(-)-Curvularin
Basic information
- CAS
10140-70-2- Standard SMILES
C[C@H]1CCCCCC(=O)c2c(O)cc(O)cc2CC(=O)O1- InChIKey
VDUIGYAPSXCJFC-JTQLQIEISA-N- Molecular formula
- C16H20O5
- Average molar mass
- 292.33 g/mol
- Monoisotopic mass
- 292.13107373
Overview
(5S)-13,15-dihydroxy-5-methyl-4-oxabicyclo[10.4.0]hexadeca-1(12),13,15-triene-3,11-dione has been reported in Penicillium citreonigrum, Penicillium sumatraense, and other organisms with data available.
Names & identifiers
- Preferred name
- (-)-Curvularin
- IUPAC
- (5S)-13,15-dihydroxy-5-methyl-4-oxabicyclo[10.4.0]hexadeca-1(12),13,15-triene-3,11-dione
- English name
- curvularin
- Molecular formula
- C16H20O5
- Molecular weight
- 292.33
Names & synonyms
Curvularin10140-70-2WT39K5T3BXDTXSID001017585(4S)-4,5,6,7,8,9-Hexahydro-11,13-dihydroxy-4-methyl-2H-3-benzoxacyclododecin-2,10(1H)-dioneNSC-166071(-)-CurvularinRefChem:905545DTXCID401475769(S)-Curvularin(5S)-13,15-dihydroxy-5-methyl-4-oxabicyclo[10.4.0]hexadeca-1(12),13,15-triene-3,11-dione2H-3-Benzoxacyclododecin-2,10(1H)-dione, 4,5,6,7,8,9-hexahydro-11,13-dihydroxy-4-methyl-, (4S)-
Show more names
S-Curvularin, NSC 166071Curvularin, Antibiotic agent2H-3-Benzoxacyclododecin-2,10(1H)-dione, 4,5,6,7,8,9-hexahydro-11,13-dihydroxy-4-methyl-,(4S)-Curvularin/(S)-11,13-Dihydroxy-4-methyl-4,5,6,7,8,9-hexahydro-2H-benzo[d][1]oxacyclododecine-2,10(1H)-dione
2H-3-Benzoxacyclododecin-2,10(1H)-dione, 4,5,6,7,8,9-hexahydro-11,13-dihydroxy-4-methyl-, (S)-UNII-WT39K5T3BXNSC 166071CURVULARIN [MI]CHEMBL478770orb1989686SCHEMBL15256930SCHEMBL29928932
Properties
Computed structural properties
- XLogP
- 3.1
- Topological polar surface area
- 83.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 0
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 381
Physicochemical properties
- Melting point
- 206 · 206-206.5°
- alpha
- 18 · D18 -36.3° (c = 3.8 in ethanol)
- Boiling point
- 557 · 557.0±29.0 °C(Predicted)
- Density
- 1.2 · 1.200±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- 1 mg/mL · DMSO: soluble1mg/mL
- form
- powder
- pka
- 7.58 · 7.58±0.40(Predicted)
- color
- Off-white
- FDA UNII
- 39 K5T3BX · WT39K5T3BX
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
- Precautionary statements
- 264 · P264-P270-P301+P312-P330-P501
- Hazard Codes
- Xn
- Risk Statements
- 22 · 22
- WGK Germany
- 3 · 3
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- wgk
- 3
- hs_code
- 29419000
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- Hazard statements
- H302
- Precautionary statements
- P264-P270-P301+P312-P330-P501
Chemistry & industry
Applications
UsesCurvularin is a 12-membered macrocyclic lactone incorporating a resorcinyl moiety, produced by a number of fungal species, including Curvularia, Penicillium and Alternaria. Curvularin exhibits a distinctly different biological profile to the structurally similar resorcylic acid lactones such as the zearalenones, radicicol and LL Z1640-2. Curvularin inhibits cell division by disrupting mitotic spindle formation and is known to be phytotoxic. More recent investigations have shown that curvularin is a highly selective transcription-based inhibitor of iNOS-dependent NO production, acting on the Janus tyrosine kinase-STAT pathway. This action offers an approach to the development of drugs inhibiting iNOS overproduction associated with NO pathophysiology.
UsesCurvularin is a potent antifungal and mycotoxin that also inhibits NO production.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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