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N-[(R)-3-Hydroxycarbamoyl-2-pentylpropanoyl]-L-tert-leucine methyl ester

ID: ALA458586

PubChem CID: 44567568

Max Phase: Preclinical

Molecular Formula: C16H30N2O5

Molecular Weight: 330.43

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  CCCCC[C@H](CC(=O)NO)C(=O)N[C@H](C(=O)OC)C(C)(C)C

Standard InChI:  InChI=1S/C16H30N2O5/c1-6-7-8-9-11(10-12(19)18-22)14(20)17-13(15(21)23-5)16(2,3)4/h11,13,22H,6-10H2,1-5H3,(H,17,20)(H,18,19)/t11-,13-/m1/s1

Standard InChI Key:  SSLGWMMLEYMVQE-DGCLKSJQSA-N

Molfile:  

     RDKit          2D

 23 22  0  0  0  0  0  0  0  0999 V2000
   11.1875  -26.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9020  -25.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4730  -25.7458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1875  -26.9833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7586  -26.1583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6164  -26.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3309  -25.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6164  -26.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0454  -26.1583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3309  -24.9208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7599  -25.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4743  -26.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7599  -24.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4743  -26.9833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1888  -25.7458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9033  -26.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3309  -27.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3309  -28.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0454  -28.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0454  -29.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7542  -24.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5848  -24.9180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9349  -24.9279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
  1  2  1  0
 11 13  1  1
  6  7  1  0
 12 14  2  0
  1  4  2  0
 12 15  1  0
  6  8  1  6
 15 16  1  0
  8 17  1  0
  7  9  1  0
 17 18  1  0
  3  5  1  0
 18 19  1  0
  7 10  2  0
 19 20  1  0
  1  3  1  0
 13 21  1  0
  9 11  1  0
 13 22  1  0
  2  6  1  0
 13 23  1  0
M  END

Associated Targets(Human)

BIRC2 Tchem Baculoviral IAP repeat-containing protein 2 (984 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Calculated Properties

Molecular Weight: 330.43Molecular Weight (Monoisotopic): 330.2155AlogP: 1.78#Rotatable Bonds: 9
Polar Surface Area: 104.73Molecular Species: NEUTRALHBA: 5HBD: 3
#RO5 Violations: HBA (Lipinski): 7HBD (Lipinski): 3#RO5 Violations (Lipinski):
CX Acidic pKa: 8.90CX Basic pKa: CX LogP: 1.99CX LogD: 1.97
Aromatic Rings: Heavy Atoms: 23QED Weighted: 0.26Np Likeness Score: 0.68

References

1. Sato S, Tetsuhashi M, Sekine K, Miyachi H, Naito M, Hashimoto Y, Aoyama H..  (2008)  Degradation-promoters of cellular inhibitor of apoptosis protein 1 based on bestatin and actinonin.,  16  (8): [PMID:18313309] [10.1016/j.bmc.2008.02.024]
2. Zhang, Bin and 8 more authors.  2008-12-11  Design, synthesis, and evaluation of tricyclic, conformationally constrained small-molecule mimetics of second mitochondria-derived activator of caspases.  [PMID:19012392]
3. Sun, Wei and 9 more authors.  2009-02-12  Design, synthesis, and evaluation of potent, nonpeptidic mimetics of second mitochondria-derived activator of caspases.  [PMID:19138149]
4. Cohen, Frederick F and 12 more authors.  2009-03-26  Orally bioavailable antagonists of inhibitor of apoptosis proteins based on an azabicyclooctane scaffold.  [PMID:19228017]
5. Sun, Haiying and 6 more authors.  2010-05-15  Cyclopeptide Smac mimetics as antagonists of IAP proteins.  [PMID:20443226]
6. Cai, Qian and 17 more authors.  2011-04-28  A potent and orally active antagonist (SM-406/AT-406) of multiple inhibitor of apoptosis proteins (IAPs) in clinical development for cancer treatment.  [PMID:21443232]
7. Sun, Haiying and 11 more authors.  2011-05-12  Potent bivalent Smac mimetics: effect of the linker on binding to inhibitor of apoptosis proteins (IAPs) and anticancer activity.  [PMID:21462933]
8. Flygare, John A JA and 41 more authors.  2012-05-10  Discovery of a potent small-molecule antagonist of inhibitor of apoptosis (IAP) proteins and clinical candidate for the treatment of cancer (GDC-0152).  [PMID:22413863]
9. Allensworth, Jennifer L JL, Sauer, Scott J SJ, Lyerly, H Kim HK, Morse, Michael A MA and Devi, Gayathri R GR.  2013-01  Smac mimetic Birinapant induces apoptosis and enhances TRAIL potency in inflammatory breast cancer cells in an IAP-dependent and TNF-α-independent mechanism.  [PMID:23225169]
10. Sheng, Rong R and 13 more authors.  2013-05-23  A potent bivalent Smac mimetic (SM-1200) achieving rapid, complete, and durable tumor regression in mice.  [PMID:23651223]
11. Donnell, Andrew F AF and 28 more authors.  2013-10-24  Benzazepinones and benzoxazepinones as antagonists of inhibitor of apoptosis proteins (IAPs) selective for the second baculovirus IAP repeat (BIR2) domain.  [PMID:24083782]
12. Kester, Robert F RF and 31 more authors.  2013-10-24  Optimization of benzodiazepinones as selective inhibitors of the X-linked inhibitor of apoptosis protein (XIAP) second baculovirus IAP repeat (BIR2) domain.  [PMID:24093940]
13. Perez, Heidi L HL and 14 more authors.  2015-02-12  Discovery of potent heterodimeric antagonists of inhibitor of apoptosis proteins (IAPs) with sustained antitumor activity.  [PMID:25584393]
14. Tamanini, Emiliano E and 18 more authors.  2017-06-08  Discovery of a Potent Nonpeptidomimetic, Small-Molecule Antagonist of Cellular Inhibitor of Apoptosis Protein 1 (cIAP1) and X-Linked Inhibitor of Apoptosis Protein (XIAP).  [PMID:28492317]
15. Baggio, Carlo C and 8 more authors.  2018-07-26  Design of Potent pan-IAP and Lys-Covalent XIAP Selective Inhibitors Using a Thermodynamics Driven Approach.  [PMID:29940121]

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