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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:55 UTC
Update Date2022-03-07 02:49:16 UTC
HMDB IDHMDB0002504
Secondary Accession Numbers
  • HMDB02504
Metabolite Identification
Common Name3-Sulfodeoxycholic acid
DescriptionDeoxycholic Acid/analogs and derivatives.
Structure
Data?1582752251
SynonymsNot Available
Chemical FormulaC23H38O7S
Average Molecular Weight458.609
Monoisotopic Molecular Weight458.23382426
IUPAC Name(4R)-4-[(1S,2S,5R,7R,10S,11S,14R,16S)-16-hydroxy-2-methyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
Traditional Name(4R)-4-[(1S,2S,5R,7R,10S,11S,14R,16S)-16-hydroxy-2-methyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
CAS Registry Number67030-48-2
SMILES
[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)C1[C@@H](O)C[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@@H](CC[C@]12C)OS(O)(=O)=O
InChI Identifier
InChI=1S/C23H38O7S/c1-13(3-8-21(25)26)16-6-7-18-17-5-4-14-11-15(30-31(27,28)29)9-10-23(14,2)19(17)12-20(24)22(16)18/h13-20,22,24H,3-12H2,1-2H3,(H,25,26)(H,27,28,29)/t13-,14-,15-,16-,17+,18+,19+,20+,22?,23+/m1/s1
InChI KeyWSBVSABEAXNERB-JNLBVXOESA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
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 Solubility0.0068 g/LALOGPS
logP0.25ALOGPS
logP1.98ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)-1.5ChemAxon
pKa (Strongest Basic)-0.59ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area121.13 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity114.79 m³·mol⁻¹ChemAxon
Polarizability50.14 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+202.37431661259
DarkChem[M-H]-197.01231661259
DeepCCS[M-2H]-255.91430932474
DeepCCS[M+Na]+229.68630932474
AllCCS[M+H]+209.732859911
AllCCS[M+H-H2O]+208.032859911
AllCCS[M+NH4]+211.432859911
AllCCS[M+Na]+211.832859911
AllCCS[M-H]-205.232859911
AllCCS[M+Na-2H]-206.932859911
AllCCS[M+HCOO]-208.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Sulfodeoxycholic acid[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)C1[C@@H](O)C[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@@H](CC[C@]12C)OS(O)(=O)=O5145.7Standard polar33892256
3-Sulfodeoxycholic acid[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)C1[C@@H](O)C[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@@H](CC[C@]12C)OS(O)(=O)=O3532.1Standard non polar33892256
3-Sulfodeoxycholic acid[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)C1[C@@H](O)C[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@@H](CC[C@]12C)OS(O)(=O)=O3906.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Sulfodeoxycholic acid,1TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@@H]2C1[C@@H](O)C[C@H]1[C@H]2CC[C@@H]2C[C@H](OS(=O)(=O)O)CC[C@]12C3694.7Semi standard non polar33892256
3-Sulfodeoxycholic acid,1TMS,isomer #2C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2C1[C@@H](O[Si](C)(C)C)C[C@H]1[C@H]2CC[C@@H]2C[C@H](OS(=O)(=O)O)CC[C@]12C3659.9Semi standard non polar33892256
3-Sulfodeoxycholic acid,1TMS,isomer #3C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2C1[C@@H](O)C[C@H]1[C@H]2CC[C@@H]2C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]12C3723.3Semi standard non polar33892256
3-Sulfodeoxycholic acid,2TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@@H]2C1[C@@H](O[Si](C)(C)C)C[C@H]1[C@H]2CC[C@@H]2C[C@H](OS(=O)(=O)O)CC[C@]12C3650.1Semi standard non polar33892256
3-Sulfodeoxycholic acid,2TMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@@H]2C1[C@@H](O)C[C@H]1[C@H]2CC[C@@H]2C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]12C3702.8Semi standard non polar33892256
3-Sulfodeoxycholic acid,2TMS,isomer #3C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2C1[C@@H](O[Si](C)(C)C)C[C@H]1[C@H]2CC[C@@H]2C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]12C3678.5Semi standard non polar33892256
3-Sulfodeoxycholic acid,3TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@@H]2C1[C@@H](O[Si](C)(C)C)C[C@H]1[C@H]2CC[C@@H]2C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]12C3658.8Semi standard non polar33892256
3-Sulfodeoxycholic acid,3TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@@H]2C1[C@@H](O[Si](C)(C)C)C[C@H]1[C@H]2CC[C@@H]2C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]12C4040.4Standard non polar33892256
3-Sulfodeoxycholic acid,3TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@@H]2C1[C@@H](O[Si](C)(C)C)C[C@H]1[C@H]2CC[C@@H]2C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]12C4455.5Standard polar33892256
3-Sulfodeoxycholic acid,1TBDMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@@H]2C1[C@@H](O)C[C@H]1[C@H]2CC[C@@H]2C[C@H](OS(=O)(=O)O)CC[C@]12C3976.3Semi standard non polar33892256
3-Sulfodeoxycholic acid,1TBDMS,isomer #2C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1[C@H]2CC[C@@H]2C[C@H](OS(=O)(=O)O)CC[C@]12C3898.5Semi standard non polar33892256
3-Sulfodeoxycholic acid,1TBDMS,isomer #3C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2C1[C@@H](O)C[C@H]1[C@H]2CC[C@@H]2C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]12C3926.9Semi standard non polar33892256
3-Sulfodeoxycholic acid,2TBDMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@@H]2C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1[C@H]2CC[C@@H]2C[C@H](OS(=O)(=O)O)CC[C@]12C4159.3Semi standard non polar33892256
3-Sulfodeoxycholic acid,2TBDMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@@H]2C1[C@@H](O)C[C@H]1[C@H]2CC[C@@H]2C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]12C4168.7Semi standard non polar33892256
3-Sulfodeoxycholic acid,2TBDMS,isomer #3C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1[C@H]2CC[C@@H]2C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]12C4098.0Semi standard non polar33892256
3-Sulfodeoxycholic acid,3TBDMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@@H]2C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1[C@H]2CC[C@@H]2C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]12C4321.1Semi standard non polar33892256
3-Sulfodeoxycholic acid,3TBDMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@@H]2C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1[C@H]2CC[C@@H]2C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]12C4884.1Standard non polar33892256
3-Sulfodeoxycholic acid,3TBDMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@@H]2C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1[C@H]2CC[C@@H]2C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]12C4564.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sulfodeoxycholic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-002v-0658900000-0a33233e6e2577e6f7892017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sulfodeoxycholic acid GC-MS (2 TMS) - 70eV, Positivesplash10-000i-1122390000-ae7bf852c15966093e7a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Sulfodeoxycholic acid 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 - 3-Sulfodeoxycholic acid 10V, Positive-QTOFsplash10-052f-0003900000-cbad9c4fb9b8f1cbb6fe2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sulfodeoxycholic acid 20V, Positive-QTOFsplash10-01ox-0009200000-772c27f4890fa72bcedf2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sulfodeoxycholic acid 40V, Positive-QTOFsplash10-014i-6279100000-40edc0c407a59d2c34842016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sulfodeoxycholic acid 10V, Negative-QTOFsplash10-0a4i-0002900000-2e4bf8aa360c146ba8672016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sulfodeoxycholic acid 20V, Negative-QTOFsplash10-0a4i-2009300000-628af0b8dba3dd0b35532016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sulfodeoxycholic acid 40V, Negative-QTOFsplash10-0a59-9006000000-71659c7f06a5bd42f29a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sulfodeoxycholic acid 10V, Positive-QTOFsplash10-0a4l-0002900000-f9c35a7e97e02bbaab4f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sulfodeoxycholic acid 20V, Positive-QTOFsplash10-0006-0039100000-3bfcdd4ad74a20385baa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sulfodeoxycholic acid 40V, Positive-QTOFsplash10-0a4i-9266000000-16c5139e4c5f6550f43e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sulfodeoxycholic acid 10V, Negative-QTOFsplash10-0a4r-0000900000-0038f7a5f904434d71932021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sulfodeoxycholic acid 20V, Negative-QTOFsplash10-0a4i-1000900000-0fa1bf20eab8eb533c4a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Sulfodeoxycholic acid 40V, Negative-QTOFsplash10-052k-6009200000-47875fa725f07833a1c72021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified9.36 +/- 15.51 nmol/g dry fecesNot SpecifiedNot Specified
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
External LinksNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in binding
Specific function:
Ileal protein which stimulates gastric acid and pepsinogen secretion. Seems to be able to bind to bile salts and bilirubins. Isoform 2 is essential for the survival of colon cancer cells to bile acid-induced apoptosis
Gene Name:
FABP6
Uniprot ID:
P51161
Molecular weight:
14371.2
References
  1. Kurz M, Brachvogel V, Matter H, Stengelin S, Thuring H, Kramer W: Insights into the bile acid transportation system: the human ileal lipid-binding protein-cholyltaurine complex and its comparison with homologous structures. Proteins. 2003 Feb 1;50(2):312-28. [PubMed:12486725 ]

Transporters

General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotrexate and sulfobromophthalein (BSP)
Gene Name:
SLCO1B3
Uniprot ID:
Q9NPD5
Molecular weight:
77402.2
General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:
SLCO1B1
Uniprot ID:
Q9Y6L6
Molecular weight:
76448.0
References
  1. Michalski C, Cui Y, Nies AT, Nuessler AK, Neuhaus P, Zanger UM, Klein K, Eichelbaum M, Keppler D, Konig J: A naturally occurring mutation in the SLC21A6 gene causing impaired membrane localization of the hepatocyte uptake transporter. J Biol Chem. 2002 Nov 8;277(45):43058-63. Epub 2002 Aug 23. [PubMed:12196548 ]
General function:
Involved in ATP binding
Specific function:
May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocytes
Gene Name:
ABCC3
Uniprot ID:
O15438
Molecular weight:
169341.1
General function:
Involved in ATP binding
Specific function:
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
Gene Name:
ABCB11
Uniprot ID:
O95342
Molecular weight:
146405.8
General function:
Involved in bile acid:sodium symporter activity
Specific function:
Plays a critical role in the sodium-dependent reabsorption of bile acids from the lumen of the small intestine. Plays a key role in cholesterol metabolism
Gene Name:
SLC10A2
Uniprot ID:
Q12908
Molecular weight:
37697.4
References
  1. Kramer W, Girbig F, Glombik H, Corsiero D, Stengelin S, Weyland C: Identification of a ligand-binding site in the Na+/bile acid cotransporting protein from rabbit ileum. J Biol Chem. 2001 Sep 21;276(38):36020-7. Epub 2001 Jul 10. [PubMed:11447228 ]
General function:
Involved in bile acid:sodium symporter activity
Specific function:
The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presence of sodium.
Gene Name:
SLC10A1
Uniprot ID:
Q14973
Molecular weight:
38118.64
General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
Gene Name:
SLCO1A2
Uniprot ID:
P46721
Molecular weight:
74144.1
General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as the thyroid hormones T3 (triiodo-L-thyronine), T4 (thyroxine) and rT3, and of estrone-3-sulfate and taurocholate
Gene Name:
SLCO4A1
Uniprot ID:
Q96BD0
Molecular weight:
77192.5