ChemFOnt: Showing chemical card for Dextrorphan O-glucuronide (CFc000006349)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:52:19 UTC

Chemfont ID

CFc000006349

Molecule Identification

Common Name

Dextrorphan O-glucuronide

Definition

Dextrorphan O-glucuronide is a natural human metabolite of Dextrorphan generated in the liver by UDP glucuonyltransferase. Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Dextrorphan O-glucuronide	ChEBI
Dextrorphan O-glucosiduronate	Generator

Chemical Formula

C₂₃H₃₁NO₇

Average Molecular Weight

433.4947

Monoisotopic Molecular Weight

433.210052351

IUPAC Name

(2S,3S,4S,5R)-3,4,5-trihydroxy-6-{[(1S,9S,10S)-17-methyl-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,5-trien-4-yl]oxy}oxane-2-carboxylic acid

Traditional Name

dextrorphan O-glucuronide

CAS Registry Number

None

SMILES

[H][C@]12CCCC[C@]11CCN(C)[C@H]2CC2=C1C=C(OC1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C=C2

InChI Identifier

InChI=1S/C23H31NO7/c1-24-9-8-23-7-3-2-4-14(23)16(24)10-12-5-6-13(11-15(12)23)30-22-19(27)17(25)18(26)20(31-22)21(28)29/h5-6,11,14,16-20,22,25-27H,2-4,7-10H2,1H3,(H,28,29)/t14-,16+,17+,18+,19-,20+,22?,23+/m1/s1

InChI Key

YQAUTKINOXBFCA-DCWOAAMISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Morphinans

Sub Class

Not Available

Direct Parent

Morphinans

Alternative Parents

Substituents

Morphinan
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Phenolic glycoside
1-o-glucuronide
O-glucuronide
Phenanthrene
Glucuronic acid or derivatives
Alkyl glycoside
Benzazocine
Glycosyl compound
O-glycosyl compound
Tetralin
Beta-hydroxy acid
Aralkylamine
Hydroxy acid
Monosaccharide
Fatty acyl
Pyran
Oxane
Piperidine
Benzenoid
Amino acid
Tertiary amine
Secondary alcohol
Amino acid or derivatives
Tertiary aliphatic amine
Oxacycle
Acetal
Carboxylic acid derivative
Azacycle
Carboxylic acid
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Polyol
Alcohol
Organic oxygen compound
Organopnictogen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organonitrogen compound
Amine
Organic nitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

glucosiduronic acid (CHEBI:32645 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0010341)

Organ

Liver (HMDB: HMDB0010341)
Kidney (HMDB: HMDB0010341)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0010341)

Cellular substructure

Cytoplasm (HMDB: HMDB0010341)

Source

Endogenous

Endogenous (HMDB: HMDB0010341)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Biological role

Drug metabolite (HMDB: HMDB0010341)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.2 g/L	ALOGPS
logP	1.38	ALOGPS
logP	-1.3	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	2.85	ChemAxon
pKa (Strongest Basic)	9.82	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	119.69 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	110.09 m³·mol⁻¹	ChemAxon
Polarizability	44.93 Å³	ChemAxon
Number of Rings	5	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24883428

PDB ID

Not Available

ChEBI ID

32645

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Dextrorphan O-glucuronide (CFc000006349)

MOL for CFc000006349 (Dextrorphan O-glucuronide)

3D MOL for CFc000006349 (Dextrorphan O-glucuronide)

3D SDF for CFc000006349 (Dextrorphan O-glucuronide)

3D-SDF for CFc000006349 (Dextrorphan O-glucuronide)

PDB for CFc000006349 (Dextrorphan O-glucuronide)

3D PDB for CFc000006349 (Dextrorphan O-glucuronide)

SMILES for CFc000006349 (Dextrorphan O-glucuronide)

INCHI for CFc000006349 (Dextrorphan O-glucuronide)

Structure for CFc000006349 (Dextrorphan O-glucuronide)

3D Structure for CFc000006349 (Dextrorphan O-glucuronide)