7-Dehydrodesmosterol (BioDeep_00000005715)

 

Secondary id: BioDeep_00001868773

human metabolite Endogenous


Metabolite Card


(1S,2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol

Formula: C27H42O (382.3235482)
Chinese Names:
Spectrum Hits: Top Source Viridiplantae(plant) 2.67%

Molecular Structure

SMILES: C/C(C)=CCC[C@H]([C@@]1([H])CC[C@@]2([H])C([C@]3([H])CC[C@]12C)=CC=C4C[C@@H](O)CC[C@@]43C)C
InChI: InChI=1S/C27H42O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,9-10,19,21,23-25,28H,6,8,11-17H2,1-5H3/t19-,21+,23-,24+,25+,26+,27-/m1/s1

Description

7-dehydrodesmosterol, also known as cholesta-5,7,24-trien-3beta-ol or 24-dehydroprovitamin d3, belongs to cholesterols and derivatives class of compounds. Those are compounds containing a 3-hydroxylated cholestane core. Thus, 7-dehydrodesmosterol is considered to be a sterol lipid molecule. 7-dehydrodesmosterol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). 7-dehydrodesmosterol can be found in a number of food items such as nectarine, orange bell pepper, cinnamon, and carrot, which makes 7-dehydrodesmosterol a potential biomarker for the consumption of these food products. In humans, 7-dehydrodesmosterol is involved in several metabolic pathways, some of which include atorvastatin action pathway, simvastatin action pathway, pamidronate action pathway, and steroid biosynthesis. 7-dehydrodesmosterol is also involved in several metabolic disorders, some of which include mevalonic aciduria, wolman disease, chondrodysplasia punctata II, X linked dominant (CDPX2), and hyper-igd syndrome.
7-Dehydrodesmosterol is a sterol intermediate in the biosynthesis of steroids. 7-Dehydrodesmosterol is a substrate of the enzyme 24-dehydrocholesterol reductase (EC:1.3.1.72), an important enzyme in the biosynthesis of Cholesterol. Cholesterol is synthesized from either Lathosterol, 7-Dehydrocholesterol, Desmosterol or Cholestenol by the enzyme 3beta-hydroxysterol delta7 reductase (EC 1.3.1.21, Dhcr7). The Smith-Lemli-Opitz syndrome (SLOS, OMIM 270400) is caused by a genetic defect in cholesterol biosynthesis; mutations in the enzyme 3beta-hydroxysterol delta7 reductase lead to a failure of cholesterol synthesis, with an accumulation of precursor sterols, such as 7-Dehydrodesmosterol. SLOS results in craniofacial, limb as well as major organ defects, including the brain. In individuals with this syndrome, mental retardation, as well as other CNS dysfunction, is almost 100\\% prevalent. (PMID: 15862627, 17197219).

Synonyms

13 synonym names

(1S,2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol; Cholesta-5,7,24-trien-3 beta-ol; cholest-5Z,7Z,24-trien-3beta-ol; Cholesta-5,7,24-triene-3beta-ol; Cholesta-5,7,24-trien-3beta-ol; Cholesta-5,7,24-triene-3β-ol; Cholesta-5,7,24-triene-3b-ol; Cholesta-5,7,24-trien-3b-ol; Cholesta-5,7,24-trien-3β-ol; 7,8-Didehydrodesmosterol; 24-Dehydroprovitamin D3; 7-Dehydrodesmosterol; SCHEMBL12740951



Cross Reference

17 cross reference id

Classification Terms

Related Pathways

Reactome(4)

BioCyc(4)

PlantCyc(0)

Biological Process

267 related biological process reactions.

Reactome(75)

BioCyc(7)

WikiPathways(3)

Plant Reactome(3)

INOH(0)

PlantCyc(125)

COVID-19 Disease Map(0)

PathBank(54)

PharmGKB(0)

7 organism taxonomy source information

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。

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Literature Reference

  • Hongwei Yu, Bassam Wakim, Man Li, Brian Halligan, G Stephen Tint, Shailendra B Patel. Quantifying raft proteins in neonatal mouse brain by 'tube-gel' protein digestion label-free shotgun proteomics. Proteome science. 2007 Sep; 5(?):17. doi: 10.1186/1477-5956-5-17. [PMID: 17892558]
  • S A Holick, M S Lezin, D Young, S Malaikal, M F Holick. Isolation and identification of 24-dehydroprovitamin D3 and its photolysis to 24-dehydroprevitamin D3 in mammalian skin. The Journal of biological chemistry. 1985 Oct; 260(22):12181-4. doi: . [PMID: 2995363]