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Substance Name: Pactamycin
RN: 23668-11-3
UNII: 18P04J5471
InChIKey: WVIUOSJLUCTGFK-JUJPXXQGSA-N

Note

  • Antibiotic produced by Streptomyces pactum used as an antineoplastic agent. It is also used as a tool in biochemistry because it inhibits certain steps in protein synthesis.

Molecular Formula

  • C28-H38-N4-O8

Molecular Weight

  • 558.6282
 

Classification Codes

  • Antibiotics, Antineoplastic
  • Antineoplastic Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Mutation Data
  • Natural Product
  • Protein Synthesis Inhibitors
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Names and Synonyms

Name of Substance

  • Pactamycin

MeSH Heading

  • Pactamycin

Synonyms

  • (5-((3-Acetylphenyl)amino)-4-amino-3-(((dimethylamino)carbonyl)amino)-1,2-dihydroxy-3-(1-hydroxyethyl)-2-methylcyclopentyl)methyl 2-hydroxy-6-methylbenzoate (1S-(1alpha,2beta,3alpha,3(R*),4alpha,5beta))-
  • AI3-51038
  • NSC 52947
  • NSC-52947
  • Pactamycin
  • SK 27773
  • U 15800
  • U-15800
  • UNII-18P04J5471
  • Upjohn culture 135bt

Systematic Names

  • 2,6-Cresotic acid, monoester with 3-(4-(m-acetylanilino)-5-amino-2,3-dihydroxy-1-(1-hydroxyethyl)-2-(hydroxymethyl)-3-methylcyclopentyl)-1,1-dimethylurea(VAN) (8CI)
  • Benzoic acid, 2-hydroxy-6-methyl-, (3-((3-acetylphenyl)amino)-4-amino-5-(((dimethylamino)carbonyl)amino)-1,2-dihydroxy-5-(1-hydroxyethyl)-2-methylcyclopentyl)methyl ester
  • Benzoic acid, 2-hydroxy-6-methyl-, (5-((3-acetylphenyl)amino)-4-amino-3-(((dimethylamino)carbonyl)amino)-1,2-dihydroxy-3-(1-hydroxyethyl)-2-methylcyclopentyl)methyl ester, (1S-(1alpha,2beta,3alpha,3(R*),4alpha,5beta))-
  • Pactamycin

Registry Numbers

CAS Registry Number

  • 23668-11-3

FDA UNII

  • 18P04J5471

Other Registry Numbers

  • 1405-46-5
  • 30999-13-4
  • 886995-63-7

System Generated Number

  • 0023668113

Structure Descriptors

InChI

1S/C28H38N4O8/c1-15-9-7-12-20(35)21(15)24(36)40-14-27(39)23(30-19-11-8-10-18(13-19)16(2)33)22(29)28(17(3)34,26(27,4)38)31-25(37)32(5)6/h7-13,17,22-23,30,34-35,38-39H,14,29H2,1-6H3,(H,31,37)/t17-,22-,23-,26-,27+,28-/m0/s1

InChIKey

WVIUOSJLUCTGFK-JUJPXXQGSA-N

Smiles

C[C@H](O)[C@]1(NC(=O)N(C)C)[C@@H](N)[C@H](Nc2cccc(c2)C(=O)C)[C@](O)(COC(=O)c3c(C)cccc3O)[C@]1(C)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo unreported 750ug/kg (0.75mg/kg) GASTROINTESTINAL: OTHER CHANGES

BEHAVIORAL: FOOD INTAKE (ANIMAL)

LIVER: OTHER CHANGES
Antimicrobial Agents and Chemotherapy Vol. -, Pg. 184, 1961.
mouse LD50 intraperitoneal 14mg/kg (14mg/kg)   Toxicology and Applied Pharmacology. Vol. 31, Pg. 208, 1975.
mouse LD50 intravenous 15600ug/kg (15.6mg/kg) BEHAVIORAL: FOOD INTAKE (ANIMAL)

LIVER: OTHER CHANGES

GASTROINTESTINAL: OTHER CHANGES
Antimicrobial Agents and Chemotherapy Vol. -, Pg. 184, 1961.
mouse LD50 oral 10mg/kg (10mg/kg)   "Compounds Available for Fundamental Research, Volume II-6, Antibiotics, A Program of Upjohn Company Research Laboratory." Vol. 2(6), Pg. -, 1971.
rat LD50 intravenous 1400ug/kg (1.4mg/kg) BEHAVIORAL: FOOD INTAKE (ANIMAL)

GASTROINTESTINAL: OTHER CHANGES

LIVER: OTHER CHANGES
Antimicrobial Agents and Chemotherapy Vol. -, Pg. 184, 1961.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) 0.880 (none)   EST
Atmospheric OH Rate Constant 1.57E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.