN1CC[C@@H]([C@@H](C1)O)C2=C(C=C(C3=C2OC(=CC3=O)C4=CC=CC=C4Cl)O)OP(=O)(O)O
2.2 Other Identifiers
2.2.1 UNII
7MPP85IIJ3
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. Tp-1287

2. 2044686-42-0

3. 4h-1-benzopyran-4-one, 2-(2-chlorophenyl)-5-hydroxy-8-((3s,4r)-3-hydroxy-1-methyl-4-piperidinyl)-7-(phosphonooxy)-

4. Alvocidib Phosphate

5. Unii-7mpp85iij3

6. Alvocidib Prodrug Tp-1287

7. Chembl4594423

8. Schembl18251861

9. Tp-1287 [who-dd]

10. Bdbm50553482

11. Tp1287

2.4 Create Date
2017-02-18
3 Chemical and Physical Properties
Molecular Weight 481.8 g/mol
Molecular Formula C21H21ClNO8P
XLogP3-0.3
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count9
Rotatable Bond Count4
Exact Mass481.0693313 g/mol
Monoisotopic Mass481.0693313 g/mol
Topological Polar Surface Area137 Ų
Heavy Atom Count32
Formal Charge0
Complexity790
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1

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