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Withanolides and derivatives

Description:

C28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring.

Ancestors:

Organic compounds ⮕ Lipids and lipid-like molecules ⮕ Steroids and steroid derivatives ⮕ Steroid lactones ⮕ Withanolides and derivatives
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9 Items

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  1. Withanolide B
      Grade & Purity: 
    • ≥98%
    Cas Number: 56973-41-2        EC Number: 685-416-6        Compound CID:  14236711
    Formula:  C28H38O5        Molecular Weight: 454.60
    IUPAC Name:  (1S,2S,4S,5R,10R,11S,14R,15R,18S)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4show more
    SMILES:  CC1=C(C(=O)OC(C1)C(C)C2CCC3C2(CCC4C3C5C(O5)C6(C4(C(=O)C=CC6)C)O)C)C
    InChIKey: ZTEVDTFJUUJBLP-MBMSZCMESA-N
    InChI:  InChI=1S/C28H38O5/c1-14-13-20(32-25(30)15(14)2)16(3)17-8-9-18-22-19(10-12-26(17,18)4)27(5)21(29)7-6-11-28(27,31)24-23(22)33-24/h6-7,16-20,22-24,31H,8-show more
    Synonyms: Lycium substance B | CS-0106690 | DTXSID20205575 | (5.ALPHA.,6.ALPHA.,7.ALPHA.,22R)-5-HYDROXY-6,7:22,26-DIEPOXYERGOST...
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  2. Taccalonolide A
      Grade & Purity: 
    • ≥99%
    Cas Number: 108885-68-3        Compound CID:  441685
    Formula:  C36H46O14        Molecular Weight: 702.74
    IUPAC Name:  [(1S,2S,3R,5S,7S,9S,10R,11R,12S,13S,14R,15R,16S,17S,22S,23S,24R,25R)-10,14,25-triacetyloxy-3,22-dihydroxy-11,15,17,22,23-pentamethyl-4,21-dioxo-8,20-dshow more
    SMILES:  CC1C=C2C(C3C1C4(C(C3OC(=O)C)C5C(C(C4OC(=O)C)OC(=O)C)C6(C(CC7C(C6OC(=O)C)O7)C(=O)C5O)C)C)(C(C(=O)O2)(C)O)C
    InChIKey: PTTJLTMUKRRHAT-VJAKQJMOSA-N
    InChI:  InChI=1S/C36H46O14/c1-12-10-19-35(8,36(9,44)32(43)50-19)24-21(12)34(7)22(28(24)45-13(2)37)20-23(29(46-14(3)38)31(34)48-16(5)40)33(6)17(25(41)26(20)42)show more
    Synonyms: A904550 | CHEBI:9388 | AKOS037515195 | 16,24-Cycloergost-22-en-26-oicacid, 1,11,12,15-tetrakis(acetyloxy)-2,3-epoxy-7...
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  3. Dihydrowithaferin A
      Grade & Purity: 
    • ≥99%
    Cas Number: 5589-41-3        Compound CID:  418033
    Formula:  C28H40O6        Molecular Weight: 472.61
    IUPAC Name:  6-hydroxy-15-[1-[5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-3-one
    SMILES:  CC1=C(C(=O)OC(C1)C(C)C2CCC3C2(CCC4C3CC5C6(C4(C(=O)CCC6O)C)O5)C)CO
    InChIKey: YRXCLNDPESBJHL-UHFFFAOYSA-N
    InChI:  InChI=1S/C28H40O6/c1-14-11-21(33-25(32)17(14)13-29)15(2)18-5-6-19-16-12-24-28(34-24)23(31)8-7-22(30)27(28,4)20(16)9-10-26(18,19)3/h15-16,18-21,23-24,2show more
    Synonyms: DTXSID10329178 | NSC328417 | NSC-328417 | NSC97867 | NSC-97867 | DihydrowithaferinA | FT-0775740 | 2,3-Dihydrowithafe...
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  4. Withanolide A
      Grade & Purity: 
    • ≥98%
    Cas Number: 32911-62-9        Compound CID:  11294368
    Formula:  C28H38O6        Molecular Weight: 470.6
    IUPAC Name:  (1S,2S,4S,5R,10R,11S,14S,15S,18S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[show more
    SMILES:  CC1=C(C(=O)OC(C1)C(C)(C2CCC3C2(CCC4C3C5C(O5)C6(C4(C(=O)C=CC6)C)O)C)O)C
    InChIKey: DXWHOKCXBGLTMQ-SFQAJKIESA-N
    InChI:  InChI=1S/C28H38O6/c1-14-13-20(33-24(30)15(14)2)27(5,31)18-9-8-16-21-17(10-12-25(16,18)3)26(4)19(29)7-6-11-28(26,32)23-22(21)34-23/h6-7,16-18,20-23,31-show more
    Synonyms: Withanolide A, (+)- | Q27291676 | (5.ALPHA.,6.ALPHA.,7.ALPHA.,22R)-5,20-DIHYDROXY-6,7:22,26-DIEPOXYERGOSTA-2,24-DIENE...
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  5. Withanoside IV
      Grade & Purity: 
    • ≥95%
    Cas Number: 362472-81-9        Compound CID:  71312551
    Formula:  C40H62O15        Molecular Weight: 782.91
    IUPAC Name:  (2R)-2-[(1S)-1-[(1S,3R,8S,9S,10R,13S,14S,17R)-1-hydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hshow more
    SMILES:  CC1=C(C(=O)OC(C1)C(C)C2CCC3C2(CCC4C3CC=C5C4(C(CC(C5)OC6C(C(C(C(O6)COC7C(C(C(C(O7)CO)O)O)O)O)O)O)O)C)C)CO
    InChIKey: VUQQGHSDHGOYRH-IFUSOADVSA-N
    InChI:  InChI=1S/C40H62O15/c1-17-11-26(53-36(50)22(17)14-41)18(2)23-7-8-24-21-6-5-19-12-20(13-29(43)40(19,4)25(21)9-10-39(23,24)3)52-38-35(49)33(47)31(45)28(5show more
    Synonyms: (1α,3β,22R)-3-[(6-O-β-D-Glucopyranosyl-β-D-glucopyranosyl)oxy]-1,22,27-trihydroxy-ergosta-5,24-dien-26-oic acid δ-lac...
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  6. Withaferin A
    Cas Number: 5119-48-2        Compound CID:  265237
    Formula:  C28H38O6        Molecular Weight: 470.6
    IUPAC Name:  (1S,2R,6S,7R,9R,11S,12S,15R,16S)-6-hydroxy-15-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclshow more
    SMILES:  CC1=C(C(=O)OC(C1)C(C)C2CCC3C2(CCC4C3CC5C6(C4(C(=O)C=CC6O)C)O5)C)CO
    InChIKey: DBRXOUCRJQVYJQ-CKNDUULBSA-N
    InChI:  InChI=1S/C28H38O6/c1-14-11-21(33-25(32)17(14)13-29)15(2)18-5-6-19-16-12-24-28(34-24)23(31)8-7-22(30)27(28,4)20(16)9-10-26(18,19)3/h7-8,15-16,18-21,23-show more
    Synonyms: NSC273757 | NSC-273757 | WITHAFERIN A [MI] | NCGC00180796-02_C28H38O6_(4beta,5beta,6beta,22R)-4,27-Dihydroxy-5,6:22,2...
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  7. Withaferin A
      Grade & Purity: 
    • ≥98%(HPLC)
    Cas Number: 5119-48-2        Compound CID:  265237
    Formula:  C28H38O6        Molecular Weight: 470.6
    IUPAC Name:  (1S,2R,6S,7R,9R,11S,12S,15R,16S)-6-hydroxy-15-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclshow more
    SMILES:  CC1=C(C(=O)OC(C1)C(C)C2CCC3C2(CCC4C3CC5C6(C4(C(=O)C=CC6O)C)O5)C)CO
    InChIKey: DBRXOUCRJQVYJQ-CKNDUULBSA-N
    InChI:  InChI=1S/C28H38O6/c1-14-11-21(33-25(32)17(14)13-29)15(2)18-5-6-19-16-12-24-28(34-24)23(31)8-7-22(30)27(28,4)20(16)9-10-26(18,19)3/h7-8,15-16,18-21,23-show more
    Synonyms: NSC273757 | NSC-273757 | WITHAFERIN A [MI] | NCGC00180796-02_C28H38O6_(4beta,5beta,6beta,22R)-4,27-Dihydroxy-5,6:22,2...
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  8. Withanone
    Cas Number: 27570-38-3        Compound CID:  21679027
    Formula:  C28H38O6        Molecular Weight: 470.6
    IUPAC Name:  (1S,2S,4S,5R,10R,11S,14S,15S,18S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-5,15-dihydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0show more
    SMILES:  CC1=C(C(=O)OC(C1)C(C)C2(CCC3C2(CCC4C3C5C(O5)C6(C4(C(=O)C=CC6)C)O)C)O)C
    InChIKey: FAZIYUIDUNHZRG-PCTWTJKKSA-N
    InChI:  InChI=1S/C28H38O6/c1-14-13-19(33-24(30)15(14)2)16(3)27(31)12-9-17-21-18(8-11-25(17,27)4)26(5)20(29)7-6-10-28(26,32)23-22(21)34-23/h6-7,16-19,21-23,31-show more
    Synonyms: AKOS040762509 | CS-0107490 | DTXSID40950237 | 15-[1-(4,5-Dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-5,15-dihydroxy-1...
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  9. 12-Deoxywithastramonolide
    Cas Number: 60124-17-6
    Formula:  C28H38O6        Molecular Weight: 470.6
    IUPAC Name:  (1S,2S,4S,5R,10R,11S,14R,15R,18S)-5-hydroxy-15-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-10,14-dimethyl-3-oxapentacyshow more
    SMILES:  CC1=C(C(=O)OC(C1)C(C)C2CCC3C2(CCC4C3C5C(O5)C6(C4(C(=O)C=CC6)C)O)C)CO
    InChIKey: AWVMHXZWAKRDGG-MEBIVHGNSA-N
    InChI:  InChI=1S/C28H38O6/c1-14-12-20(33-25(31)16(14)13-29)15(2)17-7-8-18-22-19(9-11-26(17,18)3)27(4)21(30)6-5-10-28(27,32)24-23(22)34-24/h5-6,15,17-20,22-24,show more
    Synonyms: XD164984 | CHEBI:183967 | Baimantuoluoside C | 27-Hydroxywithanolide B | HY-N7195 | MS-28703 | 12-Deoxywithastramonol...
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