Obeticholic acid

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Obeticholic acid are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Obeticholic acid?

The molecule Obeticholic acid presents a molecular formula of C26H44O4 and its IUPAC name is (4R)-4-[(3R,5S,6R,7R,8S,9S,10S,13R,14S,17R)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid.

Obeticholic acid (OBA) is a naturally occurring bile acid that is structurally similar to cholic acid. OBA is produced in the liver and is secreted into the bile. It plays an important role in the absorption of fats and fat-soluble vitamins from the intestine..

OBA is being investigated as a treatment for a variety of liver diseases, including primary biliary cholangitis (PBC), non-alcoholic fatty liver disease (NAFLD), and primary sclerosing cholangitis (PSC). PBC is a chronic liver disease that affects the bile ducts. NAFLD is a condition in which fat accumulates in the liver, and PSC is a chronic inflammatory disease of the bile ducts..

OBA is thought to work by binding to the farnesoid X receptor (FXR), a nuclear receptor that regulates bile acid and lipid metabolism. FXR is expressed in the liver, intestine, and kidney. By binding to FXR, OBA regulates the production and secretion of bile acids and other lipids, and affects the metabolism of glucose and lipid..

OBA is being studied in clinical trials for the treatment of PBC, NAFLD, and PSC. The safety and efficacy of OBA in humans is not yet known..

Please consult your healthcare provider before taking any medication, supplement, or herb..

3D structure

Cartesian coordinates

Geometry of Obeticholic acid in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Obeticholic acid ZXERDUOLZKYMJM-ZWECCWDJSA-N chemical compound 2D structure molecule svg
Obeticholic acid

 

Molecule descriptors

 
IUPAC name(4R)-4-[(3R,5S,6R,7R,8S,9S,10S,13R,14S,17R)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
InChI codeInChI=1S/C26H44O4/c1-5-17-21-14-16(27)10-12-26(21,4)20-11-13-25(3)18(15(2)6-9-22(28)29)7-8-19(25)23(20)24(17)30/h15-21,23-24,27,30H,5-14H2,1-4H3,(H,28,29)/t15-,16-,17-,18-,19+,20+,21+,23+,24-,25-,26-/m1/s1
InChI KeyZXERDUOLZKYMJM-ZWECCWDJSA-N
SMILESCC[C@@H]1[C@@H]2C[C@H](O)CC[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC[C@@H]3[C@H](C)CCC(=O)O)[C@@H]2[C@@H]1O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (3.ALPHA.,5.BETA.,6.ALPHA.,7.ALPHA.)-6-ETHYL-3,7-DIHYDROXYCHOLAN-24-OIC ACID
  • (3alpha,5beta,6alpha,7alpha)-6-Ethyl-3,7-dihydroxycholan-24-oic acid
  • (3alpha,5beta,6alpha,7alpha,8xi)-6-Ethyl-3,7-dihydroxycholan-24-oic acid
  • (3beta,5beta,6alpha,7beta)-6-ethyl-3,7-dihydroxycholan-24-oic acid
  • (4R)-4-[(1S,2S,5R,7S,8R,9R,10S,11S,14R,15R)-8-ethyl-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
  • (4R)-4-[(3R,5S,6R,7R,8S,9S,10S,13R,14S,17R)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
  • (R)-4-((3R,5S,6R,7R,8S,9S,10S,13R,14S,17R)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid
  • (R)-4-((3R,7R,8S,9S,10S,13R,14S,17R)-6-Ethyl-3,7-dihydroxy-10,13-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid
  • 0462Z4S4OZ
  • 1osv
  • 3A, 7A -DIHYDROXY-6A -ETHYL-5B-CHOLAN-24-OIC ACID
  • 3alpha,7alpha-dihydroxy-6alpha-ethyl-5beta-cholan-24-oic acid
  • 459789-99-2
  • 6-ECDCA
  • 6-ECDCA; Obeticholic acid
  • 6-ETHYL-CHENODEOXYCHOLIC ACID
  • 6-Et CDCA
  • 6-Ethyl-CDCA
  • 6-Ethylchenodeoxycholic acid
  • 6-alpha-ethylchenodeoxycholic acid
  • 6-ethyl-3,7-dihydroxycholan-24-oic acid
  • 6ECDCA
  • 6alpha-Ethyl-chenodeoxycholic acid
  • 6alpha-ethyl-3alpha,7alpha-dihydroxy-5beta-cholan-24-oic acid
  • 6alpha-ethylchenodeoxycholic acid
  • A854341
  • AMY16595
  • BDBM21675
  • CS-3813
  • CHOLAN-24-OIC ACID, 6-ETHYL-3,7-DIHYDROXY-, (3.ALPHA.,5.BETA.,6.ALPHA.,7.ALPHA.)-
  • Cholan-24-oic acid, 6-ethyl-3,7-dihydroxy-, (3alpha,5beta,6alpha,7alpha)-
  • D09360
  • DB05990
  • DSP-1747
  • DSP1747
  • EX-A387
  • GS-6103
  • GTPL3435
  • HY-12222
  • INT 747
  • INT-747
  • INT747
  • MFCD16621104
  • NCGC00480885-01
  • Obetichloic acid
  • Obeticholic acid
  • Obeticholic acid (INT-747)
  • Obeticholic acid (JAN/USAN/INN)
  • Ocaliva
  • P16663
  • Q15708271

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC14164617
  • UNII-0462Z4S4OZ
  • AKOS024259126
  • DTXSID20196671
  • CHEMBL566315
  • CHEBI:43602
  • SCHEMBL715823

Physico-Chemical properties

IUPAC name(4R)-4-[(3R,5S,6R,7R,8S,9S,10S,13R,14S,17R)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
Molecular formulaC26H44O4
Molecular weight420.625
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity122.22
LogP5.1
Topological polar surface area77.8

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.