| Record Information |
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| Version | 1.0 |
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| Creation date | 2011-09-21 00:35:41 UTC |
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| Update date | 2015-07-21 06:57:54 UTC |
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| Primary ID | FDB023846 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | 24R,25-Dihydroxyvitamin D3 |
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| Description | 24R,25-Dihydroxyvitamin D3 (24(R),25(OH)2D3 ) is a vitamin D metabolite, a dihydroxylated form of the seco-steroid. With the identification of a target cell, the growth plate resting zone (RC) chondrocyte, studies indicate that there are specific membrane-associated signal transduction pathways that mediate both rapid, nongenomic and genomic responses of RC cells to 24(R),25(OH)2D3. These studies indicate that 24(R),25(OH)2D3 plays an important role in endochondral ossification by regulating less mature chondrocytes and promoting their maturation in the endochondral lineage.
24(R),25(OH)2D3 binds RC chondrocyte membranes with high specificity, resulting in an increase in protein kinase C (PKC) activity. The effect is stereospecific; 24R,25(OH)2D3, but not 24S,25-(OH)2D3, causes the increase, indicating a receptor-mediated response. Phospholipase D-2 (PLD2) activity is increased, resulting in increased production of diacylglycerol (DAG), which in turn activates PKC. 24(R),25(OH)2D3 does not cause translocation of PKC to the plasma membrane, but activates existing PKCα. There is a rapid decrease in Ca2+ efflux, and influx is stimulated. 24(R),25(OH)2D3 also reduces arachidonic acid release by decreasing phospholipase A2 (PLA2) activity, thereby decreasing available substrate for prostaglandin production via the action of cyclooxygenase-1. PGE2 that is produced acts on the EP1 and EP2 receptors expressed by RC cells to downregulate PKC via protein kinase A, but the reduction in PGE2 decreases this negative feedback mechanism. Both pathways converge on MAP kinase, leading to new gene expression. One consequence of this is production of new matrix vesicles containing PKCα and PKCζ and an increase in PKC activity. The chondrocytes also produce 24(R),25(OH)2D3, and the secreted metabolite acts directly on the matrix vesicle membrane. Only PKCζ is directly affected by 24(R),25(OH)2D3 in the matrix vesicles, and activity of this isoform is inhibited. This effect may be involved in the control of matrix maturation and turnover. 24(R),25(OH)2D3 causes RC cells to mature along the endochondral developmental pathway, where they become responsive to 1α,25(OH)2D3 and lose responsiveness to 24(R),25(OH)2D3, a characteristic of more mature growth zone (GC) chondrocytes. 1α,25(OH)2D3 elicits its effects on GC through different signal transduction pathways than those used by 24(R),25(OH)2D3. (PMID: 11179745) [HMDB] |
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| CAS Number | 55721-11-4 |
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| Structure | |
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| Synonyms | |
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| Predicted Properties | |
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| Chemical Formula | C27H44O3 |
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| IUPAC name | (3R,6R)-6-[(1R,4E,7aR)-4-{2-[(1Z,5S)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-2-methylheptane-2,3-diol |
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| InChI Identifier | 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 |
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| InChI Key | FCKJYANJHNLEEP-AOWQBJNISA-N |
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| Isomeric SMILES | C[C@H](CC[C@@H](O)C(O)(C)C)[C@H]1CCC2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C |
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| Average Molecular Weight | 416.6365 |
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| Monoisotopic Molecular Weight | 416.329045274 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Steroids and steroid derivatives |
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| Sub Class | Vitamin D and derivatives |
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| Direct Parent | Vitamin D and derivatives |
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| Alternative Parents | |
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| Substituents | - Triterpenoid
- Tertiary alcohol
- Cyclic alcohol
- Secondary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Disposition | Route of exposure: Biological location: Source: |
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| Process | Naturally occurring process: |
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| Role | Biological role: Industrial application: |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | |
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| Spectra |
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| Spectra | |
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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| Predicted GC-MS | 24R,25-Dihydroxyvitamin D3, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0a4i-7029200000-c84dd427774a8bd55bf4 | Spectrum | | Predicted GC-MS | 24R,25-Dihydroxyvitamin D3, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-014i-1312049000-f6115b14a152464f5e1b | Spectrum |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00l2-0119200000-7bcd78fea8093a8230ae | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a5a-2369100000-04f3fb5d7d655a9ce470 | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0zgi-4389100000-269c6b355710e7dcd9b8 | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0004900000-7bbe3ea5eae60b2a2059 | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-05mk-0009300000-4137913e2e1e7271894c | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0079-9006000000-b2d6915fde38c349870a | 2017-09-01 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | 29272143 |
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| ChEMBL ID | Not Available |
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| KEGG Compound ID | Not Available |
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| Pubchem Compound ID | 53477805 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | Not Available |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB06226 |
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| CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | Not Available |
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| BIGG ID | 2289319 |
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| KNApSAcK ID | Not Available |
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| HET ID | Not Available |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Not Available |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | Not Available |
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| Enzymes | Not Available |
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| Pathways | Not Available |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | Not Available |
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| Files |
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| MSDS | show |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| Content Reference | |
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