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Showing metabocard for 3b,5a,6b-Cholestanetriol (HMDB0003990)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-13 08:39:17 UTC
Update Date2022-03-07 02:49:20 UTC
HMDB IDHMDB0003990
Secondary Accession Numbers
  • HMDB03990
Metabolite Identification
Common Name3b,5a,6b-Cholestanetriol
Description3b,5a,6b-Cholestanetriol is a product of cholesterol oxidation found in human plasma.
Structure
Data?1582752294
MOLSDFPDBSMILESInChI

MOL for HMDB0003990 (3b,5a,6b-Cholestanetriol)

Not Available

3D MOL for HMDB0003990 (3b,5a,6b-Cholestanetriol)

Not Available

3D SDF for HMDB0003990 (3b,5a,6b-Cholestanetriol)

Not Available

3D-SDF for HMDB0003990 (3b,5a,6b-Cholestanetriol)

Not Available

PDB for HMDB0003990 (3b,5a,6b-Cholestanetriol)

Not Available

3D PDB for HMDB0003990 (3b,5a,6b-Cholestanetriol)

Not Available

SMILES for HMDB0003990 (3b,5a,6b-Cholestanetriol)

Not Available

INCHI for HMDB0003990 (3b,5a,6b-Cholestanetriol)

Not Available
View in JSmolView Stereo Labels
SynonymsNot Available
Chemical FormulaC27H48O3
Average Molecular Weight420.6682
Monoisotopic Molecular Weight420.360345402
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number1253-84-5
SMILESNot Available
InChI Identifier
InChI=1S/C27H48O3/c1-17(2)7-6-8-18(3)21-9-10-22-20-15-24(29)27(30)16-19(28)11-14-26(27,5)23(20)12-13-25(21,22)4/h17-24,28-30H,6-16H2,1-5H3/t18-,19+,20+,21-,22+,23+,24-,25-,26-,27+/m1/s1
InChI KeyYMMFNKXZULYSOQ-RUXQDQFYSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Physiological effect
Health effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties
Predicted Molecular PropertiesNot Available
Predicted Chromatographic Properties

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. 8.29 minutes32390414
Predicted by Siyang on May 30, 202219.3057 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.56 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid54.0 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid3320.5 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid346.4 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid248.7 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid182.0 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid603.9 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid1074.3 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid859.5 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)95.7 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1580.3 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid648.9 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid2016.5 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid536.7 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid536.7 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate181.0 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA379.3 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water8.3 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3b,5a,6b-Cholestanetriol[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@@H](O)[C@@]2(O)C[C@@H](O)CC[C@]12C2881.5Standard polar33892256
3b,5a,6b-Cholestanetriol[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@@H](O)[C@@]2(O)C[C@@H](O)CC[C@]12C3387.0Standard non polar33892256
3b,5a,6b-Cholestanetriol[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@@H](O)[C@@]2(O)C[C@@H](O)CC[C@]12C3588.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3b,5a,6b-Cholestanetriol,1TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O[Si](C)(C)C)[C@@]4(O)C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3352.5Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,1TMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O)[C@@]4(O[Si](C)(C)C)C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3308.0Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,1TMS,isomer #3CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O)[C@@]4(O)C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3347.1Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,2TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O[Si](C)(C)C)[C@@]4(O[Si](C)(C)C)C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3269.8Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,2TMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O[Si](C)(C)C)[C@@]4(O)C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3286.0Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,2TMS,isomer #3CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O)[C@@]4(O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3247.2Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,3TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O[Si](C)(C)C)[C@@]4(O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3257.3Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,1TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@]4(O)C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3595.6Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,1TBDMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O)[C@@]4(O[Si](C)(C)C(C)(C)C)C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3537.2Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,1TBDMS,isomer #3CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O)[C@@]4(O)C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3608.8Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,2TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@]4(O[Si](C)(C)C(C)(C)C)C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3715.0Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,2TBDMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@]4(O)C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3774.5Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,2TBDMS,isomer #3CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O)[C@@]4(O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3718.8Semi standard non polar33892256
3b,5a,6b-Cholestanetriol,3TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@]4(O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3921.8Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothInflammatory bowel disease details
Associated Disorders and Diseases
Disease References
Inflammatory bowel disease
  1. Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Associated OMIM IDsNone
External LinksNot Available
References
Synthesis ReferenceFieser, Louis F.; Rajagopalan, Srinivasa. Selective oxidation with N-bromosuccinimide. II. Cholestane-3b,5a,6b-triol. Journal of the American Chemical Society (1949), 71 3938-41.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bjorkhem I, Breuer O, Angelin B, Wikstrom SA: Assay of unesterified cholesterol-5,6-epoxide in human serum by isotope dilution mass spectrometry. Levels in the healthy state and in hyperlipoproteinemia. J Lipid Res. 1988 Aug;29(8):1031-8. [PubMed:3183516 ]