Basic information
- CAS
476-45-9- Standard SMILES
COC1=CC(=O)c2c(O)c(C)c(CC(C)=O)c(O)c2C1=O- InChIKey
UHPMCKVQTMMPCG-UHFFFAOYSA-N- Molecular formula
- C15H14O6
- Average molar mass
- 290.27 g/mol
- Monoisotopic mass
- 290.07903816
Overview
Javanicin is a naphthoquinone.
Names & identifiers
- Preferred name
- Javanicin
- IUPAC
- 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione
- English name
- javanicin
- Molecular formula
- C15H14O6
- Molecular weight
- 290.27
Names & synonyms
JAVANICIN476-45-95,8-Dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dioneJavanicin (Fusarium)HSDB 3501YNR51WFW2RBRN 22960553-Acetonyl-5,8-dihydroxy-6-methoxy-2-methyl-1,4-naphthoquinoneJAVANICIN [MI]JAVANICIN [HSDB]5,8-Dihydroxy-6-methoxy-3-(2-oxopropyl)-1,4-naphthalenedione1,4-Naphthalenedione, 5,8-dihydroxy-6-methoxy-2-methyl-3-(2-oxopropyl)-
Show more names
HSDB3501HSDB-3501Yavanicin
DTXSID409638821,4-Naphthoquinone, 3-acetonyl-5,8-dihydroxy-6-methoxy-2-methyl-4-08-00-03646 (Beilstein Handbook Reference)5,8-Dihydroxy-6-methoxy-2-methyl-3-(2-oxopropyl)-1,4-naphthalenedione1,4-NAPHTHALENEDIONE, 7-ACETONYL-5,8-DIHYDROXY-2-METHOXY-6-METHYL-1,4-NAPHTHALENEDIONE, 5,8-DIHYDROXY-2-METHOXY-6-METHYL-7-(2-OXOPROPYL)-RefChem:792519DTXCID401391608
Database identifiers
- CAS
476-45-9- PubChem CID
- 10149
- DTXSID
Properties
Computed structural properties
- XLogP
- 2
- Topological polar surface area
- 101 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 3
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 508
Experimental & physicochemical properties
SpringerMaterials PropertiesChemical shift
Color/FormRED CRYSTALS WITH COPPERY LUSTER FROM ETHANOL
SolubilitySOL IN ALKALIS
Other Experimental PropertiesDECOMP @ 207.5-208 °C
Physicochemical properties
- Melting point
- 208 °C · 208°C (rough estimate)
- Boiling point
- 352.36 °C · 352.36°C (rough estimate)
- Density
- 1.2451 · 1.2451 (rough estimate)
- refractive index
- 1.4359 · 1.4359 (estimate)
- pka
- 6.88 · 6.88±0.20(Predicted)
- LogP
- 1.51 · 1.510 (est)
- FDA UNII
- 51 WFW2R · YNR51WFW2R
- Hazardous Substances Data
- 476 · 476-45-9(Hazardous Substances Data)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Special ReportsTOXIC EFFECTS & STRUCTURAL FORMULAS ARE DISCUSSED.[KERN H; PHYTOTOXINS PRODUCED BY FUSARIA; PHYTOTOXINS PLANT DIS, PROC NATO ADVAN STUDY INST: 35 (1972)]
Toxicology
InteractionsTHE TOXIC ACTION TO PLANTS WAS REDUCED OR ABOLISHED BY ORGANIC ACIDS (PARTICULARLY GLUTAMIC ACID) & BY METAL IONS (PARTICULARLY COPPER).
Natural Pollution SourcesANTIBIOTIC SUBSTANCE PRODUCED BY FUSARIUM JAVANICUM: ARNSTEIN, COOK, J CHEM SOC 1947, 1021.
Non-Human Toxicity ExcerptsA DOSE OF 60 MG/KG JAVANICIN PRODUCED PHYTOTOXIC EFFECTS IN PEAS & TOMATO PLANTS. 50% ALPHA-DECARBOXYLASE ACTIVITY WAS INHIBITED BY 105X10-6 MOLAR CONCN.
Safety data
- Hazardous Substances Data
- 476-45-9(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Mechanism of Action
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.
Uses & manufacturing
Methods of ManufacturingPREPD BY REDN OF FUSARUBIN: RUELIUS, GAUHE, ANN 569, 38 (1950).
Applications
UsesJavanicin is an antibacterial agent with certain antibacterial activity against pathogenic bacteria such as Bacillus megaterium, Staphylococcus aureus, Salmonella typhi, and Escherichia coli. Javanicin has weak cytotoxicity against the human lung cancer cell line[1].
Upstream & downstream products
Upstream raw materials
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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