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10140-70-2,MFCD09752718
Catalog No.:AA0004BZ
10140-70-2 | 2H-3-Benzoxacyclododecin-2,10(1H)-dione, 4,5,6,7,8,9-hexahydro-11,13-dihydroxy-4-methyl-, (4S)-
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1mg
≥98%
1 week  
$146.00   $102.00
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5mg
≥98%
1 week  
$403.00   $282.00
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  • Technical Information
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  • Technical Information
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Technical Information
Catalog Number:
AA0004BZ
Chemical Name:
2H-3-Benzoxacyclododecin-2,10(1H)-dione, 4,5,6,7,8,9-hexahydro-11,13-dihydroxy-4-methyl-, (4S)-
CAS Number:
10140-70-2
Molecular Formula:
C16H20O5
Molecular Weight:
292.3270
MDL Number:
MFCD09752718
IUPAC Name:
(5S)-13,15-dihydroxy-5-methyl-4-oxabicyclo[10.4.0]hexadeca-1(12),13,15-triene-3,11-dione
InChI:
InChI=1S/C16H20O5/c1-10-5-3-2-4-6-13(18)16-11(8-15(20)21-10)7-12(17)9-14(16)19/h7,9-10,17,19H,2-6,8H2,1H3/t10-/m0/s1
InChI Key:
VDUIGYAPSXCJFC-JTQLQIEISA-N
SMILES:
C[C@H]1CCCCCC(=O)c2c(CC(=O)O1)cc(O)cc2O
UNII:
WT39K5T3BX
Properties
Computed Properties
 
Complexity:
381  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Defined Bond Stereocenter Count:
0
Exact Mass:
292.131g/mol
Formal Charge:
0
Heavy Atom Count:
21  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
292.331g/mol
Monoisotopic Mass:
292.131g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
83.8A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3.1  

Synonyms
 
10,11-dehydrocurvularin 
curvularin 
CHEMBL478770 
SCHEMBL15256930 
ZINC1649222 
(4S)-4,5,6,7,8,9-Hexahydro-11,13-dihydroxy-4-methyl-2H-3-benzoxacyclododecin-2,10(1H)-dione 
Curvularin, from Penicillium citrinum, >=98% (HPLC) 
(5S)-13,15-dihydroxy-5-methyl-4-oxabicyclo[10.4.0]hexadeca-1(12),13,15-triene-3,11-dione 
2H-3-Benzoxacyclododecin-2,10(1H)-dione, 4,5,6,7,8,9-hexahydro-11,13-dihydroxy-4-methyl-, (4S)- 
2H-3-Benzoxacyclododecin-2,10(1H)-dione, 4,5,6,7,8,9-hexahydro-11,13-dihydroxy-4-methyl-, (S)- (9CI) 
C16H20O5 
AR-1I2772 
Curvularin 
CID119418 
C16-H20-O5 
2H-3-Benzoxacyclododecin-2,10(1H)-dione, 4,5,6,7,8,9-hexahyd 
101931-92-4 
2H-3-benzoxacyclododecin-2,10(1H)-dione, 4,5,6,7,8,9-hexahydro-11,13-dihydroxy-4-methyl- 
2H-3-Benzoxacyclododecin-2,10(1H)-dione, 4,5,6,7,8,9-hexahydro-11,13-dihydroxy-4-methyl-, (S)- 
UNII-WT39K5T3BX 
WT39K5T3BX 
10140-70-2 
(-)-Curvularin 
NSC 166071 
AC1L3OS5 
AC1Q6M97 
Literature

Title: [Biological activity of Penicillium sp. 10-51 exometabolites].

Journal: Mikrobiolohichnyi zhurnal (Kiev, Ukraine : 1993) 20120101

Title: Aryne acyl-alkylation in the general and convergent synthesis of benzannulated macrolactone natural products: an enantioselective synthesis of (-)-curvularin.

Journal: Organic letters 20100402

Title: Transcriptional and post-transcriptional regulation of iNOS expression in human chondrocytes.

Journal: Biochemical pharmacology 20100301

Title: Isolation and difference in anti-Staphylococcus aureus bioactivity of curvularin derivates from fungus Eupenicillium sp.

Journal: Applied biochemistry and biotechnology 20091001

Title: Metabolite production by different Ulocladium species.

Journal: International journal of food microbiology 20080815

Title: Inhibitors of inducible NO synthase expression: total synthesis of (S)-curvularin and its ring homologues.

Journal: ChemMedChem 20080601

Title: First total syntheses and spectral data corrections of 11-alpha-methoxycurvularin and 11-beta-methoxycurvularin.

Journal: The Journal of organic chemistry 20071207

Title: A concise synthetic approach to beta,gamma-dehydrocurvularin: synthesis of (+/-)-di-O-methyl-beta,gamma-dehydrocurvularin.

Journal: Bioscience, biotechnology, and biochemistry 20070601

Title: Microbial transformation of curvularin.

Journal: Journal of natural products 20050801

Title: A new anthraquinone and cytotoxic curvularins of a Penicillium sp. from the rhizosphere of Fallugia paradoxa of the Sonoran desert.

Journal: The Journal of antibiotics 20040501

Title: Betagamma-dehydrocurvularin and related compounds as nematicides of Pratylenchus penetrans from the fungus Aspergillus sp.

Journal: Bioscience, biotechnology, and biochemistry 20030601

Title: Total synthesis of (s)-(+)-citreofuran by ring closing alkyne metathesis.

Journal: The Journal of organic chemistry 20030221

Title: Sporogen, S14-95, and S-curvularin, three inhibitors of human inducible nitric-oxide synthase expression isolated from fungi.

Journal: Molecular pharmacology 20030201

Title: Online analysis of xestodecalactones A-C, novel bioactive metabolites from the fungus Penicillium cf. montanense and their subsequent isolation from the sponge Xestospongia exigua.

Journal: Journal of natural products 20021101

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