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Substance Name: Leinamycin
RN: 120500-15-4
InChIKey: ZHTRILQJTPJGNK-GZTIPBDCSA-N

Note

  • A thiazole containing macrolide characterized by an unusual 1,3-dioxo-1,2-dithiolane moiety that is spiro fused to an 18 member macrolactam ring; isolated from Streptomyces; possible DNA alkylator; the leinamycin biosynthetic gene cluster from Streptomyces atroolivaceus S-140 consists of two polyketide synthases genes.

Molecular Formula

  • C22-H26-N2-O6-S3

Molecular Weight

  • 510.653
 

Classification Codes

  • Drug / Therapeutic Agent
  • Natural Product
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Names and Synonyms

Name of Substance

  • Leinamycin

Synonyms

  • (+)-Leinamycin
  • Antibiotic DC 107
  • DC 107
  • Leinamycin

Systematic Name

  • Spiro(1,2-dithiolane-3,6'-(19)thia(3,20)diazabicyclo(15.2.1)eicosa(1(20),9,13,15,17)pentaene)-4',5,12'-trione, 4,11'-dihydroxy-2',4,9'-trimethyl-, 2-oxide

Registry Numbers

CAS Registry Number

  • 120500-15-4

System Generated Number

  • 0120500154

Structure Descriptors

InChI

1S/C22H26N2O6S3/c1-13-8-9-22(21(3,29)20(28)32-33(22)30)11-18(27)23-14(2)19-24-15(12-31-19)6-4-5-7-16(25)17(26)10-13/h4-7,10,12,14,17,26,29H,8-9,11H2,1-3H3,(H,23,27)/b6-4-,7-5-,13-10-

InChIKey

ZHTRILQJTPJGNK-GZTIPBDCSA-N

Smiles

S1[S@@]([C@@]2([C@@](C1=O)(C)O)CC(N[C@@H](c1scc(C=CC=CC([C@@H](C=C(CC2)C)O)=O)n1)C)=O)=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 2800ug/kg (2.8mg/kg)   Journal of Antibiotics. Vol. 42, Pg. 333, 1989.