Np mrd loader

Record Information
Version2.0
Created at2024-01-10 20:05:28 UTC
Updated at2024-09-03 04:18:56 UTC
NP-MRD IDNP0332355
Natural Product DOIhttps://doi.org/10.57994/1569
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-alpha-cholestanol
Description5Alpha-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. 5-alpha-cholestanol was first documented in 2017 (PMID: 29066094). Based on a literature review a small amount of articles have been published on 5alpha-Cholestanol (PMID: 33891937) (PMID: 31653257) (PMID: 30940596) (PMID: 29334954).
Structure
Thumb
Synonyms
ValueSource
(3beta,5alpha)-Cholestan-3-olChEBI
CholestanolChEBI
DihydrocholesterolChEBI
ZymostanolChEBI
(3b,5a)-Cholestan-3-olGenerator
(3Β,5α)-cholestan-3-olGenerator
5a-CholestanolGenerator
5Α-cholestanolGenerator
5 alpha Cholestan 3 beta olHMDB
5 beta Cholestan 3 beta olHMDB
5 beta-Cholestan-3 beta-olHMDB
beta CholestanolHMDB
beta-Ol, 5 beta-cholestan-3HMDB
5 alpha Cholestan 3 alpha olHMDB
5 alpha-Cholestan-3 beta-olHMDB
Cholestan 3 olHMDB
Cholestanol, (3alpha, 5beta)-isomerHMDB
CoprosterolHMDB
beta-CholestanolHMDB
5 beta-Cholestan-3 alpha-olHMDB
CoprostanolHMDB
5 alpha-Cholestan-3 alpha-olHMDB
Cholestan-3-olHMDB
beta-Cholestan-3 beta-ol, 5HMDB
3b-Hydroxy-5a-cholestaneHMDB
3b-HydroxycholestaneHMDB
5a-Cholestan-3b-olHMDB
5a-DihydrocholesterolHMDB
Cholestan-3b-olHMDB
DihydrocholesterinHMDB
EpicholestanolHMDB
5alpha-CholestanolChEBI
Chemical FormulaC27H48O
Average Mass388.6694 Da
Monoisotopic Mass388.37052 Da
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
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
CAS Registry NumberNot Available
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
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
InChI KeyQYIXCDOBOSTCEI-QCYZZNICSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)Not AvailableSumner lab, University of MissouriZach Tretter2024-01-10View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, CD3OD, experimental)Not AvailableSumner lab, University of MissouriZach Tretter2024-01-10View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
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
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.02ALOGPS
logP7.52ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity119.77 m³·mol⁻¹ChemAxon
Polarizability51.27 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000908
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012122
KNApSAcK IDC00053136
Chemspider ID6413
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5864
PubChem Compound6665
PDB IDNot Available
ChEBI ID86570
Good Scents IDrw1133261
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]