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Limonoids

Description:

Highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Ancestors:

Organic compounds ⮕ Lipids and lipid-like molecules ⮕ Prenol lipids ⮕ Triterpenoids ⮕ Limonoids

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  1. Nimbin
    Nimbin
    CAS: 5945-86-8 PubChem CID: 108058 Formula: C30H36O9 Molecular Weight: 540.6
    ≥98%
    Out of Stock Item #: N1356271
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    Technical Identifiers
    IUPAC Name
    methyl (1S,2R,3R,4R,8R,9S,10R,13R,15R)-2-acetyloxy-13-(furan-3-yl)-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.03,8.01show more
    SMILES
    CC1=C2C(CC1C3=COC=C3)OC4C2(C(C5(C(C4OC(=O)C)C(C=CC5=O)(C)C(=O)OC)C)CC(=O)OC)C
    InChIKey
    NHOIBRJOQAYBJT-IMGVWCFESA-N
    InChI
    1S/C30H36O9/c1-15-18(17-9-11-37-14-17)12-19-23(15)30(5)20(13-22(33)35-6)29(4)21(32)8-10-28(3,27(34)36-7)25(29)24(26(30)39-19)38-16(2)31/h8-11,14,18-20show more
  2. Kihadanin A
    Kihadanin A
    CAS: 125276-62-2 PubChem CID: 180311
    Out of Stock Item #: K1251109
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    Technical Identifiers
    IUPAC Name
    (1R,2R,4S,7R,8S,11R,12R,18R)-7-(2-hydroxy-5-oxo-2H-furan-3-yl)-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.02,4.02,8.012,18]icos-13-ene-5,1show more
    SMILES
    CC1(C2CC(=O)C3(C(C2(C=CC(=O)O1)C)CCC4(C35C(O5)C(=O)OC4C6=CC(=O)OC6O)C)C)C
    InChIKey
    DZWMSKKYNYZQTC-AJLFSXDCSA-N
    InChI
    1S/C26H30O9/c1-22(2)14-11-15(27)25(5)13(23(14,3)8-7-16(28)34-22)6-9-24(4)18(12-10-17(29)32-20(12)30)33-21(31)19-26(24,25)35-19/h7-8,10,13-14,18-20,30Hshow more
  3. Cedrelone
    Cedrelone
    CAS: 1254-85-9 PubChem CID: 21596358
    Out of Stock Item #: C1034154
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    Technical Identifiers
    IUPAC Name
    (1R,2R,4R,6S,7S,10R,11R)-6-(furan-3-yl)-17-hydroxy-1,7,11,15,15-pentamethyl-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadeca-12,16-diene-14,18-dione
    SMILES
    CC1(C(=O)C=CC2(C1=C(C(=O)C3(C2CCC4(C35C(O5)CC4C6=COC=C6)C)C)O)C)C
    InChIKey
    OQMUOVSEPOBWMK-BWLMZZBKSA-N
    InChI
    1S/C26H30O5/c1-22(2)17(27)7-9-23(3)16-6-10-24(4)15(14-8-11-30-13-14)12-18-26(24,31-18)25(16,5)21(29)19(28)20(22)23/h7-9,11,13,15-16,18,28H,6,10,12H2,1show more
  4. Salannin
    Salannin
    CAS: 992-20-1 PubChem CID: 6437066
    ≥99%
    Out of Stock Item #: S1329186
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    Pricing & Pack Sizes
    Technical Identifiers
    IUPAC Name
    [(1R,2S,4R,6R,9R,10R,11R,12S,14R,15R,18R)-14-acetyloxy-6-(furan-3-yl)-10-(2-methoxy-2-oxoethyl)-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.02,9.show more
    SMILES
    CC=C(C)C(=O)OC1CC(C2(COC3C2C1(C(C4(C3OC5C4=C(C(C5)C6=COC=C6)C)C)CC(=O)OC)C)C)OC(=O)C
    InChIKey
    CJHBVBNPNXOWBA-REXVOHEDSA-N
    InChI
    1S/C34H44O9/c1-9-17(2)31(37)43-25-14-24(41-19(4)35)32(5)16-40-28-29(32)33(25,6)23(13-26(36)38-8)34(7)27-18(3)21(20-10-11-39-15-20)12-22(27)42-30(28)34show more
  5. Azadiradione
    Azadiradione
    CAS: 26241-51-0 PubChem CID: 179475 Formula: C28H34O5 Molecular Weight: 450.57
    Out of Stock Item #: A1257689
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    Technical Identifiers
    IUPAC Name
    [(5R,7R,9R,10R,13S,17R)-17-(furan-3-yl)-4,4,8,10,13-pentamethyl-3,16-dioxo-6,7,9,11,12,17-hexahydro-5H-cyclopenta[a]phenanthren-7-yl] acetate
    SMILES
    CC(=O)OC1CC2C(C(=O)C=CC2(C3C1(C4=CC(=O)C(C4(CC3)C)C5=COC=C5)C)C)(C)C
    InChIKey
    KWAMDQVQFVBEAU-BQDUOGPESA-N
    InChI
    1S/C28H34O5/c1-16(29)33-23-14-20-25(2,3)22(31)8-11-26(20,4)19-7-10-27(5)21(28(19,23)6)13-18(30)24(27)17-9-12-32-15-17/h8-9,11-13,15,19-20,23-24H,7,10,show more
  6. no_selection
    Salannal
    CAS: 86160-86-3 PubChem CID: 15226770
    ≥98%
    Out of Stock Item #: S664587
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    Pricing & Pack Sizes
    Technical Identifiers
    IUPAC Name
    [(1S,2R,3R,4S,5R,7S,8R,9R,10R,13R,15R)-2-acetyloxy-4-formyl-13-(furan-3-yl)-5-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-16-oxatetracyclo[show more
    SMILES
    CC=C(C)C(=O)OC1CC(C(C2C1(C(C3(C(C2OC(=O)C)OC4C3=C(C(C4)C5=COC=C5)C)C)CC(=O)OC)C)(C)C=O)O
    InChIKey
    JOVDKZRXWAATEG-REXVOHEDSA-N
    InChI
    1S/C34H44O10/c1-9-17(2)31(39)44-25-14-24(37)32(5,16-35)29-28(42-19(4)36)30-34(7,23(33(25,29)6)13-26(38)40-8)27-18(3)21(12-22(27)43-30)20-10-11-41-15-2show more
  7. 1-Deacetylnimbolinin B
    1-Deacetylnimbolinin B
    CAS: 76689-98-0 PubChem CID: 91895443
    ≥98%
    Out of Stock Item #: D664067
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    Pricing & Pack Sizes
    Technical Identifiers
    IUPAC Name
    [(1R,2R,4R,6S,8R,11R,12S,13R,16R,17R,19S,20R)-17-acetyloxy-8-(furan-3-yl)-4,19-dihydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.02,11.06,10show more
    SMILES
    CC=C(C)C(=O)OC1C2C3C(CO2)(C(CC(C3(C4C1(C5=C(C(CC5OC(C4)O)C6=COC=C6)C)C)C)O)OC(=O)C)C
    InChIKey
    YOBMBNWOJMLHDF-VOYNGPTCSA-N
    InChI
    1S/C33H44O9/c1-8-16(2)30(37)42-29-27-28-31(5,15-39-27)24(40-18(4)34)13-23(35)32(28,6)22-12-25(36)41-21-11-20(19-9-10-38-14-19)17(3)26(21)33(22,29)7/h8show more
  8. Azadirachtin B
    Azadirachtin B
    CAS: 106500-25-8 PubChem CID: 21725521 Formula: C33H42O14 Molecular Weight: 662.68
    ≥99%
    Out of Stock Item #: A650785
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    Pricing & Pack Sizes
    Technical Identifiers
    IUPAC Name
    dimethyl (1S,4S,5R,6S,7S,8R,11S,12R,14S,15R)-7,14-dihydroxy-6-[(1S,2S,6S,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.02,6.09,11]dodecshow more
    SMILES
    CC=C(C)C(=O)OC1CC(C23COC(C2C(C(C4C3C1(CO4)C(=O)OC)O)(C)C56C7CC(C5(O6)C)C8(C=COC8O7)O)C(=O)OC)O
    InChIKey
    USRBWQQLHKQWAV-ZGKQVQOISA-N
    InChI
    1S/C33H42O14/c1-7-14(2)24(36)45-17-11-16(34)30-12-44-20(25(37)40-5)21(30)28(3,23(35)19-22(30)31(17,13-43-19)26(38)41-6)33-18-10-15(29(33,4)47-33)32(39show more
    Synonyms
    AKOS040741190 | HY-133108 | AZADIRACHTIN B(SH) | AZADIRACHTINB(P) | dimethyl (1S,4S,5R,6S,7S,8R,11S,12R,14S,15R)-7,14...
  9. Limonin
    Limonin
    CAS: 1180-71-8 EC Number: 808-129-1 Formula: C26H30O8 Molecular Weight: 470.51
    ≥90%(HPLC) from citrus seeds
    In Stock Item #: L431522
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    Pricing & Pack Sizes
    Technical Identifiers
    IUPAC Name
    (1R,2R,7S,10R,13R,14R,16S,19S,20S)-19-(furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.02,7.02,10.014,16.014,20]docosane-5,12,17-show more
    SMILES
    CC1(C2CC(=O)C3(C(C24COC(=O)CC4O1)CCC5(C36C(O6)C(=O)OC5C7=COC=C7)C)C)C
    InChIKey
    KBDSLGBFQAGHBE-MSGMIQHVSA-N
    InChI
    1S/C26H30O8/c1-22(2)15-9-16(27)24(4)14(25(15)12-31-18(28)10-17(25)33-22)5-7-23(3)19(13-6-8-30-11-13)32-21(29)20-26(23,24)34-20/h6,8,11,14-15,17,19-20Hshow more
    Synonyms
    Limonine | Limonoic acid 3,19:16,17 dilactone | Evodin | Obaculactone | Limonoic acid, di-delta-lactone | Dictamnolac...
  10. Toosendanin
    Toosendanin
    CAS: 58812-37-6 EC Number: 683-199-2 PubChem CID: 9851101 Formula: C30H38O11 Molecular Weight: 574.62
    10mM in DMSO
    In Stock Item #: T424919
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    Pricing & Pack Sizes
    Technical Identifiers
    IUPAC Name
    [(1S,2R,4R,5R,6S,8R,10S,11S,12R,14R,15R,16R,19S,21R)-4-acetyloxy-6-(furan-3-yl)-12,16,19-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3show more
    SMILES
    CC(=O)OC1CC(C23COC(C1(C2CC(C4(C3C(=O)C(C5(C46C(O6)CC5C7=COC=C7)C)OC(=O)C)C)O)C)O)O
    InChIKey
    NAHTXVIXCMUDLF-RFNFAWMESA-N
    InChI
    1S/C30H38O11/c1-13(31)39-20-10-19(34)29-12-38-25(36)26(20,3)17(29)9-18(33)28(5)23(29)22(35)24(40-14(2)32)27(4)16(15-6-7-37-11-15)8-21-30(27,28)41-21/hshow more
    Synonyms
    12-Acetoxyamoorastatin | AKOS025311566 | MFCD00210564 | CHEBI:192461 | Toosendanin | [(1S,2R,4R,5R,6S,8R,10S,11S,12R,...
  11. Obacunone
    Obacunone
    CAS: 751-03-1 Formula: C26H30O7 Molecular Weight: 454.51
    10mM in DMSO
    In Stock Item #: O425830
    View Product
    Pricing & Pack Sizes
    Technical Identifiers
    IUPAC Name
    (1R,2R,4S,7S,8S,11R,12R,18R)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.02,4.02,8.012,18]icos-13-ene-5,15,20-trione
    SMILES
    CC1(C2CC(=O)C3(C(C2(C=CC(=O)O1)C)CCC4(C35C(O5)C(=O)OC4C6=COC=C6)C)C)C
    InChIKey
    MAYJEFRPIKEYBL-OASIGRBWSA-N
    InChI
    1S/C26H30O7/c1-22(2)16-12-17(27)25(5)15(23(16,3)9-7-18(28)32-22)6-10-24(4)19(14-8-11-30-13-14)31-21(29)20-26(24,25)33-20/h7-9,11,13,15-16,19-20H,6,10,show more
    Synonyms
    MLS002473187 | OBACUNON | Z3234884793 | Oxireno(4,4a)-2-benzopyrano(6,5-g)(2)benzoxepin-3,5,9(3aH,4bH,6H)-trione, 1-(...
  12. Nomilin
    Nomilin
    CAS: 1063-77-0 Formula: C28H34O9 Molecular Weight: 514.56
    10mM in DMSO
    In Stock Item #: N420500
    View Product
    Pricing & Pack Sizes
    Technical Identifiers
    IUPAC Name
    [(1R,2R,4S,7S,8S,11R,12R,13S,18R)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-5,15,20-trioxo-3,6,16-trioxapentacyclo[9.9.0.02,4.02,8.012,18]icosan-13-yl] show more
    SMILES
    CC(=O)OC1CC(=O)OC(C2C1(C3CCC4(C(OC(=O)C5C4(C3(C(=O)C2)C)O5)C6=COC=C6)C)C)(C)C
    InChIKey
    KPDOJFFZKAUIOE-WNGDLQANSA-N
    InChI
    1S/C28H34O9/c1-14(29)34-19-12-20(31)36-24(2,3)17-11-18(30)27(6)16(26(17,19)5)7-9-25(4)21(15-8-10-33-13-15)35-23(32)22-28(25,27)37-22/h8,10,13,16-17,19show more
    Synonyms
    CHEBI:7609 | NSC 297134 | AI3-00994 | (1S,3AS,4AR,4BR,6AR,11S,11AR,11BR,13AS)-11-(ACETYLOXY)-1-(3-FURANYL)DECAHYDRO-4...
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