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Substance Name: Basifungin [USAN:INN]
RN: 127785-64-2
UNII: VV0USO6I6U
InChIKey: RLMLFADXHJLPSQ-QKCBWMAHSA-N

Note

  • Inositol phosphorylceramide synthase inhibitor; isolated from the culture medium of Aureobasidium pullulans R 106.

Molecular Formula

  • C60-H92-N8-O11

Molecular Weight

  • 1101.4318
 

Classification Codes

  • Anti-Infective Agents
  • Antifungal
  • Antifungal Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Natural Product
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Names and Synonyms

Name of Substance

  • Aureobasidin A
  • Basifungin [USAN:INN]
  • LY 295337

Synonyms

  • Antibiotic R106I
  • Aureobasidin A
  • Basifungin
  • LY 295337
  • LY295337
  • N-((2R,3R)-2-Hydroxy-3-methylvaleryl)-N-methyl-L-valyl-L-phenylalanyl-N-methyl-L-phenylalanyl-L-prolyl-L-alloisoleucyl-N-methyl-L-valyl-L-leucyl-3-hydroxy-N-methyl-L-valine alpha1-lactone
  • NK 204
  • R106-1
  • UNII-VV0USO6I6U

Systematic Names

  • Aureobasidin A
  • Valine, 3-hydroxy-N-(N-(N-(N-(1-(N-(N-(N-(2-hydroxy-3-methyl-1-oxopentyl)-N-methylvalyl)phenylalanyl)-N-methylphenylalanyl)prolyl)alloisoleucyl)-N-methylvalyl)leucyl)-N-methyl-, alpha-1-lactone

Registry Numbers

CAS Registry Number

  • 127785-64-2

FDA UNII

  • VV0USO6I6U

System Generated Number

  • 0127785642

Structure Descriptors

InChI

1S/C60H92N8O11/c1-17-38(9)46-57(75)65(14)47(36(5)6)52(70)61-42(32-35(3)4)55(73)67(16)50(60(11,12)78)59(77)79-49(39(10)18-2)58(76)66(15)48(37(7)8)53(71)62-43(33-40-26-21-19-22-27-40)54(72)64(13)45(34-41-28-23-20-24-29-41)56(74)68-31-25-30-44(68)51(69)63-46/h19-24,26-29,35-39,42-50,78H,17-18,25,30-34H2,1-16H3,(H,61,70)(H,62,71)(H,63,69)/t38-,39-,42+,43+,44+,45+,46+,47+,48+,49-,50-/m1/s1

InChIKey

RLMLFADXHJLPSQ-QKCBWMAHSA-N

Smiles

CC[C@@H](C)[C@H]1C(=O)N([C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)O[C@@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)N2CCC[C@H]2C(=O)N1)Cc3ccccc3)C)Cc4ccccc4)C(C)C)C)[C@H](C)CC)C(C)(C)O)C)CC(C)C)C(C)C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1gm/kg (1000mg/kg)   Journal of Antibiotics. Vol. 46, Pg. 1414, 1993.
mouse LD50 intravenous 231mg/kg (231mg/kg)   Journal of Antibiotics. Vol. 46, Pg. 1414, 1993.
mouse LD50 oral > 1gm/kg (1000mg/kg)   United States Patent Document. Vol. #5158876,
mouse LD50 subcutaneous > 1gm/kg (1000mg/kg)   Journal of Antibiotics. Vol. 46, Pg. 1414, 1993.