Back to Compounds

5b-Cyprinol sulfate (FDB024135)

Record Information
Version1.0
Creation date2011-09-21 00:40:27 UTC
Update date2017-04-03 05:02:17 UTC
Primary IDFDB024135
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name5b-Cyprinol sulfate
Description5b-Cyprinol sulfate 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) [HMDB]
CAS Number14808-79-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.056 g/LALOGPS
logP0.77ALOGPS
logP0.63ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)-1.8ChemAxon
pKa (Strongest Basic)-0.14ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area144.52 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity136.55 m³·mol⁻¹ChemAxon
Polarizability59.39 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC27H48O8S
IUPAC name(3-hydroxy-2-{4-[(2S,5R,9R,15R,16R)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentyl}propoxy)sulfonic acid
InChI IdentifierInChI=1S/C27H48O8S/c1-16(5-4-6-17(14-28)15-35-36(32,33)34)20-7-8-21-25-22(13-24(31)27(20,21)3)26(2)10-9-19(29)11-18(26)12-23(25)30/h16-25,28-31H,4-15H2,1-3H3,(H,32,33,34)/t16?,17?,18?,19-,20?,21?,22?,23-,24-,25?,26+,27-/m1/s1
InChI KeyKAOLEMQCYWHOJQ-UQACNIHJSA-N
Isomeric SMILESCC(CCCC(CO)COS(O)(=O)=O)C1CCC2C3[C@H](O)CC4C[C@H](O)CC[C@]4(C)C3C[C@@H](O)[C@]12C
Average Molecular Weight532.73
Monoisotopic Molecular Weight532.306989202
Classification
Description Belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTetrahydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • 26-hydroxysteroid
  • Tetrahydroxy bile acid, alcohol, or derivatives
  • Sulfated steroid skeleton
  • 3-hydroxysteroid
  • 12-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 7-hydroxysteroid
  • Sulfate-ester
  • Sulfuric acid monoester
  • Alkyl sulfate
  • Sulfuric acid ester
  • Organic sulfuric acid or derivatives
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Organic oxide
  • Primary alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
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-MS5b-Cyprinol sulfate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-029i-0605690000-44926b892b4e13e9249cSpectrum
Predicted GC-MS5b-Cyprinol sulfate, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-1411439000-e7f0ffdef09b39c6a2eaSpectrum
Predicted GC-MS5b-Cyprinol sulfate, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cyprinol sulfate, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cyprinol sulfate, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cyprinol sulfate, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cyprinol sulfate, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cyprinol sulfate, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cyprinol sulfate, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cyprinol sulfate, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cyprinol sulfate, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cyprinol sulfate, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cyprinol sulfate, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cyprinol sulfate, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cyprinol sulfate, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cyprinol sulfate, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cyprinol sulfate, TMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cyprinol sulfate, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cyprinol sulfate, TMS_3_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cyprinol sulfate, TMS_3_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cyprinol sulfate, TMS_3_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cyprinol sulfate, TMS_3_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cyprinol sulfate, TMS_3_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cyprinol sulfate, TMS_3_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5b-Cyprinol sulfate, TMS_3_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0000970000-f15f83c9b0d64d0f1fdc2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0001910000-f7976f7a4ce98042c0c92017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zg1-0106900000-b1876cb2e886561744422017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01q9-0000290000-6d88f15692a49251096f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f89-1000930000-361a1e6cf1038a0cb89e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f8d-9102810000-e80240d64990a2ca3b012017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000090000-2298ab02a1ed5709ddc02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2000290000-0fc4f76b2a3c06f03b622021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001j-9103120000-16fc582b17a46701d4742021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0000940000-030c096bc86987b8102d2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ldj-0418900000-ff0b214f96f890c9ed702021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-2922100000-cbe0b8a0e0806d0dc4662021-09-25View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC05468
Pubchem Compound ID53477904
Pubchem Substance IDNot Available
ChEBI ID2149
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06888
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
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