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Record Information
Version2.0
Created at2022-05-11 16:33:51 UTC
Updated at2022-05-11 16:33:51 UTC
NP-MRD IDNP0086889
Secondary Accession NumbersNone
Natural Product Identification
Common NameTrihydroxycoprostanoic acid
DescriptionTrihydroxycoprostanoic acid, also known as 3,7,12-trihydroxycoprostanate or 5-thca, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Trihydroxycoprostanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, trihydroxycoprostanoic acid is involved in cerebrotendinous xanthomatosis (ctx). Trihydroxycoprostanoic acid is excreted in the urine of patients with Zellweger syndrome (PMID 7347441 ), a genetic disorder. Trihydroxycoprostanoic acid was first documented in 1981 (PMID: 7347441). Trihydroxycoprostanoic acid has been found to be associated with the diseases such as d-bifunctional protein deficiency; also trihydroxycoprostanoic acid has been linked to several inborn metabolic disorders including peroxisomal biogenesis defect and adrenoleukodystrophy (PMID: 3568406).
Structure
Thumb
Synonyms
ValueSource
TrihydroxycoprostanoateGenerator
(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
TryhydroxycoprostanateHMDB
Tryhydroxycoprostanic acidHMDB
3 alpha,7 alpha,12 alpha-Trihydroxy-5 beta-cholestanoic acidHMDB
3 alpha,7 alpha,12 alpha-Trihydroxycoprostanic acidHMDB
(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-carboxylateHMDB
Chemical FormulaC28H48O5
Average Mass464.6777 Da
Monoisotopic Mass464.35017 Da
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 NumberNot Available
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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives 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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.51ALOGPS
logP4.47ChemAxon
logS-4.6ALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDHMDB0002163
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022877
KNApSAcK IDNot Available
Chemspider ID108961
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6519
PubChem Compound122166
PDB IDNot Available
ChEBI ID89753
Good Scents IDNot Available
References
General References
  1. 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. doi: 10.1016/0009-8981(87)90048-9. [PubMed:3568406 ]
  2. 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. doi: 10.1007/BF00430874. [PubMed:7347441 ]