(S)-methyl 1-((5S,8S,11S,12S,16S,19S,22R)-8-(3-amino-3-oxopropyl)-11,22-dibenzyl-12-hydroxy-16-isobutyl-5-isopropyl-7,19,21-trimethyl-3,6,9,14,17,20-hexaoxo-1-phenyl-2-oxa-4,7,10,15,18,21-hexaazatricosane)pyrrolidine-2-carboxylate

ID: ALA2181022

Chembl Id: CHEMBL2181022

PubChem CID: 71453880

Max Phase: Preclinical

Molecular Formula: C55H76N8O12

Molecular Weight: 1041.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@@H]1CCCN1C(=O)[C@@H](Cc1ccccc1)N(C)C(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)C[C@H](O)[C@H](Cc1ccccc1)NC(=O)[C@H](CCC(N)=O)N(C)C(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C

Standard InChI:  InChI=1S/C55H76N8O12/c1-34(2)29-41(49(67)57-36(5)51(69)62(7)44(31-38-21-14-10-15-22-38)52(70)63-28-18-25-43(63)54(72)74-8)58-47(66)32-45(64)40(30-37-19-12-9-13-20-37)59-50(68)42(26-27-46(56)65)61(6)53(71)48(35(3)4)60-55(73)75-33-39-23-16-11-17-24-39/h9-17,19-24,34-36,40-45,48,64H,18,25-33H2,1-8H3,(H2,56,65)(H,57,67)(H,58,66)(H,59,68)(H,60,73)/t36-,40-,41-,42-,43-,44+,45-,48-/m0/s1

Standard InChI Key:  NXDIWJUYMKBICN-QDBLDGTHSA-N

Alternative Forms

1. Parent:

   

   ALA2181022

   methyl (2S)-1-[(2R)-2-[[(2S)-2-[[(2S)-2-[[(3S,4S)-4-[[(2S)-5-amino-2-[methyl-[(2S)-3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]-5-oxopentanoyl]amino]-3-hydroxy-5-phenylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]-methylamino]-3-phenylprop

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 1041.26

Molecular Weight (Monoisotopic): 1040.5583

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References

1. Liu Y, Zhang W, Li L, Salvador LA, Chen T, Chen W, Felsenstein KM, Ladd TB, Price AR, Golde TE, He J, Xu Y, Li Y, Luesch H..  (2012)  Cyanobacterial peptides as a prototype for the design of potent β-secretase inhibitors and the development of selective chemical probes for other aspartic proteases.,  55  (23): [PMID:23181502] [10.1021/jm301630s]

2. Liu J, Chen W, Xu Y, Ren S, Zhang W, Li Y..  (2015)  Design, synthesis and biological evaluation of tasiamide B derivatives as BACE1 inhibitors.,  23  (9): [PMID:25842365] [10.1016/j.bmc.2015.03.034]

3. Li Z, Li H, Jiang F, Wang Z, Zhang W..  (2022)  Cathepsin D inhibitors based on tasiamide B derivatives with cell membrane permeability.,  57  [PMID:35121401] [10.1016/j.bmc.2022.116646]

Source

Source(1):

• Scientific Literature