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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-14 17:57:44 UTC
Update Date2021-09-14 15:19:03 UTC
HMDB IDHMDB0006887
Secondary Accession Numbers
  • HMDB06887
Metabolite Identification
Common Name7a,12a-Dihydroxy-5b-cholestan-3-one
Description7alpha,12alpha-Dihydroxy-5beta-cholestan-3-one 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 ).
Structure
Data?1582752412
Synonyms
ValueSource
5b-Cholestane-7a,12a-diol-3-oneHMDB
5beta-Cholestane-7alpha,12alpha-diol-3-oneHMDB
7alpha,12alpha-Dihydroxy-5beta-cholestan-3-oneHMDB
Chemical FormulaC27H46O3
Average Molecular Weight418.6523
Monoisotopic Molecular Weight418.344695338
IUPAC Name(1S,2S,9R,11R,15R)-9,16-dihydroxy-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one
Traditional Name(1S,2S,9R,11R,15R)-9,16-dihydroxy-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one
CAS Registry NumberNot Available
SMILES
[H][C@]12CCC(C(C)CCCC(C)C)[C@@]1(C)C([H])(O)C[C@@]1([H])C2[C@H](O)CC2CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C27H46O3/c1-16(2)7-6-8-17(3)20-9-10-21-25-22(15-24(30)27(20,21)5)26(4)12-11-19(28)13-18(26)14-23(25)29/h16-18,20-25,29-30H,6-15H2,1-5H3/t17?,18?,20?,21-,22+,23-,24-,25?,26+,27-/m1/s1
InChI KeyHHVQPBXBALLUDF-JEUKKHAPSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerolipids
Sub ClassDiradylglycerols
Direct Parent1,2-diacylglycerols
Alternative Parents
Substituents
  • 1,2-acyl-sn-glycerol
  • Fatty acid ester
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0035 g/LALOGPS
logP10(4.73) g/LALOGPS
logP10(5.19) g/LChemAxon
logS10(-5.1) g/LALOGPS
pKa (Strongest Acidic)19.99ChemAxon
pKa (Strongest Basic)-0.18ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity121.85 m³·mol⁻¹ChemAxon
Polarizability51.38 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+203.41831661259
DarkChem[M-H]-199.82431661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
7a,12a-Dihydroxy-5b-cholestan-3-one,1TMS,#1CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O[Si](C)(C)C)[C@]12C)[C@@]1(C)CCC(=O)CC1C[C@H]3O3464.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a,12a-Dihydroxy-5b-cholestan-3-one,1TMS,#2CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O)[C@]12C)[C@@]1(C)CCC(=O)CC1C[C@H]3O[Si](C)(C)C3473.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a,12a-Dihydroxy-5b-cholestan-3-one,1TMS,#3CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O)[C@]12C)[C@@]1(C)CC=C(O[Si](C)(C)C)CC1C[C@H]3O3422.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a,12a-Dihydroxy-5b-cholestan-3-one,1TMS,#4CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O)[C@]12C)[C@@]1(C)CCC(O[Si](C)(C)C)=CC1C[C@H]3O3423.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a,12a-Dihydroxy-5b-cholestan-3-one,2TMS,#1CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O[Si](C)(C)C)[C@]12C)[C@@]1(C)CCC(=O)CC1C[C@H]3O[Si](C)(C)C3388.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a,12a-Dihydroxy-5b-cholestan-3-one,2TMS,#2CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O[Si](C)(C)C)[C@]12C)[C@@]1(C)CCC(O[Si](C)(C)C)=CC1C[C@H]3O3386.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a,12a-Dihydroxy-5b-cholestan-3-one,2TMS,#3CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O[Si](C)(C)C)[C@]12C)[C@@]1(C)CC=C(O[Si](C)(C)C)CC1C[C@H]3O3372.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a,12a-Dihydroxy-5b-cholestan-3-one,2TMS,#4CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O)[C@]12C)[C@@]1(C)CCC(O[Si](C)(C)C)=CC1C[C@H]3O[Si](C)(C)C3390.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a,12a-Dihydroxy-5b-cholestan-3-one,2TMS,#5CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O)[C@]12C)[C@@]1(C)CC=C(O[Si](C)(C)C)CC1C[C@H]3O[Si](C)(C)C3387.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a,12a-Dihydroxy-5b-cholestan-3-one,1TBDMS,#1CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O[Si](C)(C)C(C)(C)C)[C@]12C)[C@@]1(C)CCC(=O)CC1C[C@H]3O3677.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a,12a-Dihydroxy-5b-cholestan-3-one,1TBDMS,#2CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O)[C@]12C)[C@@]1(C)CCC(=O)CC1C[C@H]3O[Si](C)(C)C(C)(C)C3693.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a,12a-Dihydroxy-5b-cholestan-3-one,1TBDMS,#3CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O)[C@]12C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)CC1C[C@H]3O3670.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a,12a-Dihydroxy-5b-cholestan-3-one,1TBDMS,#4CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O)[C@]12C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=CC1C[C@H]3O3668.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a,12a-Dihydroxy-5b-cholestan-3-one,2TBDMS,#1CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O[Si](C)(C)C(C)(C)C)[C@]12C)[C@@]1(C)CCC(=O)CC1C[C@H]3O[Si](C)(C)C(C)(C)C3795.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a,12a-Dihydroxy-5b-cholestan-3-one,2TBDMS,#2CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O[Si](C)(C)C(C)(C)C)[C@]12C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=CC1C[C@H]3O3858.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a,12a-Dihydroxy-5b-cholestan-3-one,2TBDMS,#3CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O[Si](C)(C)C(C)(C)C)[C@]12C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)CC1C[C@H]3O3833.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a,12a-Dihydroxy-5b-cholestan-3-one,2TBDMS,#4CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O)[C@]12C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=CC1C[C@H]3O[Si](C)(C)C(C)(C)C3862.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a,12a-Dihydroxy-5b-cholestan-3-one,2TBDMS,#5CC(C)CCCC(C)C1CC[C@@H]2C3[C@H](CC(O)[C@]12C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)CC1C[C@H]3O[Si](C)(C)C(C)(C)C3855.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 7a,12a-Dihydroxy-5b-cholestan-3-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fk9-0549200000-dceadac2ca32e85a9fdd2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7a,12a-Dihydroxy-5b-cholestan-3-one GC-MS (2 TMS) - 70eV, Positivesplash10-0002-5542590000-b45c345b88b2b3b46f032017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7a,12a-Dihydroxy-5b-cholestan-3-one GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7a,12a-Dihydroxy-5b-cholestan-3-one 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 - 7a,12a-Dihydroxy-5b-cholestan-3-one 10V, Positive-QTOFsplash10-0uxr-0005900000-9f54eab9eecc22e267132017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-5b-cholestan-3-one 20V, Positive-QTOFsplash10-0ul3-3209300000-09494edc1c2008eab65e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-5b-cholestan-3-one 40V, Positive-QTOFsplash10-0ab9-5209000000-ede875adbb4dc1186f602017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-5b-cholestan-3-one 10V, Negative-QTOFsplash10-014i-0004900000-bf213248ab899a2b7bee2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-5b-cholestan-3-one 20V, Negative-QTOFsplash10-014j-0008900000-2d5e0f8ee4e8dbf0e7b52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-5b-cholestan-3-one 40V, Negative-QTOFsplash10-0f79-2109200000-af8562b835f573a2f41e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-5b-cholestan-3-one 10V, Positive-QTOFsplash10-014i-1002900000-25d4c3065d4dd09436362021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-5b-cholestan-3-one 20V, Positive-QTOFsplash10-0kui-9246500000-f173aa82bf42c825c9782021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-5b-cholestan-3-one 40V, Positive-QTOFsplash10-0a4i-9510000000-81b09eb12b57d9f340052021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-5b-cholestan-3-one 10V, Negative-QTOFsplash10-014i-0000900000-f2cb6399034352e924c82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-5b-cholestan-3-one 20V, Negative-QTOFsplash10-014i-0001900000-fbf80cd6881af08fa3a62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,12a-Dihydroxy-5b-cholestan-3-one 40V, Negative-QTOFsplash10-014i-0029500000-3c9e6f7da209a7490e5f2021-09-22Wishart 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 IDFDB024587
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
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 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid dehydrogenase activity. The biotransformation of the pesticide chlordecone (kepone) to its corresponding alcohol leads to increased biliary excretion of the pesticide and concomitant reduction of its neurotoxicity since bile is the major excretory route.
Gene Name:
AKR1C4
Uniprot ID:
P17516
Molecular weight:
37094.57
Reactions
5beta-Cholestane-3alpha,7alpha,12alpha-triol + NAD → 7a,12a-Dihydroxy-5b-cholestan-3-one + NADH + Hydrogen Iondetails
5beta-Cholestane-3alpha,7alpha,12alpha-triol + NADP → 7a,12a-Dihydroxy-5b-cholestan-3-one + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihydroxy-4-cholesten-3-one and 7-alpha-hydroxy-4-cholesten-3-one can also act as substrates.
Gene Name:
AKR1D1
Uniprot ID:
P51857
Molecular weight:
32889.38
Reactions
7a,12a-Dihydroxy-5b-cholestan-3-one + NADP → 7a,12a-Dihydroxy-cholestene-3-one + NADPH + Hydrogen Iondetails
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