Thiostrepton 1

ID: ALA2303629

Chembl Id: CHEMBL2303629

PubChem CID: 71720240

Max Phase: Preclinical

Molecular Formula: C72H85N19O18S5

Molecular Weight: 1664.92

Molecule Type: Unknown

Names and Identifiers

Synonyms: Thiostrepton 1 | Thiostrepton 1|thiostrepton|CHEMBL2303629|BDBM50523757

Canonical SMILES:  C=C(NC(=O)C(=C)NC(=O)c1csc(C2=N[C@@H]3c4csc(n4)[C@H]4NC(=O)c5csc(n5)[C@H]([C@@](C)(O)[C@@H](C)O)NC(=O)[C@H]5CSC(=N5)/C(=C/C)NC(=O)[C@H]([C@@H](C)O)NC(=O)c5csc(n5)[C@@]3(CC2)NC(=O)[C@H](C)NC(=O)C(=C)NC(=O)C(C)NC(=O)[C@H]([C@@H](C)CC)N[C@@H]2C=Cc3c([C@H](C)O)cc(nc3[C@H]2O)C(=O)O[C@@H]4C)n1)C(N)=O

Standard InChI:  InChI=1S/C72H85N19O18S5/c1-14-26(3)47-63(105)78-30(7)57(99)75-28(5)56(98)76-31(8)58(100)91-72-19-18-40(66-85-43(22-111-66)59(101)77-29(6)55(97)74-27(4)54(73)96)81-52(72)42-21-112-67(83-42)49(34(11)109-69(107)41-20-37(32(9)92)36-16-17-39(79-47)51(95)50(36)80-41)89-60(102)44-24-113-68(86-44)53(71(13,108)35(12)94)90-62(104)45-23-110-65(84-45)38(15-2)82-64(106)48(33(10)93)88-61(103)46-25-114-70(72)87-46/h15-17,20-22,24-26,30-35,39,45,47-49,51-53,79,92-95,108H,4-6,14,18-19,23H2,1-3,7-13H3,(H2,73,96)(H,74,97)(H,75,99)(H,76,98)(H,77,101)(H,78,105)(H,82,106)(H,88,103)(H,89,102)(H,90,104)(H,91,100)/b38-15-/t26-,30?,31-,32-,33+,34+,35+,39+,45+,47-,48-,49-,51-,52+,53+,71-,72-/m0/s1

Standard InChI Key:  NSFFHOGKXHRQEW-BEEVBQKTSA-N

Alternative Forms

1. Parent:

   

   ALA2303629

   THIOSTREPTON

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 1664.92

Molecular Weight (Monoisotopic): 1663.4924

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References

1. Bower J, Drysdale M, Hebdon R, Jordan A, Lentzen G, Matassova N, Murchie A, Powles J, Roughley S..  (2003)  Structure-based design of agents targeting the bacterial ribosome.,  13  (15): [PMID:12852942] [10.1016/s0960-894x(03)00495-5]

2. Ayida BK, Simonsen KB, Vourloumis D, Hermann T..  (2005)  Synthesis of dehydroalanine fragments as thiostrepton side chain mimetics.,  15  (10): [PMID:15863296] [10.1016/j.bmcl.2005.03.084]

3. Bodoor K, Boyapati V, Gopu V, Boisdore M, Allam K, Miller J, Treleaven WD, Weldeghiorghis T, Aboul-ela F..  (2009)  Design and implementation of an ribonucleic acid (RNA) directed fragment library.,  52  (12): [PMID:19445516] [10.1021/jm9000659]

4. Sidhu AB, Sun Q, Nkrumah LJ, Dunne MW, Sacchettini JC, Fidock DA..  (2007)  In vitro efficacy, resistance selection, and structural modeling studies implicate the malarial parasite apicoplast as the target of azithromycin.,  282  (4): [PMID:17110371] [10.1074/jbc.m608615200]

5. Myers CL, Hang PC, Ng G, Yuen J, Honek JF..  (2010)  Semi-synthetic analogues of thiostrepton delimit the critical nature of tail region modifications in the control of protein biosynthesis and antibacterial activity.,  18  (12): [PMID:20510619] [10.1016/j.bmc.2010.04.098]

6. Ochi K, Kim JY, Tanaka Y, Wang G, Masuda K, Nanamiya H, Okamoto S, Tokuyama S, Adachi Y, Kawamura F..  (2009)  Inactivation of KsgA, a 16S rRNA methyltransferase, causes vigorous emergence of mutants with high-level kasugamycin resistance.,  53  (1): [PMID:19001112] [10.1128/aac.00873-08]

7. Dechy-Cabaret O, Benoit-Vical F..  (2012)  Effects of antimalarial molecules on the gametocyte stage of Plasmodium falciparum: the debate.,  55  (23): [PMID:23075290] [10.1021/jm3005898]

8. NATSUME M, MATSUMOTO M, OHSHIRO A, KOZONE I, HASHIMOTO M, ABE H.  (2003)  Effect of Antibiotics on Formation of Aerial Mycelium and Production of Phytotoxins in Streptomyces spp.,  28  (2): [10.1584/jpestics.28.183]

9. Stevens M, Abdeen S, Salim N, Ray AM, Washburn A, Chitre S, Sivinski J, Park Y, Hoang QQ, Chapman E, Johnson SM..  (2019)  HSP60/10 chaperonin systems are inhibited by a variety of approved drugs, natural products, and known bioactive molecules.,  29  (9): [PMID:30852084] [10.1016/j.bmcl.2019.02.028]

10. Sharma PC, Bansal KK, Sharma A, Sharma D, Deep A..  (2020)  Thiazole-containing compounds as therapeutic targets for cancer therapy.,  188  [PMID:31926469] [10.1016/j.ejmech.2019.112016]

Source

Source(1):

• Scientific Literature