Fervenulin | CAS#483-57-8 | Nematocidal bacterial metabolite

MedKoo Cat#: 558185 | Name: Fervenulin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Fervenulin is a bacterial metabolite originally isolated from Streptomyces that has nematocidal activity. It inhibits egg hatching of the root-knot nematode M. incognita (MIC = 30 µg/ml), as well as induces mortality in M. incognita second-stage juveniles when used at a concentration of 250 µg/ml.

Chemical Structure

Fervenulin

CAS#483-57-8

Theoretical Analysis

MedKoo Cat#: 558185

Name: Fervenulin

CAS#: 483-57-8

Chemical Formula: C7H7N5O2

Exact Mass: 193.0600

Molecular Weight: 193.17

Elemental Analysis: C, 43.53; H, 3.65; N, 36.26; O, 16.57

Price and Availability

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5mg	USD 450.00	Back order

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Related CAS #

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Synonym

Fervenulin; Planomycin; Fervenuline; Pulanomycin; 10204-Bii; KC 1017; KC1017; KC-1017; NSC 68158; NSC68158; NSC-68158; U 7118; U7118; U-7118;

IUPAC/Chemical Name

6,8-Dimethylpyrimido(5,4-e)-as-triazine-5,7(6H,8H)dione

InChi Key

RRTKVYSLIGQWCO-UHFFFAOYSA-N

InChi Code

InChI=1S/C7H7N5O2/c1-11-5-4(8-3-9-10-5)6(13)12(2)7(11)14/h3H,1-2H3

SMILES Code

O=C(C1=C2N=NC=N1)N(C)C(N2C)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 193.17 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Wang H, Hu L, Chang X, Hu Y, Zhang Y, Zhou P, Cui X. Determination of bacterial toxin toxoflavin and fervenulin in food and identification of their degradation products. Food Chem. 2023 Jan 15;399:134010. doi: 10.1016/j.foodchem.2022.134010. Epub 2022 Aug 27. PMID: 36058099. 2: Su C, Yan Y, Guo X, Luo J, Liu C, Zhang Z, Xiang WS, Huang SX. Characterization of the N-methyltransferases involved in the biosynthesis of toxoflavin, fervenulin and reumycin from Streptomyces hiroshimensis ATCC53615. Org Biomol Chem. 2019 Jan 16;17(3):477-481. doi: 10.1039/c8ob02847h. PMID: 30565634. 3: Ruanpanun P, Laatsch H, Tangchitsomkid N, Lumyong S. Nematicidal activity of fervenulin isolated from a nematicidal actinomycete, Streptomyces sp. CMU-MH021, on Meloidogyne incognita. World J Microbiol Biotechnol. 2011 Jun;27(6):1373-80. doi: 10.1007/s11274-010-0588-z. Epub 2010 Oct 22. PMID: 21841897; PMCID: PMC3128717. 4: Taylor EC, Sowinski F. Synthesis of the pyrimido [5,4-e]-as-triazine antibiotics fervenulin and 2-methylfevenulone. J Org Chem. 1975 Aug 8;40(16):2321-29. doi: 10.1021/jo00904a013. PMID: 1177058. 5: EBLE TE, OLSON EC, LARGE CM, SHELL JW. Fervenulin, a new crystalline antibiotic. II. Isolation and characterization. Antibiot Annu. 1959-1960;7:227-9. PMID: 13819172. 6: Coburn RA, Carapellotti RA. Synthesis and properties of mesoionic pyrimido[1,2-b-a1pyridazine-2,4-diones and mesoionic pyridazino[2,3-a-a1-s-trizine-2,4-diones: mesoionic analogs structurally related to fervenulin. J Pharm Sci. 1976 Oct;65(10):1505-10. doi: 10.1002/jps.2600651022. PMID: 789854. 7: DEBOER C, DIETZ A, EVANS JS, MICHAELS RM. Fervenulin, a new crystalline antibiotic. I. Discovery and biological activities. Antibiot Annu. 1959-1960;7:220-6. PMID: 13815215. 8: Clark J, Morton MS. Heterocyclic studies. XXXV. Cleavage of fervenulin and 3-methyl-fervenulin by nucleophiles. J Chem Soc Perkin 1. 1974;0(15):1818-23. doi: 10.1039/p19740001818. PMID: 4472132. 9: Jäckel H, Stamm H. Molecular complexes, 9. Arene complexes of fervenulin, an antibiotic structurally related to caffeine. Formation constants and complex topologies determined by the refined 1H-NMR shift method. Arch Pharm (Weinheim). 1988 Apr;321(4):213-9. doi: 10.1002/ardp.19883210408. PMID: 3415453. 10: Wu C, Zhu H, van Wezel GP, Choi YH. Metabolomics-guided analysis of isocoumarin production by Streptomyces species MBT76 and biotransformation of flavonoids and phenylpropanoids. Metabolomics. 2016;12:90. doi: 10.1007/s11306-016-1025-6. Epub 2016 Mar 30. PMID: 27073352; PMCID: PMC4819732. 11: Aleksandrov GG, Esipov SE. Rentgenostrukturnoe issledovanie pirimido-[5,4-e]-1,2,4-triazinovykh antibiotikov ksantotritsina i fervenulina [X-ray structural study of the pyrimido-[5,4-e]-1,2,4-triazine antibiotics xanthothricin and fervenulin]. Antibiot Med Biotekhnol. 1986 Mar;31(3):181-4. Russian. PMID: 3717915. 12: Esipov SE, Chernyshev AI, Shorshnev SV, Iakushkina NI, Antonovskiĭ VL. Izuchenie ustoĭchivosti pirimido-[5,4-e]-1,2,4-triazinovykh antibiotikov v kislotno-osnovnykh sredakh metodom spektroskopii IaMR [Study of the stability of pyrimido-[5,4-e]-1,2,4-triazine antibiotics in acid-base media by NMR spectroscopy]. Antibiot Med Biotekhnol. 1985 Feb;30(2):122-4. Russian. PMID: 4004184. 13: Nagamatsu T, Ma J, Akiba S. Regioselective glycosylation of 7-azapteridines and conversion of the 7-azapteridine nucleosides into 6-azapurine nucleosides. Nucleic Acids Symp Ser (Oxf). 2008;(52):561-2. doi: 10.1093/nass/nrn284. PMID: 18776503.