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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:05 UTC
HMDB IDHMDB0000659
Secondary Accession Numbers
  • HMDB00659
Metabolite Identification
Common NameDeoxycholic acid disulfate
DescriptionDeoxycholic acid disulfate, also known as deoxycholate disulphate, belongs to the class of organic compounds known as bile acids, alcohols and derivatives. These are organic compounds containing an alcohol or acid derivative of cholic acid. Deoxycholic acid disulfate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1582752147
Synonyms
ValueSource
Deoxycholate disulfateGenerator
Deoxycholate disulphateGenerator
Deoxycholic acid disulfuric acidGenerator
Deoxycholic acid disulphuric acidGenerator
Deoxycholic acid disulphateHMDB
Chemical FormulaC24H40O10S2
Average Molecular Weight552.698
Monoisotopic Molecular Weight552.20628888
IUPAC Name(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-2,15-dimethyl-5,16-bis(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
Traditional Name(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-2,15-dimethyl-5,16-bis(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
CAS Registry Number67030-51-7
SMILES
[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@H](C[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@@H](CC[C@]12C)OS(O)(=O)=O)OS(O)(=O)=O
InChI Identifier
InChI=1S/C24H40O10S2/c1-14(4-9-22(25)26)18-7-8-19-17-6-5-15-12-16(33-35(27,28)29)10-11-23(15,2)20(17)13-21(24(18,19)3)34-36(30,31)32/h14-21H,4-13H2,1-3H3,(H,25,26)(H,27,28,29)(H,30,31,32)/t14-,15-,16-,17+,18-,19+,20+,21+,23+,24-/m1/s1
InChI KeyBYHNMIVTBIJJFZ-LLQZFEROSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bile acids, alcohols and derivatives. These are organic compounds containing an alcohol or acid derivative of cholic acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentBile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Bile acid, alcohol, or derivatives
  • Sulfated steroid skeleton
  • Sulfuric acid monoester
  • Sulfate-ester
  • Alkyl sulfate
  • Sulfuric acid ester
  • Organic sulfuric acid or derivatives
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
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 Solubility0.012 g/LALOGPS
logP-0.74ALOGPS
logP3.9ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)-1.7ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area164.5 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity129.18 m³·mol⁻¹ChemAxon
Polarizability57.33 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+222.31532859911
AllCCS[M-H]-218.25432859911
DeepCCS[M-2H]-256.19630932474
DeepCCS[M+Na]+229.9730932474
AllCCS[M+H]+222.332859911
AllCCS[M+H-H2O]+221.132859911
AllCCS[M+NH4]+223.532859911
AllCCS[M+Na]+223.832859911
AllCCS[M-H]-218.332859911
AllCCS[M+Na-2H]-220.732859911
AllCCS[M+HCOO]-223.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Deoxycholic acid disulfate[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@H](C[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@@H](CC[C@]12C)OS(O)(=O)=O)OS(O)(=O)=O4893.7Standard polar33892256
Deoxycholic acid disulfate[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@H](C[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@@H](CC[C@]12C)OS(O)(=O)=O)OS(O)(=O)=O3861.7Standard non polar33892256
Deoxycholic acid disulfate[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@H](C[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@@H](CC[C@]12C)OS(O)(=O)=O)OS(O)(=O)=O4363.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Deoxycholic acid disulfate,1TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3C[C@H](OS(=O)(=O)O)[C@@]21C4041.1Semi standard non polar33892256
Deoxycholic acid disulfate,1TMS,isomer #2C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](OS(=O)(=O)O)[C@@]21C4088.4Semi standard non polar33892256
Deoxycholic acid disulfate,1TMS,isomer #3C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3C[C@H](OS(=O)(=O)O[Si](C)(C)C)[C@@]21C4103.9Semi standard non polar33892256
Deoxycholic acid disulfate,2TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](OS(=O)(=O)O)[C@@]21C4014.9Semi standard non polar33892256
Deoxycholic acid disulfate,2TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](OS(=O)(=O)O)[C@@]21C4469.3Standard non polar33892256
Deoxycholic acid disulfate,2TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](OS(=O)(=O)O)[C@@]21C5454.4Standard polar33892256
Deoxycholic acid disulfate,2TMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3C[C@H](OS(=O)(=O)O[Si](C)(C)C)[C@@]21C4026.8Semi standard non polar33892256
Deoxycholic acid disulfate,2TMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3C[C@H](OS(=O)(=O)O[Si](C)(C)C)[C@@]21C4460.0Standard non polar33892256
Deoxycholic acid disulfate,2TMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3C[C@H](OS(=O)(=O)O[Si](C)(C)C)[C@@]21C5505.2Standard polar33892256
Deoxycholic acid disulfate,2TMS,isomer #3C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](OS(=O)(=O)O[Si](C)(C)C)[C@@]21C4071.1Semi standard non polar33892256
Deoxycholic acid disulfate,2TMS,isomer #3C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](OS(=O)(=O)O[Si](C)(C)C)[C@@]21C4445.7Standard non polar33892256
Deoxycholic acid disulfate,2TMS,isomer #3C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](OS(=O)(=O)O[Si](C)(C)C)[C@@]21C5414.7Standard polar33892256
Deoxycholic acid disulfate,3TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](OS(=O)(=O)O[Si](C)(C)C)[C@@]21C3993.5Semi standard non polar33892256
Deoxycholic acid disulfate,3TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](OS(=O)(=O)O[Si](C)(C)C)[C@@]21C4642.7Standard non polar33892256
Deoxycholic acid disulfate,3TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3C[C@H](OS(=O)(=O)O[Si](C)(C)C)[C@@]21C5259.2Standard polar33892256
Deoxycholic acid disulfate,1TBDMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3C[C@H](OS(=O)(=O)O)[C@@]21C4314.0Semi standard non polar33892256
Deoxycholic acid disulfate,1TBDMS,isomer #2C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](OS(=O)(=O)O)[C@@]21C4309.4Semi standard non polar33892256
Deoxycholic acid disulfate,1TBDMS,isomer #3C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@]21C4305.2Semi standard non polar33892256
Deoxycholic acid disulfate,2TBDMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](OS(=O)(=O)O)[C@@]21C4511.8Semi standard non polar33892256
Deoxycholic acid disulfate,2TBDMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](OS(=O)(=O)O)[C@@]21C5081.3Standard non polar33892256
Deoxycholic acid disulfate,2TBDMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](OS(=O)(=O)O)[C@@]21C5503.7Standard polar33892256
Deoxycholic acid disulfate,2TBDMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@]21C4505.7Semi standard non polar33892256
Deoxycholic acid disulfate,2TBDMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@]21C5061.7Standard non polar33892256
Deoxycholic acid disulfate,2TBDMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@]21C5548.2Standard polar33892256
Deoxycholic acid disulfate,2TBDMS,isomer #3C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@]21C4513.1Semi standard non polar33892256
Deoxycholic acid disulfate,2TBDMS,isomer #3C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@]21C5054.3Standard non polar33892256
Deoxycholic acid disulfate,2TBDMS,isomer #3C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@]21C5467.0Standard polar33892256
Deoxycholic acid disulfate,3TBDMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@]21C4677.5Semi standard non polar33892256
Deoxycholic acid disulfate,3TBDMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@]21C5515.9Standard non polar33892256
Deoxycholic acid disulfate,3TBDMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@]21C5298.1Standard polar33892256
Spectra
Biological Properties
Cellular Locations
  • Extracellular
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 IDFDB022168
KNApSAcK IDNot Available
Chemspider ID402421
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5630
PubChem Compound457190
PDB IDNot Available
ChEBI ID491276
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceBureeva, Svetlana; Andia-Pravdivy, Julian; Symon, Andrey; Bichucher, Anna; Moskaleva, Vera; Popenko, Vladimir; Shpak, Alexey; Shvets, Vitaly; Kozlov, Leonid; Kaplun, Alexander. Selective inhibition of the interaction of C1q with immunoglobulins and the classical pathway of complement activation by steroids and triterpenoids sulfates. Bioorganic & Medicinal Chemistry (2007), 15(10), 3489-3498.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hoffmann GF, Seppel CK, Holmes B, Mitchell L, Christen HJ, Hanefeld F, Rating D, Nyhan WL: Quantitative organic acid analysis in cerebrospinal fluid and plasma: reference values in a pediatric population. J Chromatogr. 1993 Jul 23;617(1):1-10. [PubMed:8376520 ]

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