APG-1387

Synopsis, Chemistry

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Also known as: Apg-1387, 1570231-89-8, E53vn70k2x, Apg1387, (s,5s,5's,8s,8's,10ar,10a'r)-3,3'-(1,3-phenylenedisulfonyl)bis(n-benzhydryl-5-((s)-2-(methylamino)propanamido)-6-oxodecahydropyrrolo[1,2-a][1,5]diazocine-8-carboxamide), Unii-e53vn70k2x

Molecular Formula

C₆₀H₇₂N₁₀O₁₀S₂

Molecular Weight

1157.4 g/mol

InChI Key

AKLBERUGKZNEJY-RTEPGWBGSA-N

FDA UNII

E53VN70K2X

IAP Inhibitor APG-1387 is a small molecule, second mitochondria-derived activator of caspases (SMAC)-mimetic targeting inhibitor of apoptosis proteins (IAPs) with potential apoptosis-inducing and antineoplastic activities. Upon administration, IAP inhibitor APG-1387 selectively binds to and inhibits the activity of IAPs including X chromosome-linked IAP (XIAP) and cellular IAPs 1 (c-IAP1) and 2 (c-IAP2). This may restore and promote the induction of apoptosis through apoptotic signaling pathways and enhance proteasomal degradation of IAPs. Additionally, APG-1387 may work synergistically with cytotoxic drugs to overcome tumor cell resistance to apoptosis. IAPs are overexpressed by many cancer cell types, suppressing apoptosis by binding and inhibiting active caspases-3, -7 and -9 via their BIR (baculoviral lAP repeat) domains.

1 2D Structure

APG-1387

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(5S,8S,10aR)-3-[3-[[(5S,8S,10aR)-8-(benzhydrylcarbamoyl)-5-[[(2S)-2-(methylamino)propanoyl]amino]-6-oxo-1,2,4,5,8,9,10,10a-octahydropyrrolo[1,2-a][1,5]diazocin-3-yl]sulfonyl]phenyl]sulfonyl-N-benzhydryl-5-[[(2S)-2-(methylamino)propanoyl]amino]-6-oxo-1,2,4,5,8,9,10,10a-octahydropyrrolo[1,2-a][1,5]diazocine-8-carboxamide

2.1.2 InChI

InChI=1S/C60H72N10O10S2/c1-39(61-3)55(71)63-49-37-67(34-32-45-28-30-51(69(45)59(49)75)57(73)65-53(41-18-9-5-10-19-41)42-20-11-6-12-21-42)81(77,78)47-26-17-27-48(36-47)82(79,80)68-35-33-46-29-31-52(70(46)60(76)50(38-68)64-56(72)40(2)62-4)58(74)66-54(43-22-13-7-14-23-43)44-24-15-8-16-25-44/h5-27,36,39-40,45-46,49-54,61-62H,28-35,37-38H2,1-4H3,(H,63,71)(H,64,72)(H,65,73)(H,66,74)/t39-,40-,45+,46+,49-,50-,51-,52-/m0/s1

2.1.3 InChI Key

AKLBERUGKZNEJY-RTEPGWBGSA-N

2.1.4 Canonical SMILES

CC(C(=O)NC1CN(CCC2CCC(N2C1=O)C(=O)NC(C3=CC=CC=C3)C4=CC=CC=C4)S(=O)(=O)C5=CC(=CC=C5)S(=O)(=O)N6CCC7CCC(N7C(=O)C(C6)NC(=O)C(C)NC)C(=O)NC(C8=CC=CC=C8)C9=CC=CC=C9)NC

2.1.5 Isomeric SMILES

C[C@@H](C(=O)N[C@H]1CN(CC[C@H]2CC[C@H](N2C1=O)C(=O)NC(C3=CC=CC=C3)C4=CC=CC=C4)S(=O)(=O)C5=CC(=CC=C5)S(=O)(=O)N6CC[C@H]7CC[C@H](N7C(=O)[C@H](C6)NC(=O)[C@H](C)NC)C(=O)NC(C8=CC=CC=C8)C9=CC=CC=C9)NC

2.2 Other Identifiers

2.2.1 UNII

E53VN70K2X

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Apg-1387

2.3.2 Depositor-Supplied Synonyms

1. Apg-1387

2. 1570231-89-8

3. E53vn70k2x

4. Apg1387

5. (s,5s,5's,8s,8's,10ar,10a'r)-3,3'-(1,3-phenylenedisulfonyl)bis(n-benzhydryl-5-((s)-2-(methylamino)propanamido)-6-oxodecahydropyrrolo[1,2-a][1,5]diazocine-8-carboxamide)

6. Unii-e53vn70k2x

7. Schembl15490706

8. Apg-1387 [who-dd]

9. A][1,5]diazocine-8-carboxamide)

10. Ex-a5180

11. Apg-1387 (smac Mimetic)

12. Nsc834197

13. Nsc-834197

14. Sm-1387

15. Hy-125593

16. Cs-0092417

17. Phenylenedisulfonyl)bis(n-benzhydryl-5-((s)-2-

18. (methylamino)propanamido)-6-oxodecahydropyrrolo[1,2-

19. (5s,5's,8s,8's,10ar,10a'r)-3,3'-(1,3-

2.4 Create Date

2014-03-31

3 Chemical and Physical Properties

Molecular Formula	C₆₀H₇₂N₁₀O₁₀S₂
Molecular Weight	1157.4 g/mol
XLogP3	4.5
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	14
Rotatable Bond Count	18
Exact Mass	1156.48743088 g/mol
Monoisotopic Mass	1156.48743088 g/mol
Topological Polar Surface Area	273 Å²
Heavy Atom Count	82
Formal Charge	0
Complexity	2240
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1