Thiazomycin

ID: ALA506017

Chembl Id: CHEMBL506017

PubChem CID: 16156566

Max Phase: Preclinical

Molecular Formula: C61H58N14O18S5

Molecular Weight: 1435.55

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: Thiazomycin | Thiazomycin|CHEBI:66219|CHEMBL506017|SCHEMBL14192134|Q27134757|2-[(E)-[(3aR,4S,6S,7aS)-3,4,7a-trimethyl-3a,4,6,7-tetrahydro-2H-pyrano[3,4-d]oxazol-6-yl]oxy-dihydroxy-[(1R)-1-hydroxyethyl]-(1-methoxyethylidene)-hexaoxo-[?]yl]-N-(1-carbamoylvinyl)thiazole-4-carboxamide

Canonical SMILES:  C=C(NC(=O)c1csc(-c2nc3c(cc2O)-c2nc(cs2)C(=O)N[C@@H]([C@@H](C)O)C(=O)N/C(=C(\C)OC)c2nc(cs2)C(=O)N[C@@H]2c4nc(cs4)C(=O)N[C@@H](COC(=O)c4c5c6c(cccc6n4O)COC(=O)[C@@H](O[C@H]4C[C@]6(C)OCN(C)[C@@H]6[C@H](C)O4)[C@H]2OC5)c2nc-3cs2)n1)C(N)=O

Standard InChI:  InChI=1S/C61H58N14O18S5/c1-22(48(62)78)63-49(79)31-18-97-57(68-31)42-36(77)11-27-41(70-42)30-16-95-55(65-30)29-15-90-59(84)44-28-14-88-45(46(60(85)89-13-26-9-8-10-35(38(26)28)75(44)86)93-37-12-61(5)47(25(4)92-37)74(6)21-91-61)43(58-69-32(19-98-58)50(80)64-29)73-52(82)34-20-96-56(67-34)40(24(3)87-7)72-53(83)39(23(2)76)71-51(81)33-17-94-54(27)66-33/h8-11,16-20,23,25,29,37,39,43,45-47,76-77,86H,1,12-15,21H2,2-7H3,(H2,62,78)(H,63,79)(H,64,80)(H,71,81)(H,72,83)(H,73,82)/b40-24+/t23-,25+,29+,37+,39+,43+,45+,46+,47-,61+/m1/s1

Standard InChI Key:  GYOHFSLEKIIJMU-UMNFMQIXSA-N

Alternative Forms

  1. Parent:

    ALA506017

    THIAZOMYCIN

Associated Targets(non-human)

Streptococcus pneumoniae (31063 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Enterococcus faecalis (29875 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Staphylococcus aureus (210822 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Haemophilus influenzae (8812 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Escherichia coli (133304 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Candida albicans (78123 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Staphylococcus haemolyticus (1695 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Staphylococcus epidermidis (22802 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Enterococcus faecium (13803 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Streptococcus pyogenes (16140 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Clostridioides difficile (2968 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Bacteroides fragilis (1445 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

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 1435.55Molecular Weight (Monoisotopic): 1434.2657AlogP: #Rotatable Bonds:
Polar Surface Area: Molecular Species: HBA: HBD:
#RO5 Violations: HBA (Lipinski): HBD (Lipinski): #RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: CX LogP: CX LogD:
Aromatic Rings: Heavy Atoms: QED Weighted: Np Likeness Score:

References

1. Zhang C, Zink DL, Ushio M, Burgess B, Onishi R, Masurekar P, Barrett JF, Singh SB..  (2008)  Isolation, structure, and antibacterial activity of thiazomycin A, a potent thiazolyl peptide antibiotic from Amycolatopsis fastidiosa.,  16  (19): [PMID:18804380] [10.1016/j.bmc.2008.08.079]
2. Zhang C, Herath K, Jayasuriya H, Ondeyka JG, Zink DL, Occi J, Birdsall G, Venugopal J, Ushio M, Burgess B, Masurekar P, Barrett JF, Singh SB..  (2009)  Thiazomycins, thiazolyl peptide antibiotics from Amycolatopsis fastidiosa.,  72  (5): [PMID:19334707] [10.1021/np800783b]
3. Singh SB, Miesel L, Kramer S, Xu L, Li F, Lan J, Lipari P, Polishook JD, Liu G, Liang L, Flattery AM..  (2022)  Nocathiacin, Thiazomycin, and Polar Analogs Are Highly Effective Agents against Toxigenic Clostridioides difficile.,  85  (4.0): [PMID:35380836] [10.1021/acs.jnatprod.2c00093]

Source