24,25-Dihydroxyvitamin D (BioDeep_00000006580)
Secondary id: BioDeep_00000028182, BioDeep_00000173723, BioDeep_00000873022, BioDeep_00001868115
human metabolite Endogenous blood metabolite
代谢物信息卡片
(6R)-6-[(1R,3aS,4E,7aR)-4-{2-[(1Z,5R)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-2-methylheptane-2,3-diol
化学式: C27H44O3 (416.3290274)
中文名称: 24,25-二羟基维生素 D3, 司骨化醇
谱图信息:
最多检出来源 Homo sapiens(blood) 0.39%
分子结构信息
SMILES: C=C1CCC(O)CC1=CC=C1CCCC2(C)C1CCC2C(C)CCC(O)C(C)(C)O
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
描述信息
24,25-Dihydroxyvitamin D (24R,25(OH)2D3) circulates in blood at concentrations about 1000 times higher than 1alpha,25(OH)2D3. 24-Hydroxylase is present in the proximal convoluted tubule cells of the kidney and in virtual all target cells of 1alpha,25(OH)2D3. Interestingly, 1alpha,25(OH)2D3 is a very strong inducer of 24-hydroxylase activity and 24R,25(OH)2D3 formation. Also parathyroid hormone (PTH) regulates 24-hydroxylase activity but in a tissue specific manner, i.e. inhibitory in the kidney while a synergistic effect together with 1alpha,25(OH)2D3 is observed in osteoblasts. Generally, 24-hydroxylation has been considered the first step in the degradation pathway of 1alpha,25(OH)2D3 and 25-(OH)D3. However, through the past decades data have accumulated that 24R,25(OH)2D3 is not merely a degradation product but has effects on its own. Classic studies have demonstrated the significance of 24R,25(OH)2D3 for normal chicken egg hatchability and calcium and phosphorus homeostasis. More recently it became apparent that 24R,25(OH)2D3 also has distinct effects on cartilage in particular the resting zone cells. 24R,25(OH)2D3 stimulates osteocalcin synthesis in human osteoblasts. 24R,25(OH)2D3 plays a role in bone metabolism but that it acts in concert with 1alpha,25(OH)2D3 to obtain an optimal effect. (PMID: 11179746).
D018977 - Micronutrients > D014815 - Vitamins > D004100 - Dihydroxycholecalciferols
D018977 - Micronutrients > D014815 - Vitamins > D006887 - Hydroxycholecalciferols
D000077264 - Calcium-Regulating Hormones and Agents
D050071 - Bone Density Conservation Agents
同义名列表
21 个代谢物同义名
(6R)-6-[(1R,3aS,4E,7aR)-4-{2-[(1Z,5R)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-2-methylheptane-2,3-diol; (3b,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-3,24,25-triol; 24,25-Dihydroxyvitamin D 3, (3beta,5Z,7E,24R)-isomer; (24S)-24,25-Dihydroxyvitamin D3; (24R)-24,25-Dihydroxyvitamin D3; 24R,25-Dihydroxycholecalciferol; 24,25 Dihydroxycholecalciferol; 24,25-Dihydroxycholecalciferol; 24,25 Dihydroxyvitamin D 3; Dihydroxyvitamin D3, 24,25; 24,25-Dihydroxyvitamin D 3; 24,25-Dihydroxy-vitamin D; 24,25-Dihydroxyvitamin D3; 24,25 Dihydroxyvitamin D3; 24,25-Dihydroxyvitamin D; 24,25-hydroxyvitamin D3; 24,25-Dihydroxyvitamin; 24-Hydroxycalcidiol; 24 25-Dihydroxy VD3; Secalciferol; Vitamin D
数据库引用编号
21 个数据库交叉引用编号
- ChEBI: CHEBI:108603
- ChEBI: CHEBI:28818
- ChEBI: CHEBI:89324
- KEGG: C07712
- PubChem: 12895043
- PubChem: 5283748
- PubChem: 1590
- HMDB: HMDB0000430
- Metlin: METLIN220
- ChEMBL: CHEMBL1590076
- MeSH: 24,25-Dihydroxyvitamin D 3
- foodb: FDB112199
- chemspider: 17215953
- CAS: 55721-11-4
- CAS: 40013-87-4
- PMhub: MS000019642
- PubChem: 9914
- LipidMAPS: LMST03020273
- 3DMET: B05256
- NIKKAJI: J458.721I
- RefMet: 24,25-Dihydroxyvitamin D3
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
7 个相关的物种来源信息
- 9606 Homo sapiens:
- 1957 Streptomyces sclerotialus: 10.1128/AEM.57.10.2841-2846.1991
- 67294 Streptomyces filamentosus: 10.1128/AEM.57.10.2841-2846.1991
- 9606 Homo sapiens:
- 1957 Streptomyces sclerotialus: 10.1128/AEM.57.10.2841-2846.1991
- 67294 Streptomyces filamentosus: 10.1128/AEM.57.10.2841-2846.1991
- 9606 Homo sapiens: -
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Anastasia Alexandridou, Dietrich A Volmer. 2-fluoro-1-methylpyridinium p-toluene sulfonate: a new LC-MS/MS derivatization reagent for vitamin D metabolites.
Journal of lipid research.
2023 08; 64(8):100409. doi:
10.1016/j.jlr.2023.100409. [PMID: 37406930] - Simon Hsu, Leila R Zelnick, Yvonne S Lin, Cora M Best, Bryan R Kestenbaum, Kenneth E Thummel, Andrew N Hoofnagle, Ian H de Boer. Validation of the 24,25-dihydroxyvitamin D3 to 25-hydroxyvitamin D3 ratio as a biomarker of 25-hydroxyvitamin D3 clearance.
The Journal of steroid biochemistry and molecular biology.
2022 03; 217(?):106047. doi:
10.1016/j.jsbmb.2021.106047. [PMID: 34954017] - Sieglinde Zelzer, Caroline Le Goff, Stéphanie Peeters, Chiara Calaprice, Andreas Meinitzer, Dietmar Enko, Walter Goessler, Markus Herrmann, Etienne Cavalier. Comparison of two LC-MS/MS methods for the quantification of 24,25-dihydroxyvitamin D3 in patients and external quality assurance samples.
Clinical chemistry and laboratory medicine.
2022 01; 60(1):74-81. doi:
10.1515/cclm-2021-0792. [PMID: 34727586] - Dae-Hyun Ko, Sun-Hee Jun, Youngwon Nam, Sang H Song, Minje Han, Yeo-Min Yun, Kyunghoon Lee, Junghan Song. Multiplex LC-MS/MS for simultaneous determination of 25-hydroxyvitamin D, 24,25-dihydroxyvitamin D3, albumin, and vitamin D-binding protein with its isoforms: One-step estimation of bioavailable vitamin D and vitamin D metabolite ratio.
The Journal of steroid biochemistry and molecular biology.
2021 02; 206(?):105796. doi:
10.1016/j.jsbmb.2020.105796. [PMID: 33259939] - Hyun-Ki Kim, Hye Jin Chung, Hương Giang Lê, Byoung-Kuk Na, Min-Chul Cho. Serum 24,25-dihydroxyvitamin D level in general Korean population and its relationship with other vitamin D biomarkers.
PloS one.
2021; 16(2):e0246541. doi:
10.1371/journal.pone.0246541. [PMID: 33606762] - Alexandra Povaliaeva, Ekaterina Pigarova, Artem Zhukov, Viktor Bogdanov, Larisa Dzeranova, Olga Mel'nikova, Elena Pekareva, Natalya Malysheva, Vitaliy Ioutsi, Larisa Nikankina, Liudmila Rozhinskaya. Evaluation of Vitamin D Metabolism in Patients with Type 1 Diabetes Mellitus in the Setting of Cholecalciferol Treatment.
Nutrients.
2020 Dec; 12(12):. doi:
10.3390/nu12123873. [PMID: 33352890] - Sieglinde Zelzer, Andreas Meinitzer, Dietmar Enko, Sebastian Simstich, Caroline Le Goff, Etienne Cavalier, Markus Herrmann, Walter Goessler. Simultaneous determination of 24,25- and 25,26-dihydroxyvitamin D3 in serum samples with liquid-chromatography mass spectrometry - A useful tool for the assessment of vitamin D metabolism.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2020 Nov; 1158(?):122394. doi:
10.1016/j.jchromb.2020.122394. [PMID: 33091679] - Anna E Goodroe, Casey Fitz, Michael L Power, Ricki J Colman, Saverio Capuano, Toni E Ziegler. Evaluation of vitamin D3 metabolites in Callithrix jacchus (common marmoset).
American journal of primatology.
2020 06; 82(6):e23131. doi:
10.1002/ajp.23131. [PMID: 32270886] - Etienne Cavalier, Loreen Huyghebaert, Olivier Rousselle, Anne-Catherine Bekaert, Stéphanie Kovacs, Laura Vranken, Stéphanie Peeters, Caroline Le Goff, Aurélie Ladang. Simultaneous measurement of 25(OH)-vitamin D and 24,25(OH)2-vitamin D to define cut-offs for CYP24A1 mutation and vitamin D deficiency in a population of 1200 young subjects.
Clinical chemistry and laboratory medicine.
2020 01; 58(2):197-201. doi:
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Medical science monitor : international medical journal of experimental and clinical research.
2019 Dec; 25(?):9159-9166. doi:
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The Journal of clinical endocrinology and metabolism.
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The Journal of steroid biochemistry and molecular biology.
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Nutrients.
2019 Oct; 11(10):. doi:
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Clinical and experimental nephrology.
2019 Oct; 23(10):1202-1210. doi:
10.1007/s10157-019-01760-3. [PMID: 31240503] - Anjali Verma, D Joshua Cohen, Nofrat Schwartz, Chandana Muktipaty, Jennifer E Koblinski, Barbara D Boyan, Zvi Schwartz. 24R,25-Dihydroxyvitamin D3 regulates breast cancer cells in vitro and in vivo.
Biochimica et biophysica acta. General subjects.
2019 10; 1863(10):1498-1512. doi:
10.1016/j.bbagen.2019.05.013. [PMID: 31125679] - Anjali Verma, Zvi Schwartz, Barbara D Boyan. 24R,25-dihydroxyvitamin D3 modulates tumorigenicity in breast cancer in an estrogen receptor-dependent manner.
Steroids.
2019 10; 150(?):108447. doi:
10.1016/j.steroids.2019.108447. [PMID: 31302113] - Glenville Jones, Martin Kaufmann. Update on pharmacologically-relevant vitamin D analogues.
British journal of clinical pharmacology.
2019 06; 85(6):1095-1102. doi:
10.1111/bcp.13781. [PMID: 30308088] - Martin Kaufmann, Corine Martineau, Alice Arabian, Mary Traynor, René St-Arnaud, Glenville Jones. Calcioic acid: In vivo detection and quantification of the terminal C24-oxidation product of 25-hydroxyvitamin D3 and related intermediates in serum of mice treated with 24,25-dihydroxyvitamin D3.
The Journal of steroid biochemistry and molecular biology.
2019 04; 188(?):23-28. doi:
10.1016/j.jsbmb.2018.12.001. [PMID: 30553931] - G D Carter, F Ahmed, J Berry, E Cavalier, R Durazo-Arvizu, E Gunter, G Jones, J Jones, K Phinney, C T Sempos, P J Twomey, E L Williams, S A Wise. External Quality Assessment of 24,25-dihydroxyvitamin D3 (24,25(OH)2D3) assays.
The Journal of steroid biochemistry and molecular biology.
2019 03; 187(?):130-133. doi:
10.1016/j.jsbmb.2018.11.010. [PMID: 30476591] - Danyang Li, Louisa E Jeffery, Carl Jenkinson, Stephanie R Harrison, Rene F Chun, John S Adams, Karim Raza, Martin Hewison. Serum and synovial fluid vitamin D metabolites and rheumatoid arthritis.
The Journal of steroid biochemistry and molecular biology.
2019 03; 187(?):1-8. doi:
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The Journal of steroid biochemistry and molecular biology.
2019 02; 186(?):79-88. doi:
10.1016/j.jsbmb.2018.09.019. [PMID: 30278215] - Qi Dai, Xiangzhu Zhu, JoAnn E Manson, Yiqing Song, Xingnan Li, Adrian A Franke, Rebecca B Costello, Andrea Rosanoff, Hui Nian, Lei Fan, Harvey Murff, Reid M Ness, Douglas L Seidner, Chang Yu, Martha J Shrubsole. Magnesium status and supplementation influence vitamin D status and metabolism: results from a randomized trial.
The American journal of clinical nutrition.
2018 12; 108(6):1249-1258. doi:
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Nutrition research (New York, N.Y.).
2018 11; 59(?):36-43. doi:
10.1016/j.nutres.2018.07.008. [PMID: 30442231] - Albert Shieh, Christina Ma, Rene F Chun, Jonas Wittwer-Schegg, Leon Swinkels, Tonnie Huijs, Jeffrey Wang, Ines Donangelo, Martin Hewison, John S Adams. Associations Between Change in Total and Free 25-Hydroxyvitamin D With 24,25-Dihydroxyvitamin D and Parathyroid Hormone.
The Journal of clinical endocrinology and metabolism.
2018 09; 103(9):3368-3375. doi:
10.1210/jc.2018-00515. [PMID: 29931358] - Michiyasu Ishizawa, Daisuke Akagi, Makoto Makishima. Lithocholic Acid Is a Vitamin D Receptor Ligand That Acts Preferentially in the Ileum.
International journal of molecular sciences.
2018 07; 19(7):. doi:
10.3390/ijms19071975. [PMID: 29986424] - Cora M Best, Eva K Pressman, Ruth Anne Queenan, Elizabeth Cooper, Françoise Vermeylen, Kimberly O O'Brien. Gestational Age and Maternal Serum 25-hydroxyvitamin D Concentration Interact to Affect the 24,25-dihydroxyvitamin D Concentration in Pregnant Adolescents.
The Journal of nutrition.
2018 06; 148(6):868-875. doi:
10.1093/jn/nxy043. [PMID: 29796622] - Anouk M M Vaes, Michael Tieland, Margot F de Regt, Jonas Wittwer, Luc J C van Loon, Lisette C P G M de Groot. Dose-response effects of supplementation with calcifediol on serum 25-hydroxyvitamin D status and its metabolites: A randomized controlled trial in older adults.
Clinical nutrition (Edinburgh, Scotland).
2018 06; 37(3):808-814. doi:
10.1016/j.clnu.2017.03.029. [PMID: 28433267] - Stephanie A Bora, Mary J Kennett, Philip B Smith, Andrew D Patterson, Margherita T Cantorna. Regulation of vitamin D metabolism following disruption of the microbiota using broad spectrum antibiotics.
The Journal of nutritional biochemistry.
2018 06; 56(?):65-73. doi:
10.1016/j.jnutbio.2018.01.011. [PMID: 29459310] - Laura A Graeff-Armas, Martin Kaufmann, Elizabeth Lyden, Glenville Jones. Serum 24,25-dihydroxyvitamin D3 response to native vitamin D2 and D3 Supplementation in patients with chronic kidney disease on hemodialysis.
Clinical nutrition (Edinburgh, Scotland).
2018 06; 37(3):1041-1045. doi:
10.1016/j.clnu.2017.04.020. [PMID: 28506446] - Hemamalini Ketha, Tom D Thacher, Sara S Oberhelman, Philip R Fischer, Ravinder J Singh, Rajiv Kumar. Comparison of the effect of daily versus bolus dose maternal vitamin D3 supplementation on the 24,25-dihydroxyvitamin D3 to 25-hydroxyvitamin D3 ratio.
Bone.
2018 05; 110(?):321-325. doi:
10.1016/j.bone.2018.02.024. [PMID: 29486367] - Robin Taylor Wilson, Loren D Masters, Jill S Barnholtz-Sloan, Anna C Salzberg, Terryl J Hartman. Ancestry-Adjusted Vitamin D Metabolite Concentrations in Association With Cytochrome P450 3A Polymorphisms.
American journal of epidemiology.
2018 04; 187(4):754-766. doi:
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Bone.
2018 02; 107(?):124-130. doi:
10.1016/j.bone.2017.11.011. [PMID: 29155243] - Stephanie A Bora, Mary J Kennett, Philip B Smith, Andrew D Patterson, Margherita T Cantorna. The Gut Microbiota Regulates Endocrine Vitamin D Metabolism through Fibroblast Growth Factor 23.
Frontiers in immunology.
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Clinica chimica acta; international journal of clinical chemistry.
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Clinical journal of the American Society of Nephrology : CJASN.
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Journal of AOAC International.
2017 Sep; 100(5):1308-1317. doi:
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The Journal of nutritional biochemistry.
2017 08; 46(?):21-29. doi:
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Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research.
2017 Jul; 32(7):1589-1596. doi:
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Journal of chromatography. A.
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Clinical endocrinology.
2017 May; 86(5):674-679. doi:
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Medicine and science in sports and exercise.
2017 02; 49(2):349-356. doi:
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Analytical and bioanalytical chemistry.
2016 Nov; 408(27):7617-7627. doi:
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Journal of molecular endocrinology.
2016 08; 57(2):87-96. doi:
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Clinical journal of the American Society of Nephrology : CJASN.
2016 07; 11(7):1145-53. doi:
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American journal of kidney diseases : the official journal of the National Kidney Foundation.
2016 May; 67(5):812-3. doi:
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Clinical nutrition (Edinburgh, Scotland).
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Journal of pediatric gastroenterology and nutrition.
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Annals of nutrition & metabolism.
2016; 68(2):119-27. doi:
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PloS one.
2016; 11(12):e0167848. doi:
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American journal of nephrology.
2016; 44(4):316-325. doi:
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World journal of gastroenterology.
2015 Oct; 21(39):11152-9. doi:
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The Journal of clinical endocrinology and metabolism.
2015 Oct; 100(10):E1343-52. doi:
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Analytical chemistry.
2015 Aug; 87(15):7964-70. doi:
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Clinical chemistry.
2015 Jun; 61(6):877-84. doi:
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Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA.
2015 May; 26(5):1655-60. doi:
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Clinical chemistry.
2015 Apr; 61(4):636-45. doi:
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Rinsho byori. The Japanese journal of clinical pathology.
2015 Apr; 63(4):457-64. doi:
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The Journal of steroid biochemistry and molecular biology.
2015 Apr; 148(?):283-9. doi:
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Clinical journal of the American Society of Nephrology : CJASN.
2014 Nov; 9(11):1965-73. doi:
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The Journal of clinical endocrinology and metabolism.
2014 Oct; 99(10):E1830-7. doi:
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The Journal of clinical endocrinology and metabolism.
2014 Sep; 99(9):3373-81. doi:
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American journal of kidney diseases : the official journal of the National Kidney Foundation.
2014 Aug; 64(2):168-70. doi:
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American journal of kidney diseases : the official journal of the National Kidney Foundation.
2014 Aug; 64(2):187-97. doi:
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The Journal of clinical endocrinology and metabolism.
2014 Jul; 99(7):2567-74. doi:
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The American journal of clinical nutrition.
2014 Jun; 99(6):1414-23. doi:
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The Journal of nutrition.
2014 May; 144(5):638-46. doi:
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The Journal of clinical endocrinology and metabolism.
2013 Dec; 98(12):4890-8. doi:
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Clinical endocrinology.
2013 Oct; 79(4):491-8. doi:
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Diabetes care.
2013 Aug; 36(8):2423-9. doi:
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The Journal of clinical endocrinology and metabolism.
2013 Jul; 98(7):2709-15. doi:
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Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research.
2013 Jun; 28(6):1301-7. doi:
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The Journal of clinical endocrinology and metabolism.
2013 Mar; 98(3):1207-13. doi:
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PloS one.
2013; 8(5):e64348. doi:
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Current eye research.
2012 Oct; 37(10):871-8. doi:
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International urology and nephrology.
2012 Aug; 44(4):1135-44. doi:
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The Journal of clinical endocrinology and metabolism.
2012 Apr; 97(4):1243-9. doi:
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The Journal of clinical endocrinology and metabolism.
2012 Mar; 97(3):E423-7. doi:
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Analytical biochemistry.
2011 Nov; 418(1):126-33. doi:
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The Journal of steroid biochemistry and molecular biology.
2011 Sep; 126(3-5):72-7. doi:
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Best practice & research. Clinical endocrinology & metabolism.
2011 Aug; 25(4):531-41. doi:
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Journal of dental research.
2011 Aug; 90(8):1007-12. doi:
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Clinical nutrition (Edinburgh, Scotland).
2011 Apr; 30(2):194-201. doi:
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The Journal of steroid biochemistry and molecular biology.
2010 Feb; 118(3):188-93. doi:
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The Journal of steroid biochemistry and molecular biology.
2010 Feb; 118(3):162-70. doi:
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Journal of neuroimmunology.
2009 Aug; 213(1-2):135-41. doi:
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Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research.
2008 Sep; 23(9):1486-96. doi:
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The American journal of clinical nutrition.
2008 Aug; 88(2):491S-499S. doi:
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Clinical biochemistry.
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The American journal of the medical sciences.
2008 Apr; 335(4):278-83. doi:
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2007 Dec; 22 Suppl 2(?):V11-5. doi:
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General and comparative endocrinology.
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Steroids.
2007 Feb; 72(2):158-64. doi:
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The Israel Medical Association journal : IMAJ.
2007 Jan; 9(1):35-8. doi:
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Journal of cellular biochemistry.
2006 May; 98(2):309-34. doi:
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Journal of cellular biochemistry.
2005 Sep; 96(1):97-108. doi:
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Voprosy pitaniia.
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The Journal of steroid biochemistry and molecular biology.
2004 Nov; 92(4):317-25. doi:
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Journal of pharmaceutical and biomedical analysis.
2004 May; 35(3):575-82. doi:
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