Guaianolides and derivatives

Description:

Diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Ancestors:

Organic compounds ⮕ Lipids and lipid-like molecules ⮕ Prenol lipids ⮕ Terpene lactones ⮕ Sesquiterpene lactones ⮕ Guaianolides and derivatives

Epoxymicheliolide
- ≥98%
Cas Number: 1343403-10-0 Compound CID: 71490387

IUPAC Name: (1R,3S,6S,10S,11S,12R)-12-hydroxy-3,12-dimethyl-7-methylidene-2,9-dioxatetracyclo[9.3.0.01,3.06,10]tetradecan-8-one

SMILES: CC1(CCC23C1C4C(CCC2(O3)C)C(=C)C(=O)O4)O

InChIKey: IFWNFKWDSMXFLK-NCWRXGJMSA-N

InChI: InChI=1S/C15H20O4/c1-8-9-4-5-14(3)15(19-14)7-6-13(2,17)11(15)10(9)18-12(8)16/h9-11,17H,1,4-7H2,2-3H3/t9-,10-,11-,13+,14-,15+/m0/s1
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Eupalinilide D
- ≥98%
Cas Number: 757202-14-5 Compound CID: 11347578

IUPAC Name: (3aR,4R,6R,6aS,7R,9aR,9bR)-6-(chloromethyl)-4,6,7-trihydroxy-9-methyl-3-methylidene-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one

SMILES: CC1=CC(C2C1C3C(C(CC2(CCl)O)O)C(=C)C(=O)O3)O

InChIKey: JNRJLCSYIQFLDS-DKLFCYGSSA-N

InChI: InChI=1S/C15H19ClO5/c1-6-3-8(17)12-10(6)13-11(7(2)14(19)21-13)9(18)4-15(12,20)5-16/h3,8-13,17-18,20H,2,4-5H2,1H3/t8-,9-,10+,11-,12-,13-,15+/m1/s1
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Eupalinilide C
- ≥98%
Cas Number: 757202-11-2 Compound CID: 11417523

IUPAC Name: [(1R,2R,6R,7R,9R,12R,15S)-9-hydroxy-14-methyl-5-methylidene-4-oxo-3,11-dioxatetracyclo[7.5.1.02,6.012,15]pentadec-13-en-7-yl] (E)-4-hydroxy-2-methylbushow more

SMILES: CC1=CC2C3C1C4C(C(CC3(CO2)O)OC(=O)C(=CCO)C)C(=C)C(=O)O4

InChIKey: QWNQZWRFKIHTPL-NPUYJLKLSA-N

InChI: InChI=1S/C20H24O7/c1-9(4-5-21)18(22)26-13-7-20(24)8-25-12-6-10(2)14(16(12)20)17-15(13)11(3)19(23)27-17/h4,6,12-17,21,24H,3,5,7-8H2,1-2H3/b9-4+/t12-,13show more
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Cynaropicrin
- ≥98%
Cas Number: 35730-78-0 Compound CID: 119093

Formula: C₁₉H₂₂O₆ Molecular Weight: 346.37

IUPAC Name: [(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate

SMILES: C=C1CC(C2C(C3C1CC(C3=C)O)OC(=O)C2=C)OC(=O)C(=C)CO

InChIKey: KHSCYOFDKADJDJ-NQLMQOPMSA-N

InChI: InChI=1S/C19H22O6/c1-8-5-14(24-18(22)9(2)7-20)16-11(4)19(23)25-17(16)15-10(3)13(21)6-12(8)15/h12-17,20-21H,1-7H2/t12-,13-,14-,15-,16+,17+/m0/s1

Synonyms: MEGxp0_001095 | A901510 | NCGC00168845-02 | DTXSID20957143 | 2-PROPENOIC ACID, 2-(HYDROXYMETHYL)-, DODECAHYDRO-8-HYDR...
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grosheimin
Cas Number: 22489-66-3 Compound CID: 442256

IUPAC Name: (3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-9-methyl-3,6-dimethylidene-3a,4,5,6a,7,9,9a,9b-octahydroazuleno[4,5-b]furan-2,8-dione

SMILES: C[C@H]1[C@H]2[C@@H](CC1=O)C(=C)C[C@@H]([C@@H]3[C@@H]2OC(=O)C3=C)O

InChIKey: YGMIBVIKXJJQQJ-MSOSQAFRSA-N

InChI: InChI=1S/C15H18O4/c1-6-4-11(17)13-8(3)15(18)19-14(13)12-7(2)10(16)5-9(6)12/h7,9,11-14,17H,1,3-5H2,2H3/t7-,9+,11+,12+,13-,14-/m1/s1

Synonyms: 4-beta-H-Guaia-10(14),11(13)-dien-12-oic acid, 6-alpha,8-alpha-dihydroxy-3-oxo-, 12,6-lactone | 4betaH-GUAIA-10(14),1...
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Dehydrocostus lactone
- 10mM in DMSO
Cas Number: 477-43-0

Formula: C₁₅H₁₈O₂ Molecular Weight: 230.31

IUPAC Name: (3aS,6aR,9aR,9bS)-3,6,9-trimethylidene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one

SMILES: C=C1CCC2C(C3C1CCC3=C)OC(=O)C2=C

InChIKey: NETSQGRTUNRXEO-XUXIUFHCSA-N

InChI: InChI=1S/C15H18O2/c1-8-4-7-12-10(3)15(16)17-14(12)13-9(2)5-6-11(8)13/h11-14H,1-7H2/t11-,12-,13-,14-/m0/s1

Synonyms: Dehydrocostus lactone|477-43-0|dehydrocostuslactone|Epiligulyl oxide|(-)-dehydrocostus lactone|71TRF5K040|(-)-dehydro...
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Arglabin
- ≥98%
Cas Number: 84692-91-1

Formula: C₁₅H₁₈O₃ Molecular Weight: 246.31

IUPAC Name: (1R,3S,6S,10S,11R)-3,12-dimethyl-7-methylidene-2,9-dioxatetracyclo[9.3.0.01,3.06,10]tetradec-12-en-8-one

SMILES: CC1=CCC23C1C4C(CCC2(O3)C)C(=C)C(=O)O4

InChIKey: UVJYAKBJSGRTHA-CUZKYEQNSA-N

InChI: InChI=1S/C15H18O3/c1-8-4-7-15-11(8)12-10(9(2)13(16)17-12)5-6-14(15,3)18-15/h4,10-12H,2,5-7H2,1,3H3/t10-,11+,12-,14-,15+/m0/s1

Synonyms: (1R,3S,6S,10S,11R)-3,12-dimethyl-7-methylidene-2,9-dioxatetracyclo[9.3.0.0?,?.0?,??]tetradec-12-en-8-one | BDBM504334...
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Dehydrocostus lactone
Cas Number: 477-43-0

Formula: C₁₅H₁₈O₂ Molecular Weight: 230.31

IUPAC Name: (3aS,6aR,9aR,9bS)-3,6,9-trimethylidene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one

SMILES: C=C1CCC2C(C3C1CCC3=C)OC(=O)C2=C

InChIKey: NETSQGRTUNRXEO-XUXIUFHCSA-N

InChI: InChI=1S/C15H18O2/c1-8-4-7-12-10(3)15(16)17-14(12)13-9(2)5-6-11(8)13/h11-14H,1-7H2/t11-,12-,13-,14-/m0/s1

Synonyms: dehydrocostuslactone | (3aS,6aR,9aR,9bS)-3,6,9-trimethylidene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one ...
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