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Showing Compound 3a,7a,12a-Trihydroxy-5b-cholestan-26-al (FDB023188)

Record Information
Version1.0
Creation date2011-09-21 00:25:57 UTC
Update date2015-07-21 06:57:35 UTC
Primary IDFDB023188
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 bile of mammals. The distinction between different bile acids is minute, depends only on 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) [HMDB]
CAS Number3836-01-9
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(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
(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,7alpha,12alpha-Trihydroxy-5beta-cholestan-26-alChEBI
3α,7α,12α-trihydroxy-5β-cholestan-26-alGenerator
Predicted 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
Chemical FormulaC27H46O4
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
InChI IdentifierInChI=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
Isomeric 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
Average Molecular Weight434.6517
Monoisotopic Molecular Weight434.33960996
Classification
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
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS3a,7a,12a-Trihydroxy-5b-cholestan-26-al, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05n0-0539800000-e17f084e0678cd71fce8Spectrum
Predicted GC-MS3a,7a,12a-Trihydroxy-5b-cholestan-26-al, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-0313149000-8f4c3fec7b662dbf46d2Spectrum
Predicted GC-MS3a,7a,12a-Trihydroxy-5b-cholestan-26-al, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0006900000-8f907fe536c81d1166ad2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-1019300000-780bb9b9d55b812930c42017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2009000000-9b52601f913e3bbb4c0a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0001900000-4383dce4ba8c45585b482017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0159-0002900000-fbc50593e1905290155e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-9005300000-07a48968e6731add21f72017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ks-1006900000-2471d92ac4c323289c672021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-4249200000-0b7ecbecd8f67217ea562021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9621000000-17c980384d97d3d72a102021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0001900000-a283ea4f75f642471b3c2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0001900000-d7676b1fba2f6b906efc2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0023900000-ebbdce292f968247b51d2021-09-25View Spectrum
NMRNot Available
ChemSpider ID388578
ChEMBL IDNot Available
KEGG Compound IDC01301
Pubchem Compound ID439479
Pubchem Substance IDNot Available
ChEBI ID16466
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03533
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID37315
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Bile Acid BiosynthesisSMP00035 map00120
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference