24,25-Dihidroksiholekalciferol

IUPAC ime


(6R)-6-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(5S)-5-hidroksi-2-metilencikloheksiliden]etiliden]-7a-metil-2,3,3a,5,6,7-heksahidro-1H-inden-1-il]-2-metilheptan-2,3-diol

Drugi nazivi

24,25-dihidroksivitamin D₃
(24R)-hidroksikalcifediol
(24R)-hidroksikalcidiol

Identifikacija

CAS registarski broj

40013-87-4^Y

PubChem^[1]^[2]

6434253

ChemSpider^[3]

4939193^Y

ChEMBL^[4]

CHEMBL47183^Y

Jmol-3D slike

Slika 1

SMILES

O[C@@H]1CC(\C(=C)CC1)=C\C=C2/CCC[C@]3([C@H]2CC[C@@H]3[C@H](C)CCC(O)C(O)(C)C)C

InChI

InChI=1S/C27H44O3/c1-18-8-12-22(28)17-21(18)11-10-20-7-6-16-27(5)23(13-14-24(20)27)19(2)9-15-25(29)26(3,4)30/h10-11,19,22-25,28-30H,1,6-9,12-17H2,2-5H3/b20-10+,21-11-/t19-,22+,23-,24+,25?,27-/m1/s1^Y
Kod: FCKJYANJHNLEEP-SRLFHJKTSA-N^Y

InChI=1/C27H44O3/c1-18-8-12-22(28)17-21(18)11-10-20-7-6-16-27(5)23(13-14-24(20)27)19(2)9-15-25(29)26(3,4)30/h10-11,19,22-25,28-30H,1,6-9,12-17H2,2-5H3/b20-10+,21-11-/t19-,22+,23-,24+,25?,27-/m1/s1
Kod: FCKJYANJHNLEEP-SRLFHJKTBM

Svojstva

Molekulska formula

C₂₇H₄₄O₃

Molarna masa

416,63 g/mol

Y (šta je ovo?) (verifikuj)

Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala

Infobox references

24,25-Dihidroksiholekalciferol (24,25-dihidroksivitamin D₃, (24R)-hidroksikalcidiol, 24(R),25-(OH)₂D₃)^[5] je jedinjenje koje je blisko srodno sa 1,25-dihidroksivitamin D₃, aktivnom formom vitamina D₃, ali je poput samog vitamina D₃ i 25-hidroksivitamina D₃ neaktivan kao hormon in vitro^[6] i in vivo.^[7]^[8]

Reference

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit
↑ "Nomenclature of Vitamin D. Recommendations 1981. IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN)" reproduced at the Queen Mary, University of London website. Retrieved 21 March 2010.
↑ Sørnes, S.; Bjøro, T.; Berg, J. P.; Torjesen, P. A.; Haug, E. (1994). „Calcitriol attenuates the basal and vasoactive intestinal peptide-stimulated cAMP production in prolactin-secreting rat pituitary (GH4C1) cells”. Molecular and cellular endocrinology 101 (1–2): 183–188. PMID 9397951.
↑ Mortensen, B. M.; Gautvik, K. M.; Gordeladze, J. O. (1993). „Bone turnover in rats treated with 1,25-dihydroxyvitamin D3, 25-hydroxyvitamin D3 or 24,25-dihydroxyvitamin D3”. Bioscience reports 13 (1): 27–39. PMID 8392394.
↑ Holick, MF; Schnoes, HK; Deluca, HF; Gray, RW; Boyle, IT; Suda, T (1972). „Isolation and identification of 24,25-dihydroxycholecalciferol, a metabolite of vitamin D made in the kidney”. Biochemistry 11 (23): 4251–5. DOI:10.1021/bi00773a009. PMID 4342902.

Literatura

Mata-Granados, J. M.; Luque De Castro, M. D.; Quesada Gomez, J. M. (2008). „Inappropriate serum levels of retinol, α-tocopherol, 25 hydroxyvitamin D3 and 24,25 dihydroxyvitamin D3 levels in healthy Spanish adults: Simultaneous assessment by HPLC”. Clinical Biochemistry 41: 676–680. DOI:10.1016/j.clinbiochem.2008.02.003. PMID 18313404.

Spoljašnje veze

Vitamini (A11)

Rastvorljivi u masnoći

A	α-Karoten • β-Karoten • Retinol^# • Tretinoin
D	D₂ (Ergosterol, Ergokalciferol^#) • D₃ (7-Dehidroholesterol, Previtamin D3, Holekalciferol, 25-hidroksiholekalciferol, Kalcitriol (1,25-dihidroksiholekalciferol), Kalcitronska kiselina) D₄ (Dihidroergokalciferol) • D₅ • D analozi (Alfakalcidol, Dihidrotakisterol, Kalcipotriol, Takalcitol, Parikalcitol)
E	Tokoferol (Alfa, Beta, Gama, Delta) • Tokotrienol (Alfa, Beta, Gama, Delta) • Tokofersolan
K	Naftohinon • Filohinon (K₁) • Menatetrenon (K₂) • Menadion (K₃) • Menadiol (K₄)

Rastvorljivi u vodi

B	B₁ (Tiamin^#) • B₂ (Riboflavin^#) • B₃ (Niacin, Nikotinamid^#) • B₅ (Pantotenska kiselina, Dekspantenol, Pantetin) • B₆ (Piridoksin^#, Piridoksal fosfat, Piridoksamin) B₇ (Biotin) • B₉ (Folna kiselina, Dihidrofolna kiselina, Folinska kiselina, L-metilfolat) • B₁₂ (Cijanokobalamin, Hidroksokobalamin, Metilkobalamin, Kobamamid) • B₁₃ (Orotična kiselina) • B₂₀ (Karnitin) • B_p (Holin)
C	Askorbinska kiselina^# • Dehidroaskorbinska kiselina