Javanicin
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Javanicin
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CAS No:
476-45-9
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Formula:
C15H14O6
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Chemical Name:
Javanicin
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Synonyms:
1,4-Naphthalenedione,5,8-dihydroxy-6-methoxy-2-methyl-3-(2-oxopropyl)-;1,4-Naphthoquinone,3-acetonyl-5,8-dihydroxy-6-methoxy-2-methyl-;Javanicin;5,8-Dihydroxy-6-methoxy-2-methyl-3-(2-oxopropyl)-1,4-naphthalenedione;Javanicin (Fusarium);Yavanicin
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CAS No:
Characteristics
101
1.44700
1.43g/cm3
208 °C (decomp)
616.5ºC at 760 mmHg
235.7ºC
1.622
SOL IN ALKALIS
8.56E-16mmHg at 25°C
DECOMP @ 207.5-208 °C
Safety Information
TOXIC EFFECTS & STRUCTURAL FORMULAS ARE DISCUSSED.[KERN H; PHYTOTOXINS PRODUCED BY FUSARIA; PHYTOTOXINS PLANT DIS, PROC NATO ADVAN STUDY INST: 35 (1972)]
Toxicity
THE TOXIC ACTION TO PLANTS WAS REDUCED OR ABOLISHED BY ORGANIC ACIDS (PARTICULARLY GLUTAMIC ACID) & BY METAL IONS (PARTICULARLY COPPER).
ANTIBIOTIC SUBSTANCE PRODUCED BY FUSARIUM JAVANICUM: ARNSTEIN, COOK, J CHEM SOC 1947, 1021.
Drug Information
JAVANICIN WAS AMONG MOST ACTIVE OF NAPHTHAZARIN DERIVATIVES WHICH INHIBITED ANAEROBIC DECARBOXYLATION OF PYRUVATE IN VITRO CATALYZED BY SACCHAROMYCES CEREVISIAE PYRUVATE DECARBOXYLASE. THE DEGREE OF INHIBITION PARALLELED ANTIFUNGAL ACTIVITY. THIS INHIBITION RESULTED FROM REACTION WITH COENZYME THIAMINE PYROPHOSPHATE & COULD BE PARTIALLY OVERCOME BY EXCESS THIAMINE PYROPHOSPHATE. OXIDATIVE DECARBOXYLATION OF ALPHA-KETOGLUTARATE BY SUSPENSION OF TOMATO MITOCHONDRIA WAS ALSO INHIBITED.
Computed Properties
Molecular Weight:290.27
XLogP3:2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:3
Exact Mass:290.07903816
Monoisotopic Mass:290.07903816
Topological Polar Surface Area:101
Heavy Atom Count:21
Complexity:508
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes