Skip Navigation
ChemIDplus A TOXNET DATABASE LiteBrowseAdvanced

Substance Name: Verruculogen
RN: 12771-72-1
InChIKey: LRXYHMMJJCTUMY-GWXUGYLUSA-N

Note

  • Complex 6-O-methylindole cpd containing 3 nitrogens; induces tremor; tremorigenic metabolite from Penicillium verruculosum isolated from moldy peanuts; decreases GABA levels in CNS.

Classification Codes

  • Mutation Data
  • Natural Product

Molecular Formula

  • C27-H33-N3-O7

Molecular Weight

  • 511.5717
 
* denotes mobile formatted website

Links to Resources


Search for this InChIKey on the Web

Names and Synonyms

Name of Substance

  • Verruculogen

Synonyms

  • TR1
  • Verruculogen
  • Verruculogen TR 1

Systematic Names

  • (5R-(5alpha,10 alpha,10aalpha,14aalpha,15balpha))-1,10,10a,14,14a,15b-Hexahydro-10,10a-dihydroxy-7-methoxy-2,2-dimethyl-5-(2-methyl-1-propenyl)-5H,12H-3,4-dioxa-5a,11a,15a-triaza cyclooct (1m) indeno (5,6-b)fluorene-11,15(2H,13H)-dione
  • 5H,12H-3,4-Dioxa-5a,11a,15a-triazacyclooct(lm)indeno(5,6-b)fluorene-11,15(2H,13H)-dione, 1,10,10a,14,14a,15b-hexahydro-10,10a-dihydroxy-7-methoxy-2,2-dimethyl-5-(2-methyl-1-propenyl)-, (5R,10S,10aR,14aS,15bS)-
  • 5H,12H-3,4-Dioxa-5a,11a,15a-triazacyclooct(lm)indeno(5,6-b)fluorene-11,15(2H,13H)-dione, 1,10,10a,14,14a,15b-hexahydro-10,10a-dihydroxy-7-methoxy-2,2-dimethyl-5-(2-methyl-1-propenyl)-,(5R-(5-alpha,10-alpha,10a-alpha,14a-alpha-15b-alpha))-

Registry Numbers

CAS Registry Number

  • 12771-72-1

System Generated Number

  • 0012771721

Structure Descriptors

InChI

1S/C27H33N3O7/c1-14(2)11-20-29-18-12-15(35-5)8-9-16(18)21-22(29)19(13-26(3,4)37-36-20)30-24(32)17-7-6-10-28(17)25(33)27(30,34)23(21)31/h8-9,11-12,17,19-20,23,31,34H,6-7,10,13H2,1-5H3/t17-,19-,20+,23-,27+/m0/s1

InChIKey

LRXYHMMJJCTUMY-GWXUGYLUSA-N

Smiles

COc1ccc2c3[C@H](O)[C@]4(O)N([C@H]5CC(C)(C)OO[C@H](C=C(C)C)n(c35)c2c1)C(=O)[C@@H]6CCCN6C4=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
chicken LD50 intraperitoneal 15200ug/kg (15.2mg/kg)   Journal of Antibiotics. Vol. 41, Pg. 1868, 1988.
chicken LD50 oral 266mg/kg (266mg/kg)   Journal of Antibiotics. Vol. 41, Pg. 1868, 1988.
mouse LD50 intraperitoneal 2400ug/kg (2.4mg/kg)   Journal of Antibiotics. Vol. 41, Pg. 1868, 1988.
mouse LD50 oral 127mg/kg (127mg/kg)   Journal of Antibiotics. Vol. 41, Pg. 1868, 1988.
mouse LD50 unreported 2400ug/kg (2.4mg/kg)   "Toxicology, Biochemistry and Pathology of Mycotoxins," Uraguchi, K. and M. Yamazaki, eds., New York, John Wiley & Sons, Inc., 1978Vol. -, Pg. 108, 1978.