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Tigliane and ingenane diterpenoids

Description:

Diterpenoids containing the tigliane or ingenane carbon skeleton. The tigliane skeleton is a tetracyclic ring that consists of the 4/7/6/3 ring junction. It is derived from casbane by 6,10- and 5,14-cyclizations and is a framework of phorbol. The ingenane skeleton is derived by rearrangement of tigliane.

Ancestors:

Organic compounds ⮕ Lipids and lipid-like molecules ⮕ Prenol lipids ⮕ Diterpenoids ⮕ Tigliane and ingenane diterpenoids

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  1. Ingenol Mebutate
    Ingenol Mebutate
    CAS: 75567-37-2 EC Number: 688-125-2 PubChem CID: 6918670 Formula: C25H34O6 Molecular Weight: 430.53
    ≥98%
    Out of Stock Item #: I769904
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    Technical Identifiers
    IUPAC Name
    [(1S,4S,5S,6R,9S,10R,12R,14R)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxo-4-tetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dienyl] (Z)-2show more
    SMILES
    CC=C(C)C(=O)OC1C(=CC23C1(C(C(=CC(C2=O)C4C(C4(C)C)CC3C)CO)O)O)C
    InChIKey
    VDJHFHXMUKFKET-WDUFCVPESA-N
    InChI
    1S/C25H34O6/c1-7-12(2)22(29)31-21-13(3)10-24-14(4)8-17-18(23(17,5)6)16(20(24)28)9-15(11-26)19(27)25(21,24)30/h7,9-10,14,16-19,21,26-27,30H,8,11H2,1-6Hshow more
  2. no_selection
    12-O-Tiglylphorbol-13 –isobutyrate
    CAS: 92214-54-5 PubChem CID: 73350378
    ≥98%
    Out of Stock Item #: O664057
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    Technical Identifiers
    IUPAC Name
    [(1S,2S,6R,10S,11R,13S,14R,15R)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-13-(2-methylpropanoyloxy)-5-oxo-14-tetracyclo[8.5.0.02,6.011,13show more
    SMILES
    CC=C(C)C(=O)OC1C(C2(C(C=C(CC3(C2C=C(C3=O)C)O)CO)C4C1(C4(C)C)OC(=O)C(C)C)O)C
    InChIKey
    MVWXLRYZCZSBKW-RXYGMQKRSA-N
    InChI
    1S/C29H40O8/c1-9-15(4)25(33)36-23-17(6)28(35)19(21-26(7,8)29(21,23)37-24(32)14(2)3)11-18(13-30)12-27(34)20(28)10-16(5)22(27)31/h9-11,14,17,19-21,23,30show more
  3. 4α-PDH - , used for , CAS No. P607179, by Aladdin Scientific
    4α-PDH
    Moligand™ ? Moligand™ — Aladdin's line of ligands and bioactive small molecules. Use for receptor, pathway, and binding studies needing defined small-molecule tools.
    Out of Stock Item #: P607179
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    IUPAC Name
    (1S,2S,6S,10S,11R,13S,14R,15R)-14-(hexanoyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeshow more
    SMILES
    CCCCCC(=O)O[C@@H]1[C@@H](C)[C@@]2(O)[C@H]([C@H]3[C@]1(OC(=O)CCCCC)C3(C)C)C=C(C[C@@]1([C@H]2C=C(C1=O)C)O)CO
    InChIKey
    XGPRSRGBAHBMAF-QYSBVNMQSA-N
    InChI
    1S/C32H48O8/c1-7-9-11-13-24(34)39-28-20(4)31(38)22(16-21(18-33)17-30(37)23(31)15-19(3)27(30)36)26-29(5,6)32(26,28)40-25(35)14-12-10-8-2/h15-16,20,22-2show more
    Synonyms
    4α-phorbol 12,13-dihexanoate
  4. Ingenol
    Ingenol
    CAS: 30220-46-3 Formula: C20H28O5 Molecular Weight: 348.43
    10mM in DMSO
    In Stock Item #: I580420
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    Technical Identifiers
    IUPAC Name
    (1S,4S,5R,6R,9S,10R,12R,14R)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dien-15-one
    SMILES
    CC1CC2C(C2(C)C)C3C=C(C(C4(C1(C3=O)C=C(C4O)C)O)O)CO
    InChIKey
    VEBVPUXQAPLADL-POYOOMFHSA-N
    InChI
    1S/C20H28O5/c1-9-7-19-10(2)5-13-14(18(13,3)4)12(17(19)24)6-11(8-21)16(23)20(19,25)15(9)22/h6-7,10,12-16,21-23,25H,5,8H2,1-4H3/t10-,12+,13-,14+,15+,16-show more
    Synonyms
    ingenol|30220-46-3|(1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1a,2,5,5a,6...
  5. Phorbol
    Phorbol
    CAS: 17673-25-5 EC Number: 634-015-4 Formula: C20H28O6 Molecular Weight: 364.43
    10mM in DMSO
    In Stock Item #: P422154
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    Technical Identifiers
    IUPAC Name
    (1S,2S,6R,10S,11R,13S,14R,15R)-1,6,13,14-tetrahydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyltetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dien-5-one
    SMILES
    CC1C(C2(C(C2(C)C)C3C1(C4C=C(C(=O)C4(CC(=C3)CO)O)C)O)O)O
    InChIKey
    QGVLYPPODPLXMB-UBTYZVCOSA-N
    InChI
    1S/C20H28O6/c1-9-5-13-18(24,15(9)22)7-11(8-21)6-12-14-17(3,4)20(14,26)16(23)10(2)19(12,13)25/h5-6,10,12-14,16,21,23-26H,7-8H2,1-4H3/t10-,12+,13-,14-,1show more
    Synonyms
    AC-33956 | (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-1,1a,1b,4,4a...
  6. Phorbol
    Phorbol
    CAS: 17673-25-5 Formula: C20H28O6 Molecular Weight: 364.43
    ≥98%
    In Stock Item #: P333869
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    Pricing & Pack Sizes
    Technical Identifiers
    IUPAC Name
    (1S,2S,6R,10S,11R,13S,14R,15R)-1,6,13,14-tetrahydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyltetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dien-5-one
    SMILES
    CC1C(C2(C(C2(C)C)C3C1(C4C=C(C(=O)C4(CC(=C3)CO)O)C)O)O)O
    InChIKey
    QGVLYPPODPLXMB-UBTYZVCOSA-N
    InChI
    1S/C20H28O6/c1-9-5-13-18(24,15(9)22)7-11(8-21)6-12-14-17(3,4)20(14,26)16(23)10(2)19(12,13)25/h5-6,10,12-14,16,21,23-26H,7-8H2,1-4H3/t10-,12+,13-,14-,1show more
    Synonyms
    AC-33956 | (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-1,1a,1b,4,4a...
  7. Ingenol
    Ingenol
    CAS: 30220-46-3 Formula: C20H28O5 Molecular Weight: 348.43
    ≥98%
    In Stock Item #: I140089
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    Pricing & Pack Sizes
    Technical Identifiers
    IUPAC Name
    (1S,4S,5R,6R,9S,10R,12R,14R)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dien-15-one
    SMILES
    CC1CC2C(C2(C)C)C3C=C(C(C4(C1(C3=O)C=C(C4O)C)O)O)CO
    InChIKey
    VEBVPUXQAPLADL-POYOOMFHSA-N
    InChI
    1S/C20H28O5/c1-9-7-19-10(2)5-13-14(18(13,3)4)12(17(19)24)6-11(8-21)16(23)20(19,25)15(9)22/h6-7,10,12-16,21-23,25H,5,8H2,1-4H3/t10-,12+,13-,14+,15+,16-show more
    Synonyms
    CHEBI:5922 | SCHEMBL17691258 | (1S,4S,5R,6R,9S,10R,12R,14R)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl...
  8. 20-O-Acetylingenol-3-angelate
    20-O-Acetylingenol-3-angelate
    CAS: 82425-35-2 PubChem CID: 9934504 Formula: C27H36O7 Molecular Weight: 472.57
    ≥98%
    Out of Stock Item #: A398818
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    Technical Identifiers
    IUPAC Name
    [(1S,4S,5S,6R,9S,10R,12R,14R)-7-(acetyloxymethyl)-5,6-dihydroxy-3,11,11,14-tetramethyl-15-oxo-4-tetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dienyl] (Z)show more
    SMILES
    CC=C(C)C(=O)OC1C(=CC23C1(C(C(=CC(C2=O)C4C(C4(C)C)CC3C)COC(=O)C)O)O)C
    InChIKey
    ZYCAGKYWXRKLSN-KLKWOBOISA-N
    InChI
    1S/C27H36O7/c1-8-13(2)24(31)34-23-14(3)11-26-15(4)9-19-20(25(19,6)7)18(22(26)30)10-17(12-33-16(5)28)21(29)27(23,26)32/h8,10-11,15,18-21,23,29,32H,9,12show more
  9. 20-Deoxyingenol - 98%, used for , CAS No. 54706-99-9, by Aladdin Scientific
    20-Deoxyingenol
    CAS: 54706-99-9 PubChem CID: 11290503 Formula: C20H28O4 Molecular Weight: 332.43
    ≥98%
    In Stock Item #: D334325
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    Pricing & Pack Sizes
    Technical Identifiers
    IUPAC Name
    (1S,4S,5S,6R,9S,10R,12R,14R)-4,5,6-trihydroxy-3,7,11,11,14-pentamethyltetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dien-15-one
    SMILES
    CC1CC2C(C2(C)C)C3C=C(C(C4(C1(C3=O)C=C(C4O)C)O)O)C
    InChIKey
    FOSYZKSOJUQLTD-NHPMXQBPSA-N
    InChI
    1S/C20H28O4/c1-9-6-12-14-13(18(14,4)5)7-11(3)19(17(12)23)8-10(2)16(22)20(19,24)15(9)21/h6,8,11-16,21-22,24H,7H2,1-5H3/t11-,12+,13-,14+,15-,16+,19+,20+show more
    Synonyms
    [1aR(1aα,2β,5β,5aβ,6β,8aα,9α,10aα)]-1a,2,5,5a,6,9,10,10a-Octahydro-5,5a,6-trihydroxy-1,1,4,7,9-pentamethyl1H-2,8a-Met...
  10. 20-Deoxyingenol
    20-Deoxyingenol
    CAS: 54706-99-9 PubChem CID: 11290503 Formula: C20H28O4 Molecular Weight: 332.43
    10mM in DMSO
    In Stock Item #: D424661
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    Pricing & Pack Sizes
    Technical Identifiers
    IUPAC Name
    (1S,4S,5S,6R,9S,10R,12R,14R)-4,5,6-trihydroxy-3,7,11,11,14-pentamethyltetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dien-15-one
    SMILES
    CC1CC2C(C2(C)C)C3C=C(C(C4(C1(C3=O)C=C(C4O)C)O)O)C
    InChIKey
    FOSYZKSOJUQLTD-NHPMXQBPSA-N
    InChI
    1S/C20H28O4/c1-9-6-12-14-13(18(14,4)5)7-11(3)19(17(12)23)8-10(2)16(22)20(19,24)15(9)21/h6,8,11-16,21-22,24H,7H2,1-5H3/t11-,12+,13-,14+,15-,16+,19+,20+show more
  11. 13-Oxyingenol dodecanoat
    13-Oxyingenol dodecanoat
    CAS: 54706-70-6 PubChem CID: 85364165 Formula: C32H50O7 Molecular Weight: 546.74
    ≥98%
    Out of Stock Item #: O398802
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    Pricing & Pack Sizes
    Technical Identifiers
    IUPAC Name
    [(1S,4S,5R,6R,9S,10R,12S,14R)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxo-12-tetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dienyl] dshow more
    SMILES
    CCCCCCCCCCCC(=O)OC12CC(C34C=C(C(C3(C(C(=CC(C1C2(C)C)C4=O)CO)O)O)O)C)C
    InChIKey
    FEZDDYPHEHMXLF-YFQQJSGYSA-N
    InChI
    1S/C32H50O7/c1-6-7-8-9-10-11-12-13-14-15-24(34)39-31-18-21(3)30-17-20(2)26(35)32(30,38)27(36)22(19-33)16-23(28(30)37)25(31)29(31,4)5/h16-17,21,23,25-2show more
  12. Phorbol 12,13-dibutyrate - ≥98% CAS No(37558-16-0) by Aladdin Scientific
    Phorbol 12,13-dibutyrate
    CAS: 37558-16-0 EC Number: 636-433-2 PubChem CID: 37783 Formula: C28H40O8 Molecular Weight: 504.61
    Solid Moligand™ ? Moligand™ — Aladdin's line of ligands and bioactive small molecules. Use for receptor, pathway, and binding studies needing defined small-molecule tools. ≥98%
    In Stock Item #: P276207
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    Pricing & Pack Sizes
    Technical Identifiers
    IUPAC Name
    [(1S,2S,6R,10S,11R,13S,14R,15R)-13-butanoyloxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-show more
    SMILES
    CCCC(=O)OC1C(C2(C(C=C(CC3(C2C=C(C3=O)C)O)CO)C4C1(C4(C)C)OC(=O)CCC)O)C
    InChIKey
    BQJRUJTZSGYBEZ-YVQNUNKESA-N
    InChI
    1S/C28H40O8/c1-7-9-20(30)35-24-16(4)27(34)18(22-25(5,6)28(22,24)36-21(31)10-8-2)12-17(14-29)13-26(33)19(27)11-15(3)23(26)32/h11-12,16,18-19,22,24,29,3show more
    Synonyms
    Butanoic acid, (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1...
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