Fervenulin
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Hodoodo CAT#: H558185

CAS#: 483-57-8

Description: 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

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Fervenulin
CAS# 483-57-8
Instruction

Theoretical Analysis

Hodoodo Cat#: H558185
Name: Fervenulin
CAS#: 483-57-8
Chemical Formula: C7H7N5O2
Exact Mass: 193.06
Molecular Weight: 193.170
Elemental Analysis: C, 43.53; H, 3.65; N, 36.26; O, 16.57

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Synonym: Fervenulin; 10204-Bii; Planomycin; 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:

Biological target:
In vitro activity:
In vivo activity:

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.

Recalculate based on batch purity %
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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Esipov SE, Chernyshev AI, Shorshnev SV, Iakushkina NI, Antonovskiĭ VL. [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. PubMed PMID: 4004184.

2: 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. PubMed PMID: 21841897; PubMed Central PMCID: PMC3128717.

3: 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. PubMed PMID: 13815215.

4: Aleksandrov GG, Esipov SE. [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. PubMed PMID: 3717915.

5: 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. PubMed PMID: 3415453.

6: EBLE TE, OLSON EC, LARGE CM, SHELL JW. Fervenulin, a new crystalline antibiotic. II. Isolation and characterization. Antibiot Annu. 1959-1960;7:227-9. PubMed PMID: 13819172.

7: 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. PubMed PMID: 1177058.

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. PubMed PMID: 4472132.

9: 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. PubMed PMID: 789854.

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. PubMed PMID: 27073352; PubMed Central PMCID: PMC4819732.

11: 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. PubMed PMID: 18776503.