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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:39 UTC
Update Date2017-10-23 19:03:57 UTC
HMDB IDHMDB0002163
Secondary Accession Numbers
  • HMDB02163
Metabolite Identification
Common NameTrihydroxycoprostanoic acid
DescriptionTrihydroxycoprostanoic acid is excreted in the urine of patients with Zellweger syndrome (PMID 7347441 ). The oxidation trihydroxycoprostanic acid is deficient in liver homogenates from patients with peroxisomal diseases (PMID 2576087 ).
Structure
Thumb
Synonyms
ValueSource
(3a,5b,7a,12a)-3,7,12-Trihydroxy-cholestane-5-carboxylateHMDB
(3a,5b,7a,12a)-3,7,12-Trihydroxy-cholestane-5-carboxylic acidHMDB
(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholestane-5-carboxylateHMDB
(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholestane-5-carboxylic acidHMDB
3,7,12-TrihydroxycoprostanateHMDB
3,7,12-Trihydroxycoprostanic acidHMDB
3alpha,7alpha,12alpha-TrihydroxycoprostanateHMDB
3alpha,7alpha,12alpha-Trihydroxycoprostanic acidHMDB
5-ThcaHMDB
TrihydroxycoprostanoateHMDB
TryhydroxycoprostanateHMDB
Tryhydroxycoprostanic acidHMDB
3 alpha,7 alpha,12 alpha-Trihydroxy-5 beta-cholestanoic acidMeSH
3 alpha,7 alpha,12 alpha-Trihydroxycoprostanic acidMeSH
Chemical FormulaC28H48O5
Average Molecular Weight464.6777
Monoisotopic Molecular Weight464.350174646
IUPAC Name(1S,2R,5R,7R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-7-carboxylic acid
Traditional Name(1S,2R,5R,7R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-7-carboxylic acid
CAS Registry Number863-39-8
SMILES
[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@@]2(C[C@H](O)CC[C@]12C)C(O)=O
InChI Identifier
InChI=1S/C28H48O5/c1-16(2)7-6-8-17(3)19-9-10-20-24-21(13-23(31)27(19,20)5)26(4)12-11-18(29)14-28(26,25(32)33)15-22(24)30/h16-24,29-31H,6-15H2,1-5H3,(H,32,33)/t17-,18-,19-,20+,21+,22-,23+,24+,26-,27-,28+/m1/s1
InChI KeyJIFNDZCDNLFAKC-YAODFNMUSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cholesterols and derivatives. These are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol
  • Cholesterol-skeleton
  • Steroid acid
  • 3-hydroxysteroid
  • 12-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 7-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Polyol
  • Carboxylic acid derivative
  • Organooxygen compound
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

  Health condition:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

  Tissue and substructures:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    Multicellular process:

Role

Industrial application:

Biological role:

  Molecular messenger:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP3.51ALOGPS
logP4.47ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)4.35ChemAxon
pKa (Strongest Basic)-0.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity129.07 m³·mol⁻¹ChemAxon
Polarizability55.37 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006w-1151900000-9964b763512a2672587eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-3214059000-4094305c0a69ba80bb14View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0000900000-b0a4411cb2684a1a2972View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fba-1101900000-990e05e4698fd587ab83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0avi-8404900000-1b74f95b874b3c97fd32View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dj-0000900000-bad6122da3518cc7d5b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0wmj-0000900000-e2d7732c54b6600adc8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0v00-1002900000-8baa3514da0d45921e79View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Peroxisome
Biofluid Locations
  • Blood
Tissue Location
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
Not Available
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified11.4 +/- 5.2 uMAdult (>18 years old)BothZellweger syndrome details
BloodDetected and Quantified10.9 +/- 14.6 uMNewborn (0-30 days old)BothAdrenoleukodystrophy (ALD) details
Associated Disorders and Diseases
Disease References
Adrenoleukodystrophy
  1. Watkins PA, Chen WW, Harris CJ, Hoefler G, Hoefler S, Blake DC Jr, Balfe A, Kelley RI, Moser AB, Beard ME, et al.: Peroxisomal bifunctional enzyme deficiency. J Clin Invest. 1989 Mar;83(3):771-7. [PubMed:2921319 ]
Peroxisomal biogenesis defect
  1. Watkins PA, Chen WW, Harris CJ, Hoefler G, Hoefler S, Blake DC Jr, Balfe A, Kelley RI, Moser AB, Beard ME, et al.: Peroxisomal bifunctional enzyme deficiency. J Clin Invest. 1989 Mar;83(3):771-7. [PubMed:2921319 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022877
KNApSAcK IDNot Available
Chemspider ID108961
KEGG Compound IDNot Available
BioCyc IDCPD-10552
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6519
PubChem Compound122166
PDB IDNot Available
ChEBI ID89753
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Casteels M, Van Roermund CW, Schepers L, Govaert L, Eyssen HJ, Mannaerts GP, Wanders RJ: Deficient oxidation of trihydroxycoprostanic acid in liver homogenates from patients with peroxisomal diseases. J Inherit Metab Dis. 1989;12(4):415-22. [PubMed:2576087 ]
  2. Wanders RJ, Schutgens RB, Heymans HS: Deficient cholesterol side chain oxidation in patients without peroxisomes (Zellweger syndrome): evidence for the involvement of peroxisomes in bile acid synthesis in man. Clin Chim Acta. 1987 Feb 15;162(3):295-301. [PubMed:3568406 ]
  3. Muller-Hocker J, Bise K, Endres W, Hubner G: [Morphology and diagnosis of Zellweger syndrome. A contribution to combined cytochemical-finestructural identification of peroxisomes in autopsy material and frozen liver tissue with case report]. Virchows Arch A Pathol Anat Histol. 1981;393(1):103-14. [PubMed:7347441 ]

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