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Substance Name: Paldimycin A
RN: 101411-70-5
UNII: 7HMD7M29RI
InChIKey: UZGZVADYRITDOQ-OWVLXQSESA-N

Note

  • Semi-synthetic antibiotic from Streptomyces paulus.

Classification Code

  • Drug / Therapeutic Agent

Molecular Formula

  • C44-H64-N4-O23-S3

Molecular Weight

  • 1113.19
 
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Names and Synonyms

Name of Substance

  • Paldimycin A

Synonyms

  • 2-Amino-5-(3-O-(2,6-dideoxy-4-C-((1S)-1-hydroxyethyl)-3-O-methyl-alpha-L-lyxo-hexopyranosyl)-beta-D-allopyranosyl)-5-hydroxy-3,6-dioxo-1-cyclohexene-1-carboxylic acid, 4'-(3-(((2R)-2-acetamido-2-carboxyethyl)thio)-2-((dithiocarboxy)amino)butyrate), 6'-acetate, 4''-C-((2S)-2-methylbutyrate), S-ester with N-acetyl-L-cysteine
  • 2-Amino-5-(3-O-(2,6-dideoxy-4-C-((1S)-1-hydroxyethyl)-3-O-methyl-alpha-L-lyxo-hexopyranosyl)-beta-D-allopyranosyl)-5-hydroxy-3,6-dioxo-1-cyclohexene-1-carboxylic acid, 4'-(3-(((2R)-2-acetamido-2-carboxyethyl)thio)-2-((dithiocarboxy)amino)butyrate), 6'-acetate, 4'-C-((2S)-2-methylbutyrate), S-ester with N-acetyl-L-cysteine
  • Antibiotic 273 A1-alpha
  • L-Cysteine, N-acetyl-, (2-((2-(acetylamino)-2-carboxyethyl)thio)-1-carboxypropyl)carbamodithioate(ester), 4'-ester with 5-(6-O-acetyl-3-O-(2,6-dideoxy-3-O-methyl-4-C-(1-(2-methyl-1-oxobutoxy)ethyl)-alpha-L-lyxo-hexopyranosyl)-beta-D-allopyranosyl)-2-amino-5-hydroxy-3,6-dioxo-1-cyclohexene-1-carboxylic acid
  • Paldimycin A
  • UNII-7HMD7M29RI

Systematic Names

  • L-Cysteine, N-acetyl-, (2-((2-(acetylamino)-2-carboxyethyl)thio)-1-carboxypropyl)carbamodithioate (ester), 4'-ester with 5-(6-O-acetyl-3-O-(2,6-dideoxy-3-O-methyl-4-C-(1-(2-methyl-1-oxobutoxy)ethyl)-alpha-L-lyxo-hexopyranosyl)-beta-D-allopyranosyl)-2-amino-5-hydroxy-3,6-hydroxy-3,6-dioxo-1-cyclohexene-1-carboxylic acid
  • L-Cysteine, N-acetyl-, (2-((2-(acetylamino)-2-carboxyethyl)thio)-1-carboxypropyl)carbamodithioate(ester), 4'-ester with 5-(6-O-acetyl-3-O-(2,6-dideoxy-3-O-methyl-4-C-(1-(2-methyl-1-oxobutoxy)ethyl)-alpha-L-lyxo-hexopyranosyl)-beta-D-allopyranosyl)-2-amino-5-hydroxy-3,6-dioxo-1-cyclohexene-1-carboxylic acid

Registry Numbers

CAS Registry Number

  • 101411-70-5

FDA UNII

  • 7HMD7M29RI

Other Registry Number

  • 94555-00-7

System Generated Number

  • 0101411705

Structure Descriptors

InChI

1S/C44H64N4O23S3/c1-10-16(2)40(61)68-19(5)44(64)18(4)67-28(11-27(44)65-9)70-34-32(53)36(43(63)12-25(52)30(45)29(35(43)54)39(59)60)69-26(13-66-22(8)51)33(34)71-41(62)31(17(3)73-14-23(37(55)56)46-20(6)49)48-42(72)74-15-24(38(57)58)47-21(7)50/h16-19,23-24,26-28,31-34,36,53,63-64H,10-15,45H2,1-9H3,(H,46,49)(H,47,50)(H,48,72)(H,55,56)(H,57,58)(H,59,60)/t16-,17?,18-,19-,23-,24-,26+,27-,28?,31?,32+,33+,34-,36+,43+,44-/m0/s1

InChIKey

UZGZVADYRITDOQ-OWVLXQSESA-N

Smiles

O([C@@H]1[C@@H]([C@H](O[C@H]([C@@H]1O)[C@@]1(C(C(=C(N)C(C1)=O)C(O)=O)=O)O)COC(C)=O)OC([C@@H]([C@@H](SC[C@H](NC(C)=O)C(O)=O)C)NC(SC[C@H](NC(C)=O)C(O)=O)=S)=O)[C@@H]1C[C@@H]([C@]([C@@H](OC([C@H](CC)C)=O)C)(O)[C@@H](O1)C)OC

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal > 3gm/kg (3000mg/kg)   Journal of Antibiotics. Vol. 40, Pg. 419, 1987.