ID: ALA374308

Max Phase: Preclinical

Molecular Formula: C15H24N2O7S

Molecular Weight: 376.43

Molecule Type: Small molecule

Representations

Synonyms (1): Lactacystin
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC(=O)N[C@@H](CSC(=O)[C@]1([C@@H](O)C(C)C)NC(=O)[C@H](C)[C@@H]1O)C(=O)O

Standard InChI:  InChI=1S/C15H24N2O7S/c1-6(2)10(19)15(11(20)7(3)12(21)17-15)14(24)25-5-9(13(22)23)16-8(4)18/h6-7,9-11,19-20H,5H2,1-4H3,(H,16,18)(H,17,21)(H,22,23)/t7-,9+,10+,11+,15-/m1/s1

Standard InChI Key:  DAQAKHDKYAWHCG-RWTHQLGUSA-N

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

Properties

Molecular Weight: 376.43

Molecular Weight (Monoisotopic): 376.1304

AlogP: -1.28

#Rotatable Bonds: 7

Polar Surface Area: 153.03

Molecular Species: ACID

HBA: 7

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 3.64

CX Basic pKa:

CX LogP: -1.22

CX LogD: -4.55

Aromatic Rings: 0

Heavy Atoms: 25

QED Weighted: 0.37

Np Likeness Score: 1.19

References

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6. PubChem BioAssay data set, 

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8. Qian K, Kim SY, Hung HY, Huang L, Chen CH, Lee KH..  (2011)  New betulinic acid derivatives as potent proteasome inhibitors.,  21  (19): [PMID:21856154] [10.1016/j.bmcl.2011.07.072]

9. Xu D, Ondeyka J, Harris GH, Zink D, Kahn JN, Wang H, Bills G, Platas G, Wang W, Szewczak AA, Liberator P, Roemer T, Singh SB..  (2011)  Isolation, structure, and biological activities of Fellutamides C and D from an undescribed Metulocladosporiella (Chaetothyriales) using the genome-wide Candida albicans fitness test.,  74  (8): [PMID:21761939] [10.1021/np2001573]

10. Beck J, Guminski Y, Long C, Marcourt L, Derguini F, Plisson F, Grondin A, Vandenberghe I, Vispé S, Brel V, Aussagues Y, Ausseil F, Arimondo PB, Massiot G, Sautel F, Cantagrel F..  (2012)  Semisynthetic neoboutomellerone derivatives as ubiquitin-proteasome pathway inhibitors.,  20  (2): [PMID:22206869] [10.1016/j.bmc.2011.11.066]

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12. Liu Y, Qian K, Wang CY, Chen CH, Yang X, Lee KH..  (2012)  Synthesis and biological evaluation of novel spin labeled 18β-glycyrrhetinic acid derivatives.,  22  (24): [PMID:23122524] [10.1016/j.bmcl.2012.10.041]

13. Kawamura S, Unno Y, List A, Mizuno A, Tanaka M, Sasaki T, Arisawa M, Asai A, Groll M, Shuto S..  (2013)  Potent proteasome inhibitors derived from the unnatural cis-cyclopropane isomer of Belactosin A: synthesis, biological activity, and mode of action.,  56  (9): [PMID:23547757] [10.1021/jm4002296]

14. Ozcan S, Kazi A, Marsilio F, Fang B, Guida WC, Koomen J, Lawrence HR, Sebti SM..  (2013)  Oxadiazole-isopropylamides as potent and noncovalent proteasome inhibitors.,  56  (10): [PMID:23547706] [10.1021/jm400221d]

15. Kawamura S, Unno Y, Asai A, Arisawa M, Shuto S..  (2014)  Structurally novel highly potent proteasome inhibitors created by the structure-based hybridization of nonpeptidic belactosin derivatives and peptide boronates.,  57  (6): [PMID:24524217] [10.1021/jm500045x]

16. Xu K, Wang K, Yang Y, Yan DA, Huang L, Chen CH, Xiao Z..  (2015)  Discovery of novel non-covalent inhibitors selective to the β5-subunit of the human 20S proteasome.,  98  [PMID:26005024] [10.1016/j.ejmech.2015.05.023]

17. Tanaka M, Zhu Y, Shionyu M, Ota N, Shibata N, Watanabe C, Mizusawa A, Sasaki R, Mizukami T, Shiina I, Hasegawa M..  (2018)  Ridaifen-F conjugated with cell-penetrating peptides inhibits intracellular proteasome activities and induces drug-resistant cell death.,  146  [PMID:29407987] [10.1016/j.ejmech.2018.01.045]

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Source

Source(2):

• Scientific Literature
• PubChem BioAssays