Retinoyl beta-glucuronide

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

What is the Retinoyl beta-glucuronide?

The molecule Retinoyl beta-glucuronide presents a molecular formula of C26H36O8 and its IUPAC name is (2S,3S,4S,5R,6S)-6-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid.

Retinoyl beta-glucuronide is a molecule that is formed when retinoic acid (a vitamin A derivative) and beta-glucuronidase (an enzyme) combine. This molecule is then transported to the skin, where it can help to reduce the appearance of wrinkles and fine lines. In addition, retinoyl beta-glucuronide has been shown to stimulate the production of collagen, which is the main structural protein in the skin..

3D structure

Cartesian coordinates

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

2D drawing

 

Retinoyl beta-glucuronide MTGFYEHKPMOVNE-NEFMKCFNSA-N chemical compound 2D structure molecule svg
Retinoyl beta-glucuronide

 

Molecule descriptors

 
IUPAC name(2S,3S,4S,5R,6S)-6-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
InChI codeInChI=1S/C26H36O8/c1-15(11-12-18-17(3)10-7-13-26(18,4)5)8-6-9-16(2)14-19(27)33-25-22(30)20(28)21(29)23(34-25)24(31)32/h6,8-9,11-12,14,20-23,25,28-30H,7,10,13H2,1-5H3,(H,31,32)/b9-6+,12-11+,15-8+,16-14+/t20-,21-,22+,23-,25+/m0/s1
InChI KeyMTGFYEHKPMOVNE-NEFMKCFNSA-N
SMILESCC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O)C(C)(C)CCC1

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.

  • (2S,3S,4S,5R,6S)-6-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
  • (2S,3S,4S,5R,6S)-6-{[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
  • .BETA.-D-GLUCOPYRANURONIC ACID, 1-RETINOATE
  • 1-O-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoyl]-beta-D-glucopyranuronic acid
  • 1004517-36-5
  • 13-cis-Retinoyl b-D-glucuronide
  • 13-cis-Retinoyl glucuronide
  • 13-cis-retinoic acid acyl beta-D-glucuronide
  • 13-cis-retinoic acid acyl beta-delta-glucuronide
  • 13-cis-retinoyl-beta-D-glucuronide
  • 13-cis-retinoyl-beta-delta-glucuronide
  • 401-10-5
  • 9-cis-Retinoyl b-D-glucuronide
  • 9-cis-Retinoyl-beta-D-glucuronide
  • 9-cis-Retinoyl-beta-delta-glucuronide
  • ALL-TRANS-RETINOYL .BETA.-D-GLUCURONIDE
  • All-trans-retinoyl B-glucuronide
  • E-RETINOYLB-GLUCURONIDE
  • E-Retinoyl b-glucuronide
  • GLUCOPYRANOSIDURONIC ACID, 1-RETINOATE, .BETA.-D-
  • Glucuronide
  • O(15)-[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl]retinoic acid
  • Q27103934
  • RETINOIC ACID, .BETA.-D-GLUCURONOSYL ESTER
  • RETINOIC ACID, 1-ESTER WITH .BETA.-D-GLUCOPYRANOSIDURONIC ACID
  • RETINOIC ACID, 1-ESTER WITH GLUCOPYRANURONIC ACID
  • RETINOYL .BETA.-GLUCURONIDE
  • RETINOYL GLUCURONIDE, ALL-TRANS
  • Retinoic acid beta-D-glucuronide
  • Retinoic acid beta-delta-glucuronide
  • Retinoyl beta-glucuronide
  • Retinoyl glucuronide
  • Retinoyl-beta-glucuronide
  • Trans-retinoyl glucuronide
  • Tretinoin Glucuronide
  • W-201374
  • W-202656
  • W-203796
  • XB6RQ16Y55
  • all-trans Retinoyl
  • all-trans-Retinoyl-beta-D-glucuronide
  • all-trans-Retinoyl-beta-delta-glucuronide
  • all-trans-Retinoyl-beta-glucuronide
  • all-trans-retinoyl glucuronide
  • beta-D-Glucopyranuronic acid, 1-ester with retinoic acid
  • beta-D-Glucopyranuronic acid, 1-retinoate

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC4098984
  • UNII-XB6RQ16Y55
  • DTXSID40274187
  • CHEBI:28870

Physico-Chemical properties

IUPAC name(2S,3S,4S,5R,6S)-6-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
Molecular formulaC26H36O8
Molecular weight476.559
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity127.87
LogP3.0
Topological polar surface area133.5

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.