(S)-methyl 1-((2R,5S,8S,12S,13S,16S,19S,22S)-16-(3-amino-3-oxopropyl)-2,13-dibenzyl-12,22-dihydroxy-8-isobutyl-19-isopropyl-3,5,17-trimethyl-4,7,10,15,18,21-hexaoxo-3,6,9,14,17,20-hexaazatricosane)pyrrolidine-2-carboxylate

ID: ALA2181015

Chembl Id: CHEMBL2181015

PubChem CID: 70680446

Max Phase: Preclinical

Molecular Formula: C50H74N8O12

Molecular Weight: 979.19

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)[C@H](C)O)C(C)C

Standard InChI:  InChI=1S/C50H74N8O12/c1-29(2)25-36(45(64)52-31(5)47(66)57(8)39(27-34-19-14-11-15-20-34)48(67)58-24-16-21-38(58)50(69)70-9)53-42(62)28-40(60)35(26-33-17-12-10-13-18-33)54-46(65)37(22-23-41(51)61)56(7)49(68)43(30(3)4)55-44(63)32(6)59/h10-15,17-20,29-32,35-40,43,59-60H,16,21-28H2,1-9H3,(H2,51,61)(H,52,64)(H,53,62)(H,54,65)(H,55,63)/t31-,32-,35-,36-,37-,38-,39+,40-,43-/m0/s1

Standard InChI Key:  WFMVRFNXMBGKEW-HVGQEOIXSA-N

Alternative Forms

1. Parent:

   

   ALA2181015

   methyl (2S)-1-[(2R)-2-[[(2S)-2-[[(2S)-2-[[(3S,4S)-4-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-hydroxypropanoyl]amino]-3-methylbutanoyl]-methylamino]-5-oxopentanoyl]amino]-3-hydroxy-5-phenylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]-methylamino]-3-phenyl

Molecule Features

Natural Product: Yes

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: 979.19

Molecular Weight (Monoisotopic): 978.5426

AlogP: 0.35

#Rotatable Bonds: 26

Polar Surface Area: 287.18

Molecular Species: NEUTRAL

HBA: 12

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 20

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.89

CX Basic pKa: ┄

CX LogP: 0.39

CX LogD: 0.39

Aromatic Rings: 2

Heavy Atoms: 70

QED Weighted: 0.06

Np Likeness Score: 0.17

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. Al-Awadhi FH, Ratnayake R, Paul VJ, Luesch H..  (2016)  Tasiamide F, a potent inhibitor of cathepsins D and E from a marine cyanobacterium.,  24  (15): [PMID:27211244] [10.1016/j.bmc.2016.04.062]

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