Record Information |
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Version | 1.0 |
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Created at | 2024-01-10 20:05:28 UTC |
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Updated at | 2024-09-03 04:18:56 UTC |
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NP-MRD ID | NP0332355 |
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DOI | https://doi.org/10.57994/1569 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 5-alpha-cholestanol |
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Description | 5Alpha-Cholestanol, also known as cholestanol or dihydrocholesterol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 5alpha-cholestanol is considered to be a sterol. It was first documented in 2017 (PMID: 29066094). Based on a literature review a significant number of articles have been published on 5alpha-Cholestanol (PMID: 33891937) (PMID: 31653257) (PMID: 30940596) (PMID: 29334954). |
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Structure | [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C InChI=1S/C27H48O/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/h18-25,28H,6-17H2,1-5H3/t19-,20+,21+,22+,23-,24+,25+,26+,27-/m1/s1 |
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Synonyms | Value | Source |
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(3beta,5alpha)-Cholestan-3-ol | ChEBI | Cholestanol | ChEBI | Dihydrocholesterol | ChEBI | Zymostanol | ChEBI | (3b,5a)-Cholestan-3-ol | Generator | (3Β,5α)-cholestan-3-ol | Generator | 5a-Cholestanol | Generator | 5Α-cholestanol | Generator | 5 alpha Cholestan 3 beta ol | HMDB | 5 beta Cholestan 3 beta ol | HMDB | 5 beta-Cholestan-3 beta-ol | HMDB | beta Cholestanol | HMDB | beta-Ol, 5 beta-cholestan-3 | HMDB | 5 alpha Cholestan 3 alpha ol | HMDB | 5 alpha-Cholestan-3 beta-ol | HMDB | Cholestan 3 ol | HMDB | Cholestanol, (3alpha, 5beta)-isomer | HMDB | Coprosterol | HMDB | beta-Cholestanol | HMDB | 5 beta-Cholestan-3 alpha-ol | HMDB | Coprostanol | HMDB | 5 alpha-Cholestan-3 alpha-ol | HMDB | Cholestan-3-ol | HMDB | beta-Cholestan-3 beta-ol, 5 | HMDB | 3b-Hydroxy-5a-cholestane | HMDB | 3b-Hydroxycholestane | HMDB | 5a-Cholestan-3b-ol | HMDB | 5a-Dihydrocholesterol | HMDB | Cholestan-3b-ol | HMDB | Dihydrocholesterin | HMDB | Epicholestanol | HMDB | 5alpha-Cholestanol | ChEBI |
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Chemical Formula | C27H48O |
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Average Mass | 388.6694 Da |
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Monoisotopic Mass | 388.37052 Da |
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IUPAC Name | (1S,2S,5S,7S,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol |
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Traditional Name | (1S,2S,5S,7S,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C |
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InChI Identifier | InChI=1S/C27H48O/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/h18-25,28H,6-17H2,1-5H3/t19-,20+,21+,22+,23-,24+,25+,26+,27-/m1/s1 |
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InChI Key | QYIXCDOBOSTCEI-QCYZZNICSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | [13C, ] NMR Spectrum (2D, 201 MHz, CD3OD, experimental) | Not Available | Sumner lab, University of Missouri | Zach Tretter | 2024-01-10 | View Spectrum | 1D NMR | [1H, ] NMR Spectrum (2D, 800 MHz, CD3OD, experimental) | Not Available | Sumner lab, University of Missouri | Zach Tretter | 2024-01-10 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | Not Available |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. |
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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 | Cholestane steroids |
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Direct Parent | Cholesterols and derivatives |
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Alternative Parents | |
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Substituents | - Cholesterol-skeleton
- Cholesterol
- 3-beta-hydroxysteroid
- Hydroxysteroid
- 3-hydroxysteroid
- 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 | |
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Physical Properties |
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State | Not Available |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - Hoflinger P, Hauser S, Yutuc E, Hengel H, Griffiths L, Radelfahr F, Howell OW, Wang Y, Connor SL, Duell PB, DeBarber AE, Martus P, Lutjohann D, Griffiths WJ, Schols L: Metabolic profiling in serum, cerebrospinal fluid, and brain of patients with cerebrotendinous xanthomatosis. J Lipid Res. 2021;62:100078. doi: 10.1016/j.jlr.2021.100078. Epub 2021 Apr 20. [PubMed:33891937 ]
- Pecks U, Bornemann V, Klein A, Segger L, Maass N, Alkatout I, Eckmann-Scholz C, Elessawy M, Lutjohann D: Estimating fetal cholesterol synthesis rates by cord blood analysis in intrauterine growth restriction and normally grown fetuses. Lipids Health Dis. 2019 Oct 25;18(1):185. doi: 10.1186/s12944-019-1117-1. [PubMed:31653257 ]
- Lutjohann D, Bjorkhem I, Friedrichs S, Kerksiek A, Lovgren-Sandblom A, Geilenkeuser WJ, Ahrends R, Andrade I, Ansorena D, Astiasaran I, Baila-Rueda L, Barriuso B, Becker S, Bretillon L, Browne RW, Caccia C, Ceglarek U, Cenarro A, Crick PJ, Fauler G, Garcia-Llatas G, Gray R, Griffiths WJ, Gylling H, Harding S, Helmschrodt C, Iuliano L, Janssen HG, Jones P, Kaipiainen L, Kannenberg F, Lagarda MJ, Leoni V, Lottenberg AM, MacKay DS, Matysik S, McDonald J, Menendez-Carreno M, Myrie SB, Sutti Nunes V, Ostlund RE, Polisecki E, Ramos F, Rideout TC, Schaefer EJ, Schmitz G, Wang Y, Zerbinati C, Diczfalusy U, Schott HF: First international descriptive and interventional survey for cholesterol and non-cholesterol sterol determination by gas- and liquid-chromatography-Urgent need for harmonisation of analytical methods. J Steroid Biochem Mol Biol. 2019 Jun;190:115-125. doi: 10.1016/j.jsbmb.2019.03.025. Epub 2019 Mar 30. [PubMed:30940596 ]
- Baila-Rueda L, Lamiquiz-Moneo I, Jarauta E, Mateo-Gallego R, Perez-Calahorra S, Marco-Benedi V, Bea AM, Cenarro A, Civeira F: Association between non-cholesterol sterol concentrations and Achilles tendon thickness in patients with genetic familial hypercholesterolemia. J Transl Med. 2018 Jan 15;16(1):6. doi: 10.1186/s12967-018-1380-3. [PubMed:29334954 ]
- Lamiquiz-Moneo I, Baila-Rueda L, Bea AM, Mateo-Gallego R, Perez-Calahorra S, Marco-Benedi V, Martin-Navarro A, Ros E, Cofan M, Rodriguez-Rey JC, Pocovi M, Cenarro A, Civeira F: ABCG5/G8 gene is associated with hypercholesterolemias without mutation in candidate genes and noncholesterol sterols. J Clin Lipidol. 2017 Nov-Dec;11(6):1432-1440.e4. doi: 10.1016/j.jacl.2017.09.005. Epub 2017 Oct 4. [PubMed:29066094 ]
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