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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-14 18:14:34 UTC
Update Date2022-03-07 02:49:34 UTC
HMDB IDHMDB0006894
Secondary Accession Numbers
  • HMDB06894
Metabolite Identification
Common Name3a,7a-Dihydroxy-5b-cholestan-26-al
Description3alpha,7alpha-Dihydroxy-5beta-cholestan-26-al is an intermediate involved in bile acid biosynthesis, specifically in the synthesis of chenodeoxyglycocholate and lithocholate. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, depending only on the presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g. membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues (PMID: 11316487 , 16037564 , 12576301 , 11907135 ).
Structure
Data?1582752413
Synonyms
ValueSource
3alpha,7alpha-Dihydroxy-5beta-cholestan-27-alHMDB
5beta-Cholestan-27-al-3alpha,7alpha-diolHMDB
5beta-Cholestane-3alpha,7alpha-diol-27-alHMDB
Chemical FormulaC27H46O3
Average Molecular Weight418.6523
Monoisotopic Molecular Weight418.344695338
IUPAC Name6-[(2S,5R,9R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2-methylheptanal
Traditional Name6-[(2S,5R,9R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2-methylheptanal
CAS Registry NumberNot Available
SMILES
CC(CCCC(C)C1CCC2C3[C@H](O)CC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C)C=O
InChI Identifier
InChI=1S/C27H46O3/c1-17(16-28)6-5-7-18(2)21-8-9-22-25-23(11-13-27(21,22)4)26(3)12-10-20(29)14-19(26)15-24(25)30/h16-25,29-30H,5-15H2,1-4H3/t17?,18?,19?,20-,21?,22?,23?,24-,25?,26+,27-/m1/s1
InChI KeyYWGOKHMOJTZGBN-SBOSHUFNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentDihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • 27-oxosteroid
  • 26-oxosteroid
  • Dihydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • Hydroxysteroid
  • Oxosteroid
  • 3-alpha-hydroxysteroid
  • 7-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aldehyde
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0007 g/LALOGPS
logP4.91ALOGPS
logP4.99ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)16.07ChemAxon
pKa (Strongest Basic)-0.54ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity122.12 m³·mol⁻¹ChemAxon
Polarizability51.14 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+200.72431661259
DarkChem[M-H]-197.47831661259
DeepCCS[M-2H]-237.06430932474
DeepCCS[M+Na]+212.41330932474
AllCCS[M+H]+209.732859911
AllCCS[M+H-H2O]+207.832859911
AllCCS[M+NH4]+211.532859911
AllCCS[M+Na]+212.032859911
AllCCS[M-H]-204.032859911
AllCCS[M+Na-2H]-206.032859911
AllCCS[M+HCOO]-208.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3a,7a-Dihydroxy-5b-cholestan-26-alCC(CCCC(C)C1CCC2C3[C@H](O)CC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C)C=O2617.0Standard polar33892256
3a,7a-Dihydroxy-5b-cholestan-26-alCC(CCCC(C)C1CCC2C3[C@H](O)CC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C)C=O3418.1Standard non polar33892256
3a,7a-Dihydroxy-5b-cholestan-26-alCC(CCCC(C)C1CCC2C3[C@H](O)CC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C)C=O3566.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3a,7a-Dihydroxy-5b-cholestan-26-al,1TMS,isomer #1CC(C=O)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O)CC1C[C@H]3O[Si](C)(C)C3566.9Semi standard non polar33892256
3a,7a-Dihydroxy-5b-cholestan-26-al,1TMS,isomer #2CC(C=O)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)CC1C[C@H]3O3556.1Semi standard non polar33892256
3a,7a-Dihydroxy-5b-cholestan-26-al,1TMS,isomer #3CC(=CO[Si](C)(C)C)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O)CC1C[C@H]3O3623.3Semi standard non polar33892256
3a,7a-Dihydroxy-5b-cholestan-26-al,2TMS,isomer #1CC(C=O)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)CC1C[C@H]3O[Si](C)(C)C3544.0Semi standard non polar33892256
3a,7a-Dihydroxy-5b-cholestan-26-al,2TMS,isomer #2CC(=CO[Si](C)(C)C)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O)CC1C[C@H]3O[Si](C)(C)C3565.4Semi standard non polar33892256
3a,7a-Dihydroxy-5b-cholestan-26-al,2TMS,isomer #3CC(=CO[Si](C)(C)C)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)CC1C[C@H]3O3604.5Semi standard non polar33892256
3a,7a-Dihydroxy-5b-cholestan-26-al,3TMS,isomer #1CC(=CO[Si](C)(C)C)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)CC1C[C@H]3O[Si](C)(C)C3524.5Semi standard non polar33892256
3a,7a-Dihydroxy-5b-cholestan-26-al,3TMS,isomer #1CC(=CO[Si](C)(C)C)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)CC1C[C@H]3O[Si](C)(C)C3437.5Standard non polar33892256
3a,7a-Dihydroxy-5b-cholestan-26-al,3TMS,isomer #1CC(=CO[Si](C)(C)C)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)CC1C[C@H]3O[Si](C)(C)C3653.3Standard polar33892256
3a,7a-Dihydroxy-5b-cholestan-26-al,1TBDMS,isomer #1CC(C=O)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O)CC1C[C@H]3O[Si](C)(C)C(C)(C)C3763.9Semi standard non polar33892256
3a,7a-Dihydroxy-5b-cholestan-26-al,1TBDMS,isomer #2CC(C=O)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1C[C@H]3O3774.0Semi standard non polar33892256
3a,7a-Dihydroxy-5b-cholestan-26-al,1TBDMS,isomer #3CC(=CO[Si](C)(C)C(C)(C)C)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O)CC1C[C@H]3O3859.2Semi standard non polar33892256
3a,7a-Dihydroxy-5b-cholestan-26-al,2TBDMS,isomer #1CC(C=O)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1C[C@H]3O[Si](C)(C)C(C)(C)C3951.9Semi standard non polar33892256
3a,7a-Dihydroxy-5b-cholestan-26-al,2TBDMS,isomer #2CC(=CO[Si](C)(C)C(C)(C)C)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O)CC1C[C@H]3O[Si](C)(C)C(C)(C)C3977.0Semi standard non polar33892256
3a,7a-Dihydroxy-5b-cholestan-26-al,2TBDMS,isomer #3CC(=CO[Si](C)(C)C(C)(C)C)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1C[C@H]3O4046.7Semi standard non polar33892256
3a,7a-Dihydroxy-5b-cholestan-26-al,3TBDMS,isomer #1CC(=CO[Si](C)(C)C(C)(C)C)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1C[C@H]3O[Si](C)(C)C(C)(C)C4149.0Semi standard non polar33892256
3a,7a-Dihydroxy-5b-cholestan-26-al,3TBDMS,isomer #1CC(=CO[Si](C)(C)C(C)(C)C)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1C[C@H]3O[Si](C)(C)C(C)(C)C4080.9Standard non polar33892256
3a,7a-Dihydroxy-5b-cholestan-26-al,3TBDMS,isomer #1CC(=CO[Si](C)(C)C(C)(C)C)CCCC(C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1C[C@H]3O[Si](C)(C)C(C)(C)C3880.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3a,7a-Dihydroxy-5b-cholestan-26-al GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kmu-0339300000-0fd6122a26503368155c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3a,7a-Dihydroxy-5b-cholestan-26-al GC-MS (2 TMS) - 70eV, Positivesplash10-0002-1120590000-71303e88e12ed44c4b562017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3a,7a-Dihydroxy-5b-cholestan-26-al GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a-Dihydroxy-5b-cholestan-26-al 10V, Positive-QTOFsplash10-0uxr-0004900000-ca25d351c3a9b92dc2962017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a-Dihydroxy-5b-cholestan-26-al 20V, Positive-QTOFsplash10-0v59-2029300000-1c0f62a67ae4742259d12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a-Dihydroxy-5b-cholestan-26-al 40V, Positive-QTOFsplash10-0103-1039000000-6831e5ba2d41d656a8e92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a-Dihydroxy-5b-cholestan-26-al 10V, Negative-QTOFsplash10-014i-0004900000-7e27ef5ddfd709cb4b8f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a-Dihydroxy-5b-cholestan-26-al 20V, Negative-QTOFsplash10-014j-0009700000-011533bdc49b83a6066d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a-Dihydroxy-5b-cholestan-26-al 40V, Negative-QTOFsplash10-0a4i-9007100000-dd7725ab58a61707d9572017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a-Dihydroxy-5b-cholestan-26-al 10V, Negative-QTOFsplash10-014i-0001900000-533307303621a2503ba12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a-Dihydroxy-5b-cholestan-26-al 20V, Negative-QTOFsplash10-014i-0005900000-9f688b3a77a79abcc6cd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a-Dihydroxy-5b-cholestan-26-al 40V, Negative-QTOFsplash10-014i-0001900000-7c170a7ab1413b313dce2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a-Dihydroxy-5b-cholestan-26-al 10V, Positive-QTOFsplash10-0gb9-2103900000-f873024c14cbeb7d6b072021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a-Dihydroxy-5b-cholestan-26-al 20V, Positive-QTOFsplash10-0089-5119100000-1c609480a256fe41f4dd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a-Dihydroxy-5b-cholestan-26-al 40V, Positive-QTOFsplash10-066s-9530000000-e723274715d0b31199dd2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024141
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC05445
BioCyc IDNot Available
BiGG ID45826
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477906
PDB IDNot Available
ChEBI ID27428
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86. [PubMed:11316487 ]
  2. Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. Epub 2005 Jul 21. [PubMed:16037564 ]
  3. Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56. [PubMed:12576301 ]
  4. Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43. [PubMed:11907135 ]

Only showing the first 10 proteins. There are 13 proteins in total.

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Converts gamma-trimethylaminobutyraldehyde into gamma-butyrobetaine. Catalyzes the irreversible oxidation of a broad range of aldehydes to the corresponding acids in an NAD-dependent reaction.
Gene Name:
ALDH9A1
Uniprot ID:
P49189
Molecular weight:
56291.485
Reactions
3a,7a-Dihydroxy-5b-cholestan-26-al + NAD + Water → 17alpha,20alpha-Dihydroxypregn-4-en-3-one + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Molecular weight:
58486.74
Reactions
3a,7a-Dihydroxy-5b-cholestan-26-al + NAD + Water → 17alpha,20alpha-Dihydroxypregn-4-en-3-one + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Reactions
3a,7a-Dihydroxy-5b-cholestan-26-al + NAD + Water → 17alpha,20alpha-Dihydroxypregn-4-en-3-one + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Molecular weight:
54847.36
Reactions
3a,7a-Dihydroxy-5b-cholestan-26-al + NAD + Water → 17alpha,20alpha-Dihydroxypregn-4-en-3-one + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96
Reactions
3a,7a-Dihydroxy-5b-cholestan-26-al + NAD + Water → 17alpha,20alpha-Dihydroxypregn-4-en-3-one + NADH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Class-III ADH is remarkably ineffective in oxidizing ethanol, but it readily catalyzes the oxidation of long-chain primary alcohols and the oxidation of S-(hydroxymethyl) glutathione.
Gene Name:
ADH5
Uniprot ID:
P11766
Molecular weight:
39723.945
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH1B
Uniprot ID:
P00325
Molecular weight:
39835.17
General function:
Involved in zinc ion binding
Specific function:
Could function in retinol oxidation for the synthesis of retinoic acid, a hormone important for cellular differentiation. Medium-chain (octanol) and aromatic (m-nitrobenzaldehyde) compounds are the best substrates. Ethanol is not a good substrate but at the high ethanol concentrations reached in the digestive tract, it plays a role in the ethanol oxidation and contributes to the first pass ethanol metabolism.
Gene Name:
ADH7
Uniprot ID:
P40394
Molecular weight:
41480.985
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH1A
Uniprot ID:
P07327
Molecular weight:
39858.37

Only showing the first 10 proteins. There are 13 proteins in total.