Basic information
- CAS
401-10-5- Standard SMILES
CC1=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- InChIKey
MTGFYEHKPMOVNE-NEFMKCFNSA-N- Molecular formula
- C26H36O8
- Average molar mass
- 476.6 g/mol
- Monoisotopic mass
- 476.24101811
Overview
1-O-all-trans-retinoyl-beta-glucuronic acid is a retinoid that is retinoic acid in which the carboxy proton has been replaced by a beta-D-glucuronyl residue. It has a role as a human metabolite. It is a retinoid and a member of glucuronic acids. It is functionally related to an all-trans-retinoic acid. It is a conjugate acid of a 1-O-(all-trans-retinoyl)-beta-D-glucuronate.
Names & identifiers
- Preferred name
- Retinoyl beta-glucuronide
- IUPAC
- (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
- English name
- E-Retinoylb-glucuronide
- Molecular formula
- C26H36O8
- Molecular weight
- 476.562
Names & synonyms
Retinoyl beta-glucuronide401-10-5Retinoyl glucuronideXB6RQ16Y55beta-D-Glucopyranuronic acid, 1-retinoate(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 acidDTXSID40274187(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 acidRefChem:930683DTXCID70819949Glucuronideall-trans-Retinoyl-beta-glucuronide
Show more names
Retinoyl-β-D-glucuronide(E-Retinoyl)-β-glucuronideE-Retinoyl β-glucuronide ,85%Retinoyl β-D-glucuronopyranosideRetinoyl-β-D-glucuronopyranoside
Retinoyl b-glucuronide13-cis-Retinoyl glucuronideRetinoyl-beta-glucuronideRetinoic acid beta-D-glucuronideall-trans-Retinoyl-beta-D-glucuronide1-O-all-trans-retinoyl-beta-glucuronic acidE-RETINOYLB-GLUCURONIDETretinoin Glucuronide
Properties
Computed structural properties
- XLogP
- 4.4
- Topological polar surface area
- 134 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 8
- Heavy atoms
- 34
- Formal charge
- 0
- Complexity
- 921
Experimental & physicochemical properties
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> Retinoids [PR0109]
Physical DescriptionSolid
Physicochemical properties
- storage temp.
- -20 °C · Amber Vial, -20°C Freezer, Under Inert Atmosphere
- solubility
- DMSO (Slightly), Water (Slightly)
- form
- Solid
- color
- Light Yellow
- Stability
- Light Sensitive, Temperature Sensitive, Unstable in Solution
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 6 RQ16Y55 · XB6RQ16Y55
- HS Code
- 29389090 · 29389090
Safety & regulation
Safety data
- hs_code
- 29389090
Chemistry & industry
Pharmacology
Metabolism/MetabolitesAll-trans-retinoyl glucuronide is a known human metabolite of Tretinoin.
Tissue LocationsAdipose Tissue
Cellular LocationsCytoplasm
Metabolite PathwaysRetinol Metabolism
Applications
UsesA biliary metabolite of Vitamin A, occurs endogenously in human blood. RAG is biologically active in promoting the growth of vitamin A-deficient rats and the induction of differentiation of HL-60 and BA-HAN-1C cells, but less cytotoxic than Retinoic Acids.
Suppliers12 total
湖北瑞玛标物科技有限公司15787879035 15787875101 · [email protected]
Clearsynth Labs Limited+91-22-26355700 · [email protected]
凯试（上海）科技有限公司021-50135380 · [email protected]
南京熙泽医药科技有限公司025-66023220 15250997978 · [email protected]
上海一研生物科技有限公司021-69985186 13611928337 · [email protected]
BOC Sciences16314854226 · [email protected]
上海宏叶生物科技有限公司400-9205774 400-920-5774 · [email protected]
Related reactions
5 records
Compound notes
Loading…