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Substance Name: Valinomycin
RN: 2001-95-8
UNII: N561YS75MN
InChIKey: FCFNRCROJUBPLU-DNDCDFAISA-N

Note

  • A cyclododecadepsipeptide ionophore antibiotic produced by Streptomyces fulvissimus and related to the enniatins. It is composed of 3 moles each of L-valine, D-alpha-hydroxyisovaleric acid, D-valine, and L-lactic acid linked alternately to form a 36-membered ring. (From Merck Index, 11th ed) Valinomycin is a potassium selective ionophore and is commonly used as a tool in biochemical studies.

Molecular Formula

  • C54-H90-N6-O18

Molecular Weight

  • 1111.329
 

Classification Codes

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Drug / Therapeutic Agent
  • Ionophores
  • Membrane Transport Modulators
  • Natural Product

Superlist Classification Code

  • Threshold Planning Quantity (TPQ) = 1000/10000 lb
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Names and Synonyms

Name of Substance

  • Valinomycin

MeSH Heading

  • Valinomycin

Synonyms

  • 1,7,13,19,25,31-Hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriacontane- 2,5,8,11,14,17,20,23,26,29,32,35-dodecone, 12,24,36-trimetyl-3,6,9,15,18,21,27,30,33-nonakis(1-methylethyl)-
  • 4-27-00-09728 (Beilstein Handbook Reference)
  • Antibiotic N-329 B
  • BRN 0078657
  • Cyclic(D-alpha-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl-D-alpha-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl-D-alpha-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl)
  • EINECS 217-896-6
  • HSDB 6423
  • NSC 122023
  • Potassium ionophore I
  • UNII-N561YS75MN
  • Valinomicin
  • Valinomycin

Systematic Name

  • Valinomycin

Superlist Name

  • Valinomycin

Registry Numbers

CAS Registry Number

  • 2001-95-8

FDA UNII

  • N561YS75MN

Other Registry Numbers

  • 11005-80-4
  • 134-16-7
  • 32398-05-3

System Generated Number

  • 0002001958

Structure Descriptors

InChI

1S/C54H90N6O18/c1-22(2)34-49(67)73-31(19)43(61)55-38(26(9)10)53(71)77-41(29(15)16)47(65)59-36(24(5)6)51(69)75-33(21)45(63)57-39(27(11)12)54(72)78-42(30(17)18)48(66)60-35(23(3)4)50(68)74-32(20)44(62)56-37(25(7)8)52(70)76-40(28(13)14)46(64)58-34/h22-42H,1-21H3,(H,55,61)(H,56,62)(H,57,63)(H,58,64)(H,59,65)(H,60,66)/t31-,32-,33-,34+,35+,36+,37-,38-,39-,40+,41+,42+/m0/s1

InChIKey

FCFNRCROJUBPLU-DNDCDFAISA-N

Smiles

CC(C)[C@@H]1NC(=O)[C@H](C)OC(=O)[C@H](NC(=O)[C@H](OC(=O)[C@@H](NC(=O)[C@H](C)OC(=O)[C@H](NC(=O)[C@H](OC(=O)[C@@H](NC(=O)[C@H](C)OC(=O)[C@H](NC(=O)[C@H](OC1=O)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 390ug/kg (0.39mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse LD50 intravenous 180ug/kg (0.18mg/kg)   Cancer Research. Vol. 46, Pg. 5518, 1986.
mouse LD50 oral 2500ug/kg (2.5mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 325, 1978.
mouse LD50 subcutaneous 4140ug/kg (4.14mg/kg)   Antibiotics and Chemotherapy Vol. 12, Pg. 482, 1962.
rabbit LD50 skin 5mg/kg (5mg/kg)   Drug and Chemical Toxicology. Vol. 8, Pg. 451, 1985.
rabbit LD50 skin 5mg/kg (5mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: TREMOR
Drug and Chemical Toxicology. Vol. 8, Pg. 451, 1985.
rat LD50 intraperitoneal 800ug/kg (0.8mg/kg)   Drug and Chemical Toxicology. Vol. 8, Pg. 451, 1985.
rat LD50 intraperitoneal 800ug/kg (0.8mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Drug and Chemical Toxicology. Vol. 8, Pg. 451, 1985.
rat LD50 oral 4mg/kg (4mg/kg)   Drug and Chemical Toxicology. Vol. 8, Pg. 451, 1985.
rat LD50 oral 4mg/kg (4mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: TREMOR
Drug and Chemical Toxicology. Vol. 8, Pg. 451, 1985.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 190 deg C   EXP
log P (octanol-water) 4.490 (none)   EST
Atmospheric OH Rate Constant 1.08E-10 cm3/molecule-sec 25 EST

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