3β-hydroxy-7,12-diketo-5β-cholan-24-oic acid | 3615-35-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3β-hydroxy-7,12-diketo-5β-cholan-24-oic acid
• 英文别名: 3β-hydroxy-7,12-dioxo-5β-cholan-24-oic acid；3β-hydroxy-7,12-dioxo-5α-cholan-24-oic acid；3β-Hydroxy-7,12-dioxo-5α-cholan-24-saeure；3β-Hydroxy-7,12-dioxo-5β-cholansaeure-(24)；3beta-Hydroxy-7,12-dioxo-5beta-cholan-24-oic Acid；(4R)-4-[(3S,5S,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-7,12-dioxo-2,3,4,5,6,8,9,11,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 3615-35-8
• 化学式: C₂₄H₃₆O₅
• 分子量: 404.547
• InChiKey: MAFJMPFLJJCSTB-WZEKGQGHSA-N

物化性质

• 熔点：
  257-258 °C
• 沸点：
  582.2±50.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲醇 、 3β-hydroxy-7,12-diketo-5β-cholan-24-oic acid 在 甲烷磺酸 、 sodium sulfate 作用下， 反应 0.03h， 生成 methyl 3β-hydroxy-7,12-dioxo-5β-cholanate
  参考文献：
  名称：

  脱氢胆酸的区域和立体选择性还原

  摘要：

  脱氢胆酸 (DHCA) 是一种非天然胆汁酸，由胆酸氧化制成。据报道，它通过两种担子菌（Trametes hirsuta 和 Collybia velutipes）进行生物转化。这些菌丝体对底物和攻击选择性表现出不同的亲和力：T. hirsuta 特别是区域选择性和立体选择性还原 3-keto 基团以产生 3 alpha-hydroxy-7,12-diketo-5 beta-cholan-24-oic acid (7,12-diketolithocolic acid) 为主要产品。对 DHCA 进行了许多不同的化学还原；其中，在高强度超声下与雷尼镍在水中的氢化证明具有高度的区域和立体选择性，仅产生 7,12-二酮基乙醇酸。由于一系列 1D 和 2D NMR 运行，包括 DEPT、NOESY、HH COSY、gHSQC 和 gHMBC，详细指定了 (1)H 和 (13)C 共振。

  DOI：

  10.1016/j.steroids.2006.01.004
• 作为产物：
  描述：

  去氢胆酸 在 potassium phosphate 、 聚合甲醛 、 1,4-二巯基-2,3-丁二醇 作用下， 以 乙醇 为溶剂， 反应 25.0h， 以86%的产率得到3β-hydroxy-7,12-diketo-5β-cholan-24-oic acid
  参考文献：
  名称：

  Preparative-scale regio- and stereospecific oxidoreduction of cholic acid and dehydrocholic acid catalyzed by hydroxysteroid dehydrogenases

  摘要：

  DOI：

  10.1021/jo00365a009

文献信息

• Kyogoku, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1937, vol. 250, p. 253,255
  作者：Kyogoku

  DOI：——

  日期：——
• Experimental verifications on chemical carcinogenesis, a bifunctional alkylation between DNA interstrands
  作者：Qianhuan Dai、Qingrong Zhang、Lihui Wang、Shu Pei、Qing Wang、Bo Qu

  DOI：10.1007/bf02887177

  日期：2000.6

  It is evidenced by the filter elution method that two carcinogenic aromatic hydrocarbons, benzo[a]pyrene and dibenzo[a,h]anthracene, two carcinogenic metal salts, beryllium chloride and cadmium chloride, four carcinogenic aromatic amines, 2-aminofluorene, beta-naphthylamine, 4-aminobiphenyl and benzidine, can all induce DNA interstrand and DNA-protein cross-link in L-1210 culture. However, under the same condition, the corresponding non-carcinogenic compounds, including benzo[k]fluorancene, anthracene, magnesium chloride, zinc chloride, alpha-naphthylamine, 2-aminobiphenyl and m-toluidine, cannot produce any cross-link adducts. Atl these results are consistent with the di-region theory that carcinogens are bio-bifunctional alkylation agents. This method can also be used to discriminate carcinogens and non-carcinogens.
• Yamasaki; Kyogoku, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1935, vol. 235, p. 43,45
  作者：Yamasaki、Kyogoku

  DOI：——

  日期：——
• Kazuno; Baba, Proceedings of the Japan Academy, 1951, vol. 27, p. 255,261
  作者：Kazuno、Baba

  DOI：——

  日期：——
• Cloning, tissue expression pattern characterization and chromosome localization of human peptide methionine sulfoxide reductase cDNA
  作者：Peirong Hu、Long Yu、Min Zhang、Lihua Zheng、Fei Lan、Qiang Fu、Shouyuan Zhao

  DOI：10.1007/bf02886363

  日期：2000.12

  Oxidation and reduction of some amino acids are one of the molecular mechanisms for regulating the function of proteins. The oxidation of methionine (Met) to methionine sulfoxide (Met(O)) results in decreasing or loss of the biological activity of related proteins. It was found that peptide methionine sulfoxide reductase (msrA) can reduce Met(O) to Met and therefore restored the biological function of the oxidized proteins. To reveal the methionine oxidation-reduction mechanism in human body, in this study the cDNA sequence of bovine msrA was used as an information-probe to screen the human EST database. Based on a contig assembled from homologous ESTs, a 1 256-bp human MSRA cDNA was cloned from several human cDNA libraries. The cDNA contains an open reading frame (ORF) of 705 bp in length, which encodes 235 amino acid residues. Homology comparison revealed that human MSRA shares 88% and 61% identities with bovine and Escherichia coli msrA protein respectively. Expression pattern analysis revealed a single 1.6-kb transcript of human MSRA in most human tissues and with highest expression in kidney. By radiation hybrid panel mapping, the gene was localized to human chromosome 8p22-23 between markers D8S518 and D8S550. There are 2 human inherited diseases Keratolytic Winter Erythema and Microcephaly related genes in this region, it is inferred that human MSRA might be the candidate of the two diseases.