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Vitamin D

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IdImageCOMMON NAMENAMEDATA No Lipid classINFORMANTSYMBOLFORMULAMOL.WT(average)Download cdx file / Mol format file BIOOGICAL ACTIVITY PHYSICAL AND CHEMICAL PROPERTIES SPECTRAL DATA CHROMATOGRAM DATA SOURCE CHEMICAL SYNTHESIS METABOLISM GENETIC INFORMATION NOTE REFERENCES
MELTING POINTBOILING POINTDENSITYREFRACTIVE INDEXOPTICAL ROTATIONSOLUBILITY UV SPECTRAIR SPECTRANMR SPECTRAMASS SPECTRAOTHER SPECTRA
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2b-methoxy-1a,25-dihydroxyvitamin D3 (5Z,7E)-(1R,2R,3R)-2-methoxy-9,10-seco-5,7,10(19)-cholestatriene-1,3,25-triol VVD0706Vitamin DSachiko Yamada C28H46O4 446.662Download ChemDraw structure data(% of 1,25-(OH)2D3 effect) Affinity for chicken intestine vitamin D receptor: 9; Affinity for sheep serum vitamin D binding protein: 3500; Inhibition of proliferation of C3H10T(BMP-4) cells: 11 (FCS-free), 1.5 (10% FCS); CAT assay (osteocalcin): 70; Inhibition of adipogenesis: 0.08. << Ref. 0374>> From C(22) steroid precursor via photochemical method. The C(2) substituent was introduced by nucleophilic opening of 1a,2a-epoxide. << Ref. 0374>> << Ref.0374 >> AUTHOR: Scheddin, D., Mayer, H., Schonecker, B., Gliesing, S., and Reichenbacher, M. TITLE: Synthesis and biological activities of 2 beta-chloro-, 2 beta-fluoro-, and 2 beta-methoxy-1 alpha,25-dihydroxyvitamin D3 PubMed ID:9870260 JOURNAL: Steroids. VOLUME: 63 PAGE: 633-643(1998)
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2b-fluoro-1a,25-dihydroxyvitamin D3 (5Z,7E)-(1R,2R,3R)-2-fluoro-9,10-seco-5,7,10(19)-cholestatriene-1,3,25-triol VVD0705Vitamin DSachiko Yamada C27H43FO3 434.627Download ChemDraw structure data(% of 1,25-(OH)2D3 effect) Affinity for chicken intestine vitamin D receptor: 667; Affinity for sheep serum vitamin D binding protein: 160; Inhibition of proliferation of C3H10T(BMP-4) cells: 133 (FCS-free), 900 (10% FCS); CAT assay (osteocalcin): 130; Inhibition of adipogenesis: 500. << Ref. 0374>> From C(22) steroid precursor via photochemical method. The C(2) substituent was introduced by nucleophilic opening of 1a,2a-epoxide. << Ref. 0374>> << Ref.0374 >> AUTHOR: Scheddin, D., Mayer, H., Schonecker, B., Gliesing, S., and Reichenbacher, M. TITLE: Synthesis and biological activities of 2 beta-chloro-, 2 beta-fluoro-, and 2 beta-methoxy-1 alpha,25-dihydroxyvitamin D3 PubMed ID:9870260 JOURNAL: Steroids. VOLUME: 63 PAGE: 633-643(1998)
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2b-chloro-1a,25-dihydroxyvitamin D3 (5Z,7E)-(1R,2R,3R)-2-chloro-9,10-seco-5,7,10(19)-cholestatriene-1,3,25-triol VVD0704Vitamin DSachiko Yamada C27H43ClO3 451.081Download ChemDraw structure data(% of 1,25-(OH)2D3 effect) Affinity for chicken intestine vitamin D receptor: 100; Affinity for sheep serum vitamin D binding protein: 140; Inhibition of proliferation of C3H10T(BMP-4) cells: 0.9 (FCS-free), 11 (10% FCS); CAT assay (osteocalcin): 130; Inhibition of adipogenesis: 8. << Ref. 0374>> From C(22) steroid precursor via photochemical method. The C(2) substituent was introduced by nucleophilic opening of 1a,2a-epoxide. << Ref. 0374>> << Ref.0374 >> AUTHOR: Scheddin, D., Mayer, H., Schonecker, B., Gliesing, S., and Reichenbacher, M. TITLE: Synthesis and biological activities of 2 beta-chloro-, 2 beta-fluoro-, and 2 beta-methoxy-1 alpha,25-dihydroxyvitamin D3 PubMed ID:9870260 JOURNAL: Steroids. VOLUME: 63 PAGE: 633-643(1998)
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(23R)-1a-hydroxy-25,27-didehydrovitamin D3 26,23-lactone (5Z,7E)-(1S,3R,23R)-1,3-dihydroxy-9,10-seco-5,7,10(19),25(27)-cholestatetraeno-26,23-lactone VVD0703Vitamin DSachiko Yamada 0.000Download ChemDraw structure dataActivity relative to 1,25-(OH)2D3 (defined 1): Affinity for chick intestinal receptor, 1/3.8; Affinity for bovine serum vitamin D binding protein, 1/39.4; HL-60 cell differentiation, no effect; Antagonistic activity, yes. << Ref. 0373>> Convergent synthesis from CD-ring plus side chain fragment and enyne A-ring precursor via palladium catalyzed coupling of the upper and the lower half fragments as a key step. << Ref. 0373>> << Ref.0373 >> AUTHOR: Manabe, K.; Ishizuka, S.; Tanaka, H.; Gao, Q.; Furuya, M.; Tomimori, K.; Sakuma, Y.; and Hazato, A. (1997) Synthesis and Biological Activity of Novel Vitamin D3-Lactone Analogues. In Vitamin D Chemistry, Biology and Clinical Applications of the Steroid Hormone. (Norman, A. W.; Bouillon, R.; Thomasset, M.; eds), pp79-80, Printing and Reprographics University of California, Riverside TITLE: JOURNAL: VOLUME: PAGE: - (1997)
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(23S)-1a-hydroxy-25,27-didehydrovitamin D3 26,23-lactone (5Z,7E)-(1S,3R,23S)-1,3-dihydroxy-9,10-seco-5,7,10(19),25(27)-cholestatetraeno-26,23-lactone VVD0702Vitamin DSachiko Yamada C27H38O4 426.588Download ChemDraw structure dataActivity relative to 1,25-(OH)2D3 (defined 1): Affinity for chick intestinal receptor, 1/9.8; Affinity for bovine serum vitamin D binding protein, 1/10.7; HL-60 cell differentiation, no effect; Antagonistic activity, yes. << Ref. 0373>> Convergent synthesis from CD-ring plus side chain fragment and enyne A-ring precursor via palladium catalyzed coupling of the upper and the lower half fragments as a key step. << Ref. 0373>> << Ref.0373 >> AUTHOR: Manabe, K.; Ishizuka, S.; Tanaka, H.; Gao, Q.; Furuya, M.; Tomimori, K.; Sakuma, Y.; and Hazato, A. (1997) Synthesis and Biological Activity of Novel Vitamin D3-Lactone Analogues. In Vitamin D Chemistry, Biology and Clinical Applications of the Steroid Hormone. (Norman, A. W.; Bouillon, R.; Thomasset, M.; eds), pp79-80, Printing and Reprographics University of California, Riverside TITLE: JOURNAL: VOLUME: PAGE: - (1997)
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(10R)-1a,19,25-trihydroxy-10,19-dihydrovitamin D3 / (10R)-1a,19,25-trihydroxy-10,19-dihydrocholecalciferol (5Z,7E)-(1S,3R,10R)-9,10-seco-5,7-cholestadiene-1,3,19,25-tetrol VVD0701Vitamin DSachiko Yamada C27H46O4 434.652Download ChemDraw structure data (EtOH)lmax (nm) 243, 251, 261 << Ref. 0355>> 1H-NMR(d,CDCl3) 0.543(3H, s, 18-H3), 0.940(3H, d, J = 6.4 Hz, 21-H3), 1.215(6H, s, 26- and 27-H3), 2.23(1H,-t, J = 12 Hz, 4b-H), 2.51(1H, dd, J = 12.6, 4.1 Hz, 4a-H), 2.81(1H, br d, J = 13 Hz, 9b-H), 3.13(1H, m, W/2 = 18 Hz, 10a-H), 3.68(2H, m, 19-H2), 4.04(1H, m, W/2 = 26 Hz, 3aH ), 4.20(1H, m, W/2 = 11 Hz, 1b-H), 5.86 and 6.52(1H and 1H, each d, J = 11.2 Hz, 7- and 6-H) << Ref. 0355>> m/z 434 (M+,35), 416(29), 398(14), 383(7), 305(17), 287(16), 245(37), 81(100) << Ref. 0355>> Hydroboration of 1,25-(OH)2D3 followed by oxidation gave a mixture of epimers at C(10). The C(10) epimers were separated by flash column chromatography. << Ref. 0355>> << Ref.0355 >> AUTHOR: Sicinski, R. R., Prahl, J. M., Smith, C. M., and DeLuca, H. F. TITLE: New 1alpha,25-dihydroxy-19-norvitamin D3 compounds of high biological activity: synthesis and biological evaluation of 2-hydroxymethyl, 2-methyl, and 2-methylene analogues PubMed ID:9804706 JOURNAL: J Med Chem. VOLUME: 41 PAGE: 4662-4674(1998)
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(10S)-1a,19,25-trihydroxy-10,19-dihydrovitamin D3 / (10S)-1a,19,25-trihydroxy-10,19-dihydrocholecalciferol (5Z,7E)-(1S,3R,10S)-9,10-seco-5,7-cholestadiene-1,3,19,25-tetrol VVD0700Vitamin DSachiko Yamada C27H46O4 434.652Download ChemDraw structure data (EtOH)lmax (nm) 243, 251.5, 261 << Ref. 0355>> 1H-NMR(d,CDCl3) 0.544(3H, s, 18-H3), 0.943(3H, d, J = 6.5 Hz, 21-H3), 1.219(6H, s, 26- and 27-H3), 2.14(1H, br d, J = 14 Hz, 4b-H), 2.47(1H, br d, J = 14 Hz, 4a-H), 2.80(2H, br d, J = 12.7 Hz, 9b-H), 3.52(1H, m, W/2 = 17 Hz, 10b-H), 3.64(1H, dd, J = 10.4, 5.4 Hz, one of 19-H2), 4.18(2H, br m, 3aH and one of 19-H2), 4.29(1H, -dt, J = 12.2, 4.3 Hz, 1b-H), 5.96 and 6.33(1H and 1H, each d, J = 11.2 Hz, 7- and 6-H), 5.89 and 6.37(1H and 1H, each d, J = 11.3 Hz, 7- and 6-H) << Ref. 0355>> m/z 434 (M+,36), 416(38), 398(21), 383(9), 305(14), 287(18), 245(33), 81(100) << Ref. 0355>> Hydroboration of 1,25-(OH)2D3 followed by oxidation gave a mixture of epimers at C(10). The C(10) epimers were separated by flash column chromatography. << Ref. 0355>> << Ref.0355 >> AUTHOR: Sicinski, R. R., Prahl, J. M., Smith, C. M., and DeLuca, H. F. TITLE: New 1alpha,25-dihydroxy-19-norvitamin D3 compounds of high biological activity: synthesis and biological evaluation of 2-hydroxymethyl, 2-methyl, and 2-methylene analogues PubMed ID:9804706 JOURNAL: J Med Chem. VOLUME: 41 PAGE: 4662-4674(1998)
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(24S)-1a,24-dihydroxyvitamin D2 / (24S)-1a,24-dihydroxyergocalciferol (5Z,7E,22E)-(1S,3R,24S)-9,10-seco-5,7,10(19),22-ergostatetraene-1,3,24-triol VVD0699Vitamin DSachiko Yamada C28H44O3 428.647Download ChemDraw structure data
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(24aE)-1a,25-dihydroxy-24a,24b-didehydro-24a,24b-dihomovitamin D3 /(24aE)-1a,25-dihydroxy-24a,24b-didehydro-24a,24b-dihomocholecalciferol (5Z,7E,24aE)-(1S,3R)-24a,24b-dihomo-9,10-seco-5,7,10(19),24a-cholestatetraene-1,3,25-triol VVD0698Vitamin DSachiko Yamada C29H46O3 442.674Download ChemDraw structure data
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(24E)-1a,25-dihydroxy-24,24a-didehydro-24a,24b-dihomovitamin D3 /(24E)-1a,25-dihydroxy-24,24a-didehydro-24a,24b-dihomocholecalciferol (5Z,7E,24E)-(1S,3R)-24a,24b-dihomo-9,10-seco-5,7,10(19),24-cholestatetraene-1,3,25-triol VVD0697Vitamin DSachiko Yamada C29H46O3 442.674Download ChemDraw structure data
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1a-hydroxy-18-(5-hydroxy-5-methyl-3-hexynyloxy)-23,24,25,26,27-pentanorvitamin D3 / 1a-hydroxy-18-(5-hydroxy-5-methyl-3-hexynyloxy)-23,24,25,26,27-pentanorcholecalciferol (5Z,7E)-(1S,3R)-18-(5-hydroxy-5-methyl-3-hexynyloxy)-23,24-dinor-9,10-seco-5,7,10(19)-cholatriene-1,3-diol VVD0696Vitamin DSachiko Yamada C29H44O4 456.657Download ChemDraw structure data
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1a-hydroxy-18-(5-hydroxy-5-methyl-2-hexynyloxy)-23,24,25,26,27-pentanorvitamin D3 / 1a-hydroxy-18-(5-hydroxy-5-methyl-2-hexynyloxy)-23,24,25,26,27-pentanorcholecalciferol (5Z,7E)-(1S,3R)-18-(5-hydroxy-5-methyl-2-hexynyloxy)-23,24-dinor-9,10-seco-5,7,10(19)-cholatriene-1,3-diol VVD0695Vitamin DSachiko Yamada C29H44O4 456.657Download ChemDraw structure data
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1a-hydroxy-18-(4-hydroxy-4-ethyl-2-hexynyloxy)-23,24,25,26,27-pentanorvitamin D3 / 1a-hydroxy-18-(4-hydroxy-4-ethyl-2-hexynyloxy)-23,24,25,26,27-pentanorcholecalciferol (5Z,7E)-(1S,3R)-18-(4-hydroxy-4-ethyl-2-hexynyloxy)-23,24-dinor-9,10-seco-5,7,10(19)-cholatriene-1,3-diol VVD0694Vitamin DSachiko Yamada C30H46O4 470.684Download ChemDraw structure data
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1a-hydroxy-18-(4-hydroxy-4-methyl-2-pentynyloxy)-23,24,25,26,27-pentanorvitamin D3 / 1a-hydroxy-18-(4-hydroxy-4-methyl-2-pentynyloxy)-23,24,25,26,27-pentanorcholecalciferol (5Z,7E)-(1S,3R)-18-(4-hydroxy-4-methyl-2-pentynyloxy)-23,24-dinor-9,10-seco-5,7,10(19)-cholatriene-1,3-diol VVD0693Vitamin DSachiko Yamada C28H42O4 442.631Download ChemDraw structure data
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1a-hydroxy-18-[m-(1-hydroxy-1-ethylpropyl)-benzyloxy]-23,24,25,26,27-pentanorvitamin D3 / 1a-hydroxy-18-[m-(1-hydroxy-1-ethylpropyl)-benzyloxy]-23,24,25,26,27-pentanorcholecalciferol (5Z,7E)-(1S,3R)-18-[m-(1-hydroxy-1-ethylpropyl)-benzyloxy]-23,24-dinor-9,10-seco-5,7,10(19)-cholatriene-1,3-diol VVD0692Vitamin DSachiko Yamada C34H50O4 522.758Download ChemDraw structure data
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1a-hydroxy-18-[m-(1-hydroxy-1-methylethyl)-benzyloxy]-23,24,25,26,27-pentanorvitamin D3 / 1a-hydroxy-18-[m-(1-hydroxy-1-methylethyl)-benzyloxy]-23,24,25,26,27-pentanorcholecalciferol (5Z,7E)-(1S,3R)-18-[m-(1-hydroxy-1-methylethyl)-benzyloxy]-23,24-dinor-9,10-seco-5,7,10(19)-cholatriene-1,3-diol VVD0691Vitamin DSachiko Yamada C32H46O4 494.705Download ChemDraw structure data
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1a-hydroxy-18-(5-hydroxy-5-methylhexyloxy)-23,24,25,26,27-pentanorvitamin D3 / 1a-hydroxy-18-(5-hydroxy-5-methylhexyloxy)-23,24,25,26,27-pentanorcholecalciferol (5Z,7E)-(1S,3R)-18-(5-hydroxy-5-methylhexyloxy)-23,24-dinor-9,10-seco-5,7,10(19)-cholatriene-1,3-diol VVD0690Vitamin DSachiko Yamada C29H48O4 460.689Download ChemDraw structure data
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1a-hydroxy-18-(4-hydroxy-4-ethylhexyloxy)-23,24,25,26,27-pentanorvitamin D3 / 1a-hydroxy-18-(4-hydroxy-4-ethylhexyloxy)-23,24,25,26,27-pentanorcholecalciferol (5Z,7E)-(1S,3R)-18-(4-hydroxy-4-ethylhexyloxy)-23,24-dinor-9,10-seco-5,7,10(19)-cholatriene-1,3-diol VVD0689Vitamin DSachiko Yamada C30H50O4 474.716Download ChemDraw structure data