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ACTIVE PHARMA INGREDIENTS

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Also known as: 123884-00-4, Dolostatin 15, J9zks885h5, Nsc 617668, (s)-1-((s)-2-benzyl-3-methoxy-5-oxo-2,5-dihydro-1h-pyrrol-1-yl)-3-methyl-1-oxobutan-2-yl n-dimethyl-l-valyl-l-valyl-n-methyl-l-valyl-l-prolyl-l-prolinate, L-proline, n,n-dimethyl-l-valyl-l-valyl-n-methyl-l-valyl-l-prolyl-, (1s)-1-[[(2s)-2,5-dihydro-3-methoxy-5-oxo-2-(phenylmethyl)-1h-pyrrol-1-yl]carbonyl]-2-methylpropyl ester

Molecular Formula

C₄₅H₆₈N₆O₉

Molecular Weight

837.1 g/mol

InChI Key

LQKSHSFQQRCAFW-CCVNJFHASA-N

FDA UNII

J9ZKS885H5

Dolastatin 15 is a depsipeptide originally isolated from the marine mollusk Dolabella auricularia with potential antineoplastic activity. Less potent than the structurally-related compound dolastatin 10, dolastatin 15 binds weakly to tubulin and blocks microtubule assembly, thereby inhibiting mitosis. Dolastatin 15 also induces tumor cell apoptosis through a mechanism involving bcl-2, an oncoprotein that is overexpressed in some cancers. (NCI04)

1 2D Structure

Dolastatin 15

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(2S)-1-[(2S)-2-benzyl-3-methoxy-5-oxo-2H-pyrrol-1-yl]-3-methyl-1-oxobutan-2-yl] (2S)-1-[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-(dimethylamino)-3-methylbutanoyl]amino]-3-methylbutanoyl]-methylamino]-3-methylbutanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carboxylate

2.1.2 InChI

InChI=1S/C45H68N6O9/c1-26(2)36(46-40(53)37(27(3)4)47(9)10)42(55)48(11)38(28(5)6)43(56)49-22-16-20-31(49)41(54)50-23-17-21-32(50)45(58)60-39(29(7)8)44(57)51-33(34(59-12)25-35(51)52)24-30-18-14-13-15-19-30/h13-15,18-19,25-29,31-33,36-39H,16-17,20-24H2,1-12H3,(H,46,53)/t31-,32-,33-,36-,37-,38-,39-/m0/s1

2.1.3 InChI Key

LQKSHSFQQRCAFW-CCVNJFHASA-N

2.1.4 Canonical SMILES

CC(C)C(C(=O)N(C)C(C(C)C)C(=O)N1CCCC1C(=O)N2CCCC2C(=O)OC(C(C)C)C(=O)N3C(C(=CC3=O)OC)CC4=CC=CC=C4)NC(=O)C(C(C)C)N(C)C

2.1.5 Isomeric SMILES

CC(C)[C@@H](C(=O)N(C)[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)N2CCC[C@H]2C(=O)O[C@@H](C(C)C)C(=O)N3[C@H](C(=CC3=O)OC)CC4=CC=CC=C4)NC(=O)[C@H](C(C)C)N(C)C

2.2 Other Identifiers

2.2.1 UNII

J9ZKS885H5

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Nsc 617668

2.3.2 Depositor-Supplied Synonyms

1. 123884-00-4

2. Dolostatin 15

3. J9zks885h5

4. Nsc 617668

5. (s)-1-((s)-2-benzyl-3-methoxy-5-oxo-2,5-dihydro-1h-pyrrol-1-yl)-3-methyl-1-oxobutan-2-yl N-dimethyl-l-valyl-l-valyl-n-methyl-l-valyl-l-prolyl-l-prolinate

6. L-proline, N,n-dimethyl-l-valyl-l-valyl-n-methyl-l-valyl-l-prolyl-, (1s)-1-[[(2s)-2,5-dihydro-3-methoxy-5-oxo-2-(phenylmethyl)-1h-pyrrol-1-yl]carbonyl]-2-methylpropyl Ester

7. Nsc-617668

8. L-proline, N,n-dimethyl-l-valyl-l-valyl-n-methyl-l-valyl-l-prolyl-, (1s)-1-(((2s)-2,5-dihydro-3-methoxy-5-oxo-2-(phenylmethyl)-1h-pyrrol-1-yl)carbonyl)-2-methylpropyl Ester

9. Mfcd00236968

10. Unii-j9zks885h5

11. Dolastatin 15, >=95%

12. Chembl35769

13. Schembl187502

14. Dls-15

15. Dtxsid30924629

16. Hy-p1126

17. Bdbm50472220

18. Zinc95611960

19. Cs-0027988

20. J-004993

21. [(2s)-1-[(2s)-2-benzyl-3-methoxy-5-oxo-2h-pyrrol-1-yl]-3-methyl-1-oxobutan-2-yl] (2s)-1-[(2s)-1-[(2s)-2-[[(2s)-2-[[(2s)-2-(dimethylamino)-3-methylbutanoyl]amino]-3-methylbutanoyl]-methylamino]-3-methylbutanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carboxylate

22. L-proline, 1-(1-(n-(n-(n,n-dimethyl-l-valyl)-l-valyl)-n-methyl-l-valyl)-l-prolyl)-, 1-((2,5-dihydro-3-methoxy-5-oxo-2-(phenylmethyl)-1h-pyrrol-1-yl)carbonyl)-2-methylpropyl Ester, (s-(r*,r*))-

23. L-proline, 1-(1-(n-(n-(n,n-dimethyl-l-valyl)-l-valyl)-n-methyl-l-valyl)-l-propyl)-, 1-((2,5-dihydro-3-methoxy-5-oxo-2-(phenylmethyl)-1h-pyrrol-1-yl)carbonyl)-2-methylpropyl Ester, (s-(r*,r*))-

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₄₅H₆₈N₆O₉
Molecular Weight	837.1 g/mol
XLogP3	5.7
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	18
Exact Mass	836.50477777 g/mol
Monoisotopic Mass	836.50477777 g/mol
Topological Polar Surface Area	166 Å²
Heavy Atom Count	60
Formal Charge	0
Complexity	1600
Isotope Atom Count	0
Defined Atom Stereocenter Count	7
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1