Np mrd loader

Record Information
Version2.0
Created at2024-09-11 20:25:11 UTC
Updated at2024-09-11 20:25:11 UTC
NP-MRD IDNP0339208
Secondary Accession NumbersNone
Natural Product Identification
Common Name3a,7b,21-Trihydroxy-5b-cholanoic acid
Description3A,7b,21-Trihydroxy-5b-cholanoic acid, also known as 21-hydroxyisocholate or lagocholate, belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an nterohepatic circuit. 3A,7b,21-Trihydroxy-5b-cholanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are steroid acids found predominantly in bile of mammals. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. 3A,7b,21-Trihydroxy-5b-cholanoic acid is a bile acid.
Structure
Thumb
Synonyms
ValueSource
3a,7b,21-Trihydroxy-5b-cholanoateGenerator
21-HydroxyisocholateHMDB
21-Hydroxyisocholic acidHMDB
3a,7a,21-Trihydroxy-5b-cholanateHMDB
3a,7a,21-Trihydroxy-5b-cholanic acidHMDB
3a,7a,21-Trihydroxy-5b-cholanoateHMDB
3a,7a,21-Trihydroxy-5b-cholanoic acidHMDB
LagocholateHMDB
Lagocholic acidHMDB
(5S)-5-[(2S,5R,9S,15S)-5,9-Dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-4,5-dihydroxypentanoateGenerator
Chemical FormulaC24H40O6
Average Mass424.5708 Da
Monoisotopic Mass424.28249 Da
IUPAC Name(5S)-5-[(2S,5R,9S,15S)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-4,5-dihydroxypentanoic acid
Traditional Name(5S)-5-[(2S,5R,9S,15S)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-4,5-dihydroxypentanoic acid
CAS Registry NumberNot Available
SMILES
C[C@]12CCC3C(C1CCC2[C@H](O)C(O)CCC(O)=O)[C@@H](O)CC1C[C@H](O)CC[C@]31C
InChI Identifier
InChI=1S/C24H40O6/c1-23-9-7-14(25)11-13(23)12-19(27)21-15-3-4-17(24(15,2)10-8-16(21)23)22(30)18(26)5-6-20(28)29/h13-19,21-22,25-27,30H,3-12H2,1-2H3,(H,28,29)/t13?,14-,15?,16?,17?,18?,19+,21?,22+,23+,24+/m1/s1
InChI KeyJHBLUEHIRYMJOU-ZSFPCQDKSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • 20-hydroxysteroid
  • Androgen-skeleton
  • 3-hydroxysteroid
  • 7-hydroxysteroid
  • 7-alpha-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acyl
  • Fatty acid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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
logP1.46ALOGPS
logP1.49ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)4.48ChemAxon
pKa (Strongest Basic)-0.54ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area118.22 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity112.28 m³·mol⁻¹ChemAxon
Polarizability48.45 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0013192
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029325
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481646
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References