NP-MRD: Showing NP-Card for Retinoyl beta-glucuronide (NP0087028)

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Record Information

Version

2.0

Created at

2022-05-11 16:37:50 UTC

Updated at

2022-05-11 16:37:50 UTC

NP-MRD ID

NP0087028

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Retinoyl beta-glucuronide

Description

Retinoyl b-glucuronide, also known as 13-cis-retinoate, belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. Retinoyl b-glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa). Retinoyl b-glucuronide can be biosynthesized from all-trans-retinoic acid through the action of the enzyme UDP-glucuronosyltransferase 1-1. In humans, retinoyl b-glucuronide is involved in retinol metabolism. Retinoyl beta-glucuronide was first documented in 1995 (PMID: 8565776). A retinoid that is Retinoyl b-glucuronide in which the carboxy proton has been replaced by a beta-D-glucuronyl residue (PMID: 16183782) (PMID: 16988123) (PMID: 15334623) (PMID: 8867997) (PMID: 9929509) (PMID: 15470160).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231219392D          

 34 35  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv0541 02231219392D          

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M  END
> <DATABASE_ID>
NP0087028

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@@H](O)[C@@H](O[C@H](C(O)=O)[C@H]1O)OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C

> <INCHI_IDENTIFIER>
InChI=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_KEY>
MTGFYEHKPMOVNE-NEFMKCFNSA-N

> <FORMULA>
C26H36O8

> <MOLECULAR_WEIGHT>
476.5592

> <EXACT_MASS>
476.241018128

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
51.85115996977926

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(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

> <ALOGPS_LOGP>
3.57

> <JCHEM_LOGP>
3.2999074889999997

> <ALOGPS_LOGS>
-4.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.212250468844253

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.389209916695899

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6869063371000665

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
130.0894

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glucuronide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      42.334 -32.015   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      42.334 -35.095   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      45.002 -36.635   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      47.669 -35.095   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      47.669 -30.474   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      45.002 -32.015   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      49.003 -32.785   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      43.668 -29.704   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      36.436 -17.591   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      37.206 -18.924   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      42.334 -27.394   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      39.667 -22.774   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      34.332 -22.774   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      35.666 -18.924   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      43.668 -32.785   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      43.668 -34.325   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      45.002 -35.095   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      46.335 -34.325   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      46.335 -32.785   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      34.332 -18.154   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      32.998 -18.924   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      32.998 -20.464   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      47.669 -32.015   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      42.334 -30.474   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      41.001 -28.164   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      38.333 -23.544   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      41.001 -29.704   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      38.333 -25.084   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      39.667 -27.394   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      39.667 -25.854   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      36.999 -22.774   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      36.999 -21.234   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      34.332 -21.234   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      35.666 -20.464   0.000  0.00  0.00           C+0
CONECT    1   15   24                                                       
CONECT    2   16                                                            
CONECT    3   17                                                            
CONECT    4   18                                                            
CONECT    5   23                                                            
CONECT    6   15   19                                                       
CONECT    7   23                                                            
CONECT    8   24                                                            
CONECT    9   14                                                            
CONECT   10   14                                                            
CONECT   11   25                                                            
CONECT   12   26                                                            
CONECT   13   33                                                            
CONECT   14    9   10   20   34                                             
CONECT   15    1    6   16                                                  
CONECT   16    2   15   17                                                  
CONECT   17    3   16   18                                                  
CONECT   18    4   17   19                                                  
CONECT   19    6   18   23                                                  
CONECT   20   14   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   33                                                       
CONECT   23    5    7   19                                                  
CONECT   24    1    8   27                                                  
CONECT   25   11   27   29                                                  
CONECT   26   12   28   31                                                  
CONECT   27   24   25                                                       
CONECT   28   26   30                                                       
CONECT   29   25   30                                                       
CONECT   30   28   29                                                       
CONECT   31   26   32                                                       
CONECT   32   31   34                                                       
CONECT   33   13   22   34                                                  
CONECT   34   14   32   33                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

View in JSmol

Synonyms

Value	Source
all-trans-Retinoyl-beta-glucuronide	ChEBI
Retinoyl glucuronide	ChEBI
all-trans-Retinoyl-b-glucuronide	Generator
all-trans-Retinoyl-β-glucuronide	Generator
13-cis-Retinoate	HMDB
13-cis-Retinoic acid	HMDB
13-cis-Retinoic acid acyl beta-D-glucuronide	HMDB
13-cis-Retinoic acid acyl beta-delta-glucuronide	HMDB
13-cis-Retinoyl glucuronide	HMDB
13-cis-Retinoyl-beta-D-glucuronide	HMDB
13-cis-Retinoyl-beta-delta-glucuronide	HMDB
13-cis-Retinoyl-beta-glucuronide	HMDB
9-cis-Retinoyl-beta-D-glucuronide	HMDB
9-cis-Retinoyl-beta-delta-glucuronide	HMDB
all-trans-Retinoyl-beta-D-glucuronide	HMDB
all-trans-Retinoyl-beta-delta-glucuronide	HMDB
Glucuronide	HMDB
Retinoate	HMDB
Retinoic acid	HMDB
Retinoic acid beta-D-glucuronide	HMDB
Retinoic acid beta-delta-glucuronide	HMDB
Retinoyl beta-glucuronide	HMDB
Retinoyl-beta-glucuronide	HMDB
trans-Retinoyl glucuronide	HMDB

Chemical Formula

C₂₆H₃₆O₈

Average Mass

476.5592 Da

Monoisotopic Mass

476.24102 Da

IUPAC Name

(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

Traditional Name

glucuronide

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](O)[C@@H](O[C@H](C(O)=O)[C@H]1O)OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C

InChI Identifier

InChI=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 Key

MTGFYEHKPMOVNE-NEFMKCFNSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Retinoid ester
Diterpenoid
Retinoid skeleton
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
Beta-hydroxy acid
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Hydroxy acid
Monosaccharide
Oxane
Pyran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organoheterocyclic compound
Polyol
Oxacycle
Acetal
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

glucuronic acids (CHEBI:28870 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.57	ALOGPS
logP	3.3	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	3.39	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	130.09 m³·mol⁻¹	ChemAxon
Polarizability	51.85 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0003141

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023112

KNApSAcK ID

Not Available

Chemspider ID

4445170

KEGG Compound ID

C11061

BioCyc ID

Not Available

BiGG ID

2304843

Wikipedia Link

Not Available

METLIN ID

2280

PubChem Compound

5281877

PDB ID

Not Available

ChEBI ID

28870

Good Scents ID

Not Available

References

General References

Kochansky CJ, Xia YQ, Wang S, Cato B, Creighton M, Vincent SH, Franklin RB, Reed JR: Species differences in the elimination of a peroxisome proliferator-activated receptor agonist highlighted by oxidative metabolism of its acyl glucuronide. Drug Metab Dispos. 2005 Dec;33(12):1894-904. Epub 2005 Sep 23. [PubMed:16183782 ]
Niles RM, Cook CP, Meadows GG, Fu YM, McLaughlin JL, Rankin GO: Resveratrol is rapidly metabolized in athymic (nu/nu) mice and does not inhibit human melanoma xenograft tumor growth. J Nutr. 2006 Oct;136(10):2542-6. doi: 10.1093/jn/136.10.2542. [PubMed:16988123 ]
Ghosal A, Yuan Y, Hapangama N, Su AD, Alvarez N, Chowdhury SK, Alton KB, Patrick JE, Zbaida S: Identification of human UDP-glucuronosyltransferase enzyme(s) responsible for the glucuronidation of 3-hydroxydesloratadine. Biopharm Drug Dispos. 2004 Sep;25(6):243-52. doi: 10.1002/bdd.405. [PubMed:15334623 ]
Brunelle FM, Verbeeck RK: Glucuronidation of diflunisal in liver and kidney microsomes of rat and man. Xenobiotica. 1996 Feb;26(2):123-31. doi: 10.3109/00498259609046694. [PubMed:8867997 ]
Sass JO, Masgrau E, Saurat JH, Nau H: Metabolism of oral 9-cis-retinoic acid in the human. Identification of 9-cis-retinoyl-beta-glucuronide and 9-cis-4-oxo-retinoyl-beta-glucuronide as urinary metabolites. Drug Metab Dispos. 1995 Sep;23(9):887-91. [PubMed:8565776 ]
Calabrese CR, Loadman PM, Lim LS, Bibby MC, Double JA, Brown JE, Lamb JH: In vivo metabolism of the antitumor imidazoacridinone C1311 in the mouse and in vitro comparison with humans. Drug Metab Dispos. 1999 Feb;27(2):240-5. [PubMed:9929509 ]
Yamanaka H, Nakajima M, Katoh M, Kanoh A, Tamura O, Ishibashi H, Yokoi T: Trans-3'-hydroxycotinine O- and N-glucuronidations in human liver microsomes. Drug Metab Dispos. 2005 Jan;33(1):23-30. doi: 10.1124/dmd.104.001701. Epub 2004 Oct 6. [PubMed:15470160 ]
Sperker B, Murdter TE, Schick M, Eckhardt K, Bosslet K, Kroemer HK: Interindividual variability in expression and activity of human beta-glucuronidase in liver and kidney: consequences for drug metabolism. J Pharmacol Exp Ther. 1997 May;281(2):914-20. [PubMed:9152401 ]
Kosoglou T, Statkevich P, Johnson-Levonas AO, Paolini JF, Bergman AJ, Alton KB: Ezetimibe: a review of its metabolism, pharmacokinetics and drug interactions. Clin Pharmacokinet. 2005;44(5):467-94. doi: 10.2165/00003088-200544050-00002. [PubMed:15871634 ]
Moss T, Howes D, Williams FM: Percutaneous penetration and dermal metabolism of triclosan (2,4, 4'-trichloro-2'-hydroxydiphenyl ether). Food Chem Toxicol. 2000 Apr;38(4):361-70. doi: 10.1016/s0278-6915(99)00164-7. [PubMed:10722890 ]
Cunha PD, Lord RS, Johnson ST, Wilker PR, Aster RH, Bougie DW: Immune hemolytic anemia caused by sensitivity to a metabolite of etodolac, a nonsteroidal anti-inflammatory drug. Transfusion. 2000 Jun;40(6):663-8. doi: 10.1046/j.1537-2995.2000.40060663.x. [PubMed:10864985 ]
Nordin C, Bertilsson L: Active hydroxymetabolites of antidepressants. Emphasis on E-10-hydroxy-nortriptyline. Clin Pharmacokinet. 1995 Jan;28(1):26-40. doi: 10.2165/00003088-199528010-00004. [PubMed:7712660 ]
Johnson AG, Rigby RJ, Taylor PJ, Jones CE, Allen J, Franzen K, Falk MC, Nicol D: The kinetics of mycophenolic acid and its glucuronide metabolite in adult kidney transplant recipients. Clin Pharmacol Ther. 1999 Nov;66(5):492-500. doi: 10.1016/S0009-9236(99)70012-3. [PubMed:10579476 ]
Oswald S, Haenisch S, Fricke C, Sudhop T, Remmler C, Giessmann T, Jedlitschky G, Adam U, Dazert E, Warzok R, Wacke W, Cascorbi I, Kroemer HK, Weitschies W, von Bergmann K, Siegmund W: Intestinal expression of P-glycoprotein (ABCB1), multidrug resistance associated protein 2 (ABCC2), and uridine diphosphate-glucuronosyltransferase 1A1 predicts the disposition and modulates the effects of the cholesterol absorption inhibitor ezetimibe in humans. Clin Pharmacol Ther. 2006 Mar;79(3):206-17. doi: 10.1016/j.clpt.2005.11.004. Epub 2006 Feb 7. [PubMed:16513445 ]
Kenny JR, Maggs JL, Tettey JN, Harrell AW, Parker SG, Clarke SE, Park BK: Formation and protein binding of the acyl glucuronide of a leukotriene B4 antagonist (SB-209247): relation to species differences in hepatotoxicity. Drug Metab Dispos. 2005 Feb;33(2):271-81. doi: 10.1124/dmd.104.001677. Epub 2004 Nov 2. [PubMed:15523047 ]

Showing NP-Card for Retinoyl beta-glucuronide (NP0087028)

MOL for NP0087028 (Retinoyl beta-glucuronide)

3D MOL for NP0087028 (Retinoyl beta-glucuronide)

3D SDF for NP0087028 (Retinoyl beta-glucuronide)

3D-SDF for NP0087028 (Retinoyl beta-glucuronide)

PDB for NP0087028 (Retinoyl beta-glucuronide)

3D PDB for NP0087028 (Retinoyl beta-glucuronide)

SMILES for NP0087028 (Retinoyl beta-glucuronide)

INCHI for NP0087028 (Retinoyl beta-glucuronide)

Structure for NP0087028 (Retinoyl beta-glucuronide)

3D Structure for NP0087028 (Retinoyl beta-glucuronide)