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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:45:36 UTC
HMDB IDHMDB0000483
Secondary Accession Numbers
  • HMDB00483
Metabolite Identification
Common Name5b-Cholestane-3a,7a,12a,23S,25-pentol
Description5b-Cholestane-3a,7a,12a,23S,25-pentol belongs to the class of organic compounds known as pentahydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing five hydroxyl groups. 5b-Cholestane-3a,7a,12a,23S,25-pentol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582752134
Synonyms
ValueSource
(23S)-5b-Cholestane-3a,7a,12a,23,25-pentolHMDB
(3alpha,5beta,7alpha,12alpha,23S)-Cholestane-3,7,12,23,25-pentolHMDB
Chemical FormulaC27H48O5
Average Molecular Weight452.667
Monoisotopic Molecular Weight452.350174646
IUPAC Name(1S,2S,5R,7S,9R,10R,15R,16S)-14-[(2S,4S)-4,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol
Traditional Name(1S,2S,5R,7S,9R,10R,15R,16S)-14-[(2S,4S)-4,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol
CAS Registry Number59906-15-9
SMILES
[H]C1CC([C@@H](C)C[C@H](O)CC(C)(C)O)[C@]2(C)C1[C@]1([H])[C@H](O)C[C@]3([H])C[C@H](O)CC[C@]3(C)[C@@]1([H])C[C@@H]2O
InChI Identifier
InChI=1S/C27H48O5/c1-15(10-18(29)14-25(2,3)32)19-6-7-20-24-21(13-23(31)27(19,20)5)26(4)9-8-17(28)11-16(26)12-22(24)30/h15-24,28-32H,6-14H2,1-5H3/t15-,16-,17+,18-,19?,20?,21-,22+,23-,24-,26-,27+/m0/s1
InChI KeyOXSBBBPDYVCAKC-CTSLUMRNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pentahydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing five hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentPentahydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Cholesterol
  • Cholesterol-skeleton
  • Pentahydroxy bile acid, alcohol, or derivatives
  • Cholestane-skeleton
  • 25-hydroxysteroid
  • 23-hydroxysteroid
  • 3-hydroxysteroid
  • 7-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 12-hydroxysteroid
  • Hydroxysteroid
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

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 Solubility0.052 g/LALOGPS
logP10(2.33) g/LALOGPS
logP10(2.05) g/LChemAxon
logS10(-3.9) g/LALOGPS
pKa (Strongest Acidic)14.93ChemAxon
pKa (Strongest Basic)-0.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area101.15 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity126.34 m³·mol⁻¹ChemAxon
Polarizability53.41 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+204.94631661259
DarkChem[M-H]-200.09331661259
AllCCS[M+H]+213.58732859911
AllCCS[M-H]-209.11332859911
DeepCCS[M+H]+213.67430932474
DeepCCS[M-H]-211.84930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5b-Cholestane-3a,7a,12a,23S,25-pentol[H]C1CC([C@@H](C)C[C@H](O)CC(C)(C)O)[C@]2(C)C1[C@]1([H])[C@H](O)C[C@]3([H])C[C@H](O)CC[C@]3(C)[C@@]1([H])C[C@@H]2O3172.9Standard polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol[H]C1CC([C@@H](C)C[C@H](O)CC(C)(C)O)[C@]2(C)C1[C@]1([H])[C@H](O)C[C@]3([H])C[C@H](O)CC[C@]3(C)[C@@]1([H])C[C@@H]2O3545.3Standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol[H]C1CC([C@@H](C)C[C@H](O)CC(C)(C)O)[C@]2(C)C1[C@]1([H])[C@H](O)C[C@]3([H])C[C@H](O)CC[C@]3(C)[C@@]1([H])C[C@@H]2O3875.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5b-Cholestane-3a,7a,12a,23S,25-pentol,1TMS,isomer #1C[C@@H](C[C@@H](CC(C)(C)O)O[Si](C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O)[C@]12C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O3664.1Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,1TMS,isomer #2C[C@@H](C[C@H](O)CC(C)(C)O[Si](C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O)[C@]12C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O3753.6Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,1TMS,isomer #3C[C@@H](C[C@H](O)CC(C)(C)O)C1CCC2[C@H]3[C@H](C[C@H](O)[C@]12C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C3625.8Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,1TMS,isomer #4C[C@@H](C[C@H](O)CC(C)(C)O)C1CCC2[C@H]3[C@H](C[C@H](O)[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O3715.2Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,1TMS,isomer #5C[C@@H](C[C@H](O)CC(C)(C)O)C1CCC2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@]12C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O3656.2Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,2TMS,isomer #1C[C@@H](C[C@@H](CC(C)(C)O[Si](C)(C)C)O[Si](C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O)[C@]12C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O3752.1Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,2TMS,isomer #10C[C@@H](C[C@H](O)CC(C)(C)O)C1CCC2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O3611.0Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,2TMS,isomer #2C[C@@H](C[C@@H](CC(C)(C)O)O[Si](C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@]12C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O3572.0Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,2TMS,isomer #3C[C@@H](C[C@@H](CC(C)(C)O)O[Si](C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O)[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O3641.4Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,2TMS,isomer #4C[C@@H](C[C@@H](CC(C)(C)O)O[Si](C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O)[C@]12C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C3522.5Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,2TMS,isomer #5C[C@@H](C[C@H](O)CC(C)(C)O[Si](C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@]12C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O3693.2Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,2TMS,isomer #6C[C@@H](C[C@H](O)CC(C)(C)O[Si](C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O)[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O3765.8Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,2TMS,isomer #7C[C@@H](C[C@H](O)CC(C)(C)O[Si](C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O)[C@]12C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C3657.7Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,2TMS,isomer #8C[C@@H](C[C@H](O)CC(C)(C)O)C1CCC2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@]12C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C3542.3Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,2TMS,isomer #9C[C@@H](C[C@H](O)CC(C)(C)O)C1CCC2[C@H]3[C@H](C[C@H](O)[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C3586.4Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,3TMS,isomer #1C[C@@H](C[C@@H](CC(C)(C)O[Si](C)(C)C)O[Si](C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@]12C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O3697.2Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,3TMS,isomer #10C[C@@H](C[C@H](O)CC(C)(C)O)C1CCC2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C3521.5Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,3TMS,isomer #2C[C@@H](C[C@@H](CC(C)(C)O[Si](C)(C)C)O[Si](C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O)[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O3746.0Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,3TMS,isomer #3C[C@@H](C[C@@H](CC(C)(C)O[Si](C)(C)C)O[Si](C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O)[C@]12C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C3639.5Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,3TMS,isomer #4C[C@@H](C[C@@H](CC(C)(C)O)O[Si](C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O3523.2Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,3TMS,isomer #5C[C@@H](C[C@@H](CC(C)(C)O)O[Si](C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@]12C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C3468.3Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,3TMS,isomer #6C[C@@H](C[C@@H](CC(C)(C)O)O[Si](C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O)[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C3493.2Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,3TMS,isomer #7C[C@@H](C[C@H](O)CC(C)(C)O[Si](C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O3668.9Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,3TMS,isomer #8C[C@@H](C[C@H](O)CC(C)(C)O[Si](C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@]12C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C3604.2Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,3TMS,isomer #9C[C@@H](C[C@H](O)CC(C)(C)O[Si](C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O)[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C3631.9Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,4TMS,isomer #1C[C@@H](C[C@@H](CC(C)(C)O[Si](C)(C)C)O[Si](C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O3660.2Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,4TMS,isomer #2C[C@@H](C[C@@H](CC(C)(C)O[Si](C)(C)C)O[Si](C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@]12C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C3615.9Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,4TMS,isomer #3C[C@@H](C[C@@H](CC(C)(C)O[Si](C)(C)C)O[Si](C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O)[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C3632.3Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,4TMS,isomer #4C[C@@H](C[C@@H](CC(C)(C)O)O[Si](C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C3448.6Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,4TMS,isomer #5C[C@@H](C[C@H](O)CC(C)(C)O[Si](C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C3594.0Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,5TMS,isomer #1C[C@@H](C[C@@H](CC(C)(C)O[Si](C)(C)C)O[Si](C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C3610.4Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,1TBDMS,isomer #1C[C@@H](C[C@@H](CC(C)(C)O)O[Si](C)(C)C(C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O)[C@]12C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O3896.3Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,1TBDMS,isomer #2C[C@@H](C[C@H](O)CC(C)(C)O[Si](C)(C)C(C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O)[C@]12C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O3983.6Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,1TBDMS,isomer #3C[C@@H](C[C@H](O)CC(C)(C)O)C1CCC2[C@H]3[C@H](C[C@H](O)[C@]12C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C3828.9Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,1TBDMS,isomer #4C[C@@H](C[C@H](O)CC(C)(C)O)C1CCC2[C@H]3[C@H](C[C@H](O)[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O3928.8Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,1TBDMS,isomer #5C[C@@H](C[C@H](O)CC(C)(C)O)C1CCC2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@]12C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O3874.6Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,2TBDMS,isomer #1C[C@@H](C[C@@H](CC(C)(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O)[C@]12C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O4215.1Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,2TBDMS,isomer #10C[C@@H](C[C@H](O)CC(C)(C)O)C1CCC2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O4045.5Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,2TBDMS,isomer #2C[C@@H](C[C@@H](CC(C)(C)O)O[Si](C)(C)C(C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@]12C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O4054.3Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,2TBDMS,isomer #3C[C@@H](C[C@@H](CC(C)(C)O)O[Si](C)(C)C(C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O)[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O4108.5Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,2TBDMS,isomer #4C[C@@H](C[C@@H](CC(C)(C)O)O[Si](C)(C)C(C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O)[C@]12C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C3984.5Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,2TBDMS,isomer #5C[C@@H](C[C@H](O)CC(C)(C)O[Si](C)(C)C(C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@]12C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O4155.4Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,2TBDMS,isomer #6C[C@@H](C[C@H](O)CC(C)(C)O[Si](C)(C)C(C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O)[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O4217.3Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,2TBDMS,isomer #7C[C@@H](C[C@H](O)CC(C)(C)O[Si](C)(C)C(C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O)[C@]12C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C4087.6Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,2TBDMS,isomer #8C[C@@H](C[C@H](O)CC(C)(C)O)C1CCC2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@]12C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C3974.4Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,2TBDMS,isomer #9C[C@@H](C[C@H](O)CC(C)(C)O)C1CCC2[C@H]3[C@H](C[C@H](O)[C@]12C)[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)C4000.4Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,3TBDMS,isomer #1C[C@@H](C[C@@H](CC(C)(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@]12C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O4383.6Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,3TBDMS,isomer #10C[C@@H](C[C@H](O)CC(C)(C)O)C1CCC2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@]12C)[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)C4145.5Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,3TBDMS,isomer #2C[C@@H](C[C@@H](CC(C)(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O)[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O4412.1Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,3TBDMS,isomer #3C[C@@H](C[C@@H](CC(C)(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O)[C@]12C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C4286.8Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,3TBDMS,isomer #4C[C@@H](C[C@@H](CC(C)(C)O)O[Si](C)(C)C(C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O4227.8Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,3TBDMS,isomer #5C[C@@H](C[C@@H](CC(C)(C)O)O[Si](C)(C)C(C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@]12C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C4136.9Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,3TBDMS,isomer #6C[C@@H](C[C@@H](CC(C)(C)O)O[Si](C)(C)C(C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O)[C@]12C)[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)C4162.3Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,3TBDMS,isomer #7C[C@@H](C[C@H](O)CC(C)(C)O[Si](C)(C)C(C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O4336.0Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,3TBDMS,isomer #8C[C@@H](C[C@H](O)CC(C)(C)O[Si](C)(C)C(C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@]12C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C4242.5Semi standard non polar33892256
5b-Cholestane-3a,7a,12a,23S,25-pentol,3TBDMS,isomer #9C[C@@H](C[C@H](O)CC(C)(C)O[Si](C)(C)C(C)(C)C)C1CCC2[C@H]3[C@H](C[C@H](O)[C@]12C)[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)C4263.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-3324900000-ce081905e393e80511e02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol GC-MS (3 TMS) - 70eV, Positivesplash10-0udi-1221019000-7bbdaca94cf9b39898632017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol GC-MS (TMS_3_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol GC-MS (TMS_3_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol GC-MS (TMS_3_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol GC-MS (TMS_3_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol GC-MS (TMS_3_6) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol GC-MS (TMS_3_7) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol GC-MS (TMS_3_8) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol 10V, Positive-QTOFsplash10-014r-0000900000-ef4a2790d00f39151d5b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol 20V, Positive-QTOFsplash10-014i-2005900000-a3c8abf978fcc74e3e282017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol 40V, Positive-QTOFsplash10-07vi-4209700000-0530fc30e51b3d5bdd052017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol 10V, Negative-QTOFsplash10-0ue9-0002900000-33ffd4c8b139bf7602262017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol 20V, Negative-QTOFsplash10-0089-3004900000-c80999c8f40ac84967fb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol 40V, Negative-QTOFsplash10-00di-9002000000-142d4259a51c5ae1ddec2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol 10V, Positive-QTOFsplash10-0i2i-0005900000-7d875b303276a1615a222021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol 20V, Positive-QTOFsplash10-00kr-2296400000-ea9faed6f654b1accab32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol 40V, Positive-QTOFsplash10-0adj-5910000000-3b16ef62f8c409dc0e292021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol 10V, Negative-QTOFsplash10-0udi-0000900000-c21c302202f1722a38412021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol 20V, Negative-QTOFsplash10-0ugi-0003900000-abb573ddd7cf856c85462021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5b-Cholestane-3a,7a,12a,23S,25-pentol 40V, Negative-QTOFsplash10-0kus-1003900000-0cf26722776682cd88a12021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
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
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022068
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5470
PubChem Compound53477695
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceHoshita, Takahiko; Yasuhara, Misao; Kihira, Kenji; Kuramoto, Taiju. Comparative biochemical studies of bile acids and bile alcohols. V. Identification of (23S)-5a-cholestane-3a,7a,12a,23,25-pentol in cerebrotendinous xanthomatosis. Steroids (1976), 27(5), 657-64.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kihira K, Kubota A, Hoshita T: Absolute configuration at carbon 23 of 5 beta-cholestane-3 alpha,7 alpha,12 alpha,23,25-pentol excreted by patients with cerebrotendinous xanthomatosis. J Lipid Res. 1984 Aug;25(8):871-5. [PubMed:6491531 ]
  2. Une M, Harada J, Mikami T, Hoshita T: High-performance liquid chromatographic separation of ultraviolet-absorbing bile alcohol derivatives. J Chromatogr B Biomed Appl. 1996 Jun 28;682(1):157-61. [PubMed:8832436 ]
  3. Shimazu K, Kuwabara M, Yoshii M, Kihira K, Takeuchi H, Nakano I, Ozawa S, Onuki M, Hatta Y, Hoshita T: Bile alcohol profiles in bile, urine, and feces of a patient with cerebrotendinous xanthomatosis. J Biochem. 1986 Feb;99(2):477-83. [PubMed:3700361 ]
  4. Kosaka D, Hiraoka T, Kohoda T, Kajiyama G, Yamauchi T, Kihira K, Kuramoto T, Hoshita T: Stable isotope dilution assay for 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol and 5 beta-cholestane-3 alpha,7 alpha,12 alpha,23,25-pentol in human serum using [26,27-D6] labeled internal standards; a highly accurate approach to the serological diagnosis of cerebrotendinous xanthomatosis. Clin Chim Acta. 1991 May 31;199(1):83-9. [PubMed:1934504 ]