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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-12 23:14:06 UTC
Update Date2022-03-07 02:49:18 UTC
HMDB IDHMDB0003533
Secondary Accession Numbers
  • HMDB0006263
  • HMDB03533
  • HMDB06263
Metabolite Identification
Common Name3a,7a,12a-Trihydroxy-5b-cholestan-26-al
Description3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestan-26-al is an intermediate in bile acid biosynthesis. 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 ). 3a,7a,12a-trihydroxy-5b-cholestane-27-al is an enzymatically generated intermediate in the oxidation process of 5b-cholestane-3a,7a,12a,27-tetrol into 3a,7a,12a-trihydroxy-5b-cholestanoic acid in liver mitochondria. Mitochondrial sterol 27-hydroxylase (EC 1.14.13.60) appears to perform multiple monooxygenations in this conversion. (PMID: 8496170 ).
Structure
Data?1582752280
Synonyms
ValueSource
(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholestan-26-alChEBI
3,7,12-Trihydroxycholestan-26-alChEBI
(3a,5b,7a,12a)-3,7,12-Trihydroxycholestan-26-alGenerator
(3Α,5β,7α,12α)-3,7,12-trihydroxycholestan-26-alGenerator
(6R)-2-Methyl-6-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]heptanalHMDB
3-alpha-7-alpha-12-alpha-Trihydroxy-5-beta-cholestan-26-alHMDB
3alpha,7-alpha,12alpha-Trihydroxy-5beta-cholestan-26-alHMDB
3 alpha,7-alpha,12 alpha-Trihydroxy-5 beta-cholestan-26-alHMDB
Chemical FormulaC27H46O4
Average Molecular Weight434.6517
Monoisotopic Molecular Weight434.33960996
IUPAC Name(6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanal
Traditional Name(6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanal
CAS Registry Number3836-01-9
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)C=O
InChI Identifier
InChI=1S/C27H46O4/c1-16(15-28)6-5-7-17(2)20-8-9-21-25-22(14-24(31)27(20,21)4)26(3)11-10-19(29)12-18(26)13-23(25)30/h15-25,29-31H,5-14H2,1-4H3/t16?,17-,18+,19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChI KeyUSFJGINJGUIFSY-XZULNKEGSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTrihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • 27-oxosteroid
  • 26-oxosteroid
  • Trihydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • 12-hydroxysteroid
  • Hydroxysteroid
  • Oxosteroid
  • 3-alpha-hydroxysteroid
  • 7-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aldehyde
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP4.265Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP3.92ALOGPS
logP3.76ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)16.07ChemAxon
pKa (Strongest Basic)-0.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity123.64 m³·mol⁻¹ChemAxon
Polarizability52.42 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]+201.36531661259
DarkChem[M-H]-194.99531661259
DeepCCS[M-2H]-243.59430932474
DeepCCS[M+Na]+217.61230932474
AllCCS[M+H]+212.032859911
AllCCS[M+H-H2O]+210.232859911
AllCCS[M+NH4]+213.732859911
AllCCS[M+Na]+214.232859911
AllCCS[M-H]-205.932859911
AllCCS[M+Na-2H]-208.132859911
AllCCS[M+HCOO]-210.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3a,7a,12a-Trihydroxy-5b-cholestan-26-al[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)C=O2993.2Standard polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)C=O3576.6Standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)C=O3828.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,1TMS,isomer #1CC(C=O)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C3496.3Semi standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,1TMS,isomer #2CC(C=O)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O3554.2Semi standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,1TMS,isomer #3CC(C=O)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O3547.2Semi standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,1TMS,isomer #4CC(=CO[Si](C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O3642.9Semi standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,2TMS,isomer #1CC(C=O)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C3485.2Semi standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,2TMS,isomer #2CC(C=O)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C3465.7Semi standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,2TMS,isomer #3CC(=CO[Si](C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C3520.4Semi standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,2TMS,isomer #4CC(C=O)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O3496.9Semi standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,2TMS,isomer #5CC(=CO[Si](C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O3615.2Semi standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,2TMS,isomer #6CC(=CO[Si](C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O3585.1Semi standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,3TMS,isomer #1CC(C=O)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C3469.0Semi standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,3TMS,isomer #2CC(=CO[Si](C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C3522.8Semi standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,3TMS,isomer #3CC(=CO[Si](C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C3519.8Semi standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,3TMS,isomer #4CC(=CO[Si](C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O3529.0Semi standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,4TMS,isomer #1CC(=CO[Si](C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C3514.7Semi standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,4TMS,isomer #1CC(=CO[Si](C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C3433.0Standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,4TMS,isomer #1CC(=CO[Si](C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C3580.7Standard polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,1TBDMS,isomer #1CC(C=O)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C3720.9Semi standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,1TBDMS,isomer #2CC(C=O)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O3778.4Semi standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,1TBDMS,isomer #3CC(C=O)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O3775.3Semi standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,1TBDMS,isomer #4CC(=CO[Si](C)(C)C(C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O3865.6Semi standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,2TBDMS,isomer #1CC(C=O)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C3933.3Semi standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,2TBDMS,isomer #2CC(C=O)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C3904.4Semi standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,2TBDMS,isomer #3CC(=CO[Si](C)(C)C(C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C3935.9Semi standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,2TBDMS,isomer #4CC(C=O)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O3940.6Semi standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,2TBDMS,isomer #5CC(=CO[Si](C)(C)C(C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O4068.7Semi standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,2TBDMS,isomer #6CC(=CO[Si](C)(C)C(C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O4018.8Semi standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,3TBDMS,isomer #1CC(C=O)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C4120.5Semi standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,3TBDMS,isomer #2CC(=CO[Si](C)(C)C(C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C4159.0Semi standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,3TBDMS,isomer #3CC(=CO[Si](C)(C)C(C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C4143.1Semi standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,3TBDMS,isomer #4CC(=CO[Si](C)(C)C(C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O4188.6Semi standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,4TBDMS,isomer #1CC(=CO[Si](C)(C)C(C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C4374.2Semi standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,4TBDMS,isomer #1CC(=CO[Si](C)(C)C(C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C4147.6Standard non polar33892256
3a,7a,12a-Trihydroxy-5b-cholestan-26-al,4TBDMS,isomer #1CC(=CO[Si](C)(C)C(C)(C)C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C3848.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholestan-26-al GC-MS (Non-derivatized) - 70eV, Positivesplash10-05n0-0539800000-e17f084e0678cd71fce82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholestan-26-al GC-MS (3 TMS) - 70eV, Positivesplash10-000i-0313149000-8f4c3fec7b662dbf46d22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3a,7a,12a-Trihydroxy-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,12a-Trihydroxy-5b-cholestan-26-al 10V, Positive-QTOFsplash10-014j-0006900000-8f907fe536c81d1166ad2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholestan-26-al 20V, Positive-QTOFsplash10-00kb-1019300000-780bb9b9d55b812930c42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholestan-26-al 40V, Positive-QTOFsplash10-000i-2009000000-9b52601f913e3bbb4c0a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholestan-26-al 10V, Negative-QTOFsplash10-001i-0001900000-4383dce4ba8c45585b482017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholestan-26-al 20V, Negative-QTOFsplash10-0159-0002900000-fbc50593e1905290155e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholestan-26-al 40V, Negative-QTOFsplash10-0a4r-9005300000-07a48968e6731add21f72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholestan-26-al 10V, Positive-QTOFsplash10-00ks-1006900000-2471d92ac4c323289c672021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholestan-26-al 20V, Positive-QTOFsplash10-000i-4249200000-0b7ecbecd8f67217ea562021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholestan-26-al 40V, Positive-QTOFsplash10-0a4i-9621000000-17c980384d97d3d72a102021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholestan-26-al 10V, Negative-QTOFsplash10-001i-0001900000-a283ea4f75f642471b3c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholestan-26-al 20V, Negative-QTOFsplash10-001i-0001900000-d7676b1fba2f6b906efc2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholestan-26-al 40V, Negative-QTOFsplash10-001i-0023900000-ebbdce292f968247b51d2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
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 IDFDB023188
KNApSAcK IDNot Available
Chemspider ID388578
KEGG Compound IDC01301
BioCyc IDNot Available
BiGG ID37315
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439479
PDB IDNot Available
ChEBI ID16466
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceDayal B; Tint G S; Batta A K; Shefer S; Salen G Synthesis of biological precursors of cholic acid II. Steroids (1981), 37(2), 205-11.
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 ]
  5. Holmberg-Betsholtz I, Lund E, Bjorkhem I, Wikvall K: Sterol 27-hydroxylase in bile acid biosynthesis. Mechanism of oxidation of 5 beta-cholestane-3 alpha,7 alpha,12 alpha,27-tetrol into 3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholestanoic acid. J Biol Chem. 1993 May 25;268(15):11079-85. [PubMed:8496170 ]
  6. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the first step in the oxidation of the side chain of sterol intermediates; the 27-hydroxylation of 5-beta-cholestane-3-alpha,7-alpha,12-alpha-triol. Has also a vitamin D3-25-hydroxylase activity.
Gene Name:
CYP27A1
Uniprot ID:
Q02318
Molecular weight:
60234.28
Reactions
27-Deoxy-5b-cyprinol → 3a,7a,12a-Trihydroxy-5b-cholestan-26-aldetails
3a,7a,12a-Trihydroxy-5b-cholestan-26-al + NADPH + Oxygen + Hydrogen Ion → Coprocholic acid + NADP + Waterdetails