ChemFOnt: Showing chemical card for Codeine-6-glucuronide (CFc000040904)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:42:38 UTC

Chemfont ID

CFc000040904

Molecule Identification

Common Name

Codeine-6-glucuronide

Definition

704

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₄H₂₉NO₉

Average Molecular Weight

475.4884

Monoisotopic Molecular Weight

475.184231531

IUPAC Name

(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7,9,11(18),15-tetraen-14-yl]oxy}oxane-2-carboxylic acid

Traditional Name

codeine-6-glucuronide

CAS Registry Number

20736-11-2

SMILES

[H][C@]12C=C[C@H](O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@@H]3OC4=C5C(C[C@H]1N(C)CC[C@@]235)=CC=C4OC

InChI Identifier

InChI=1S/C24H29NO9/c1-25-8-7-24-11-4-6-14(32-23-18(28)16(26)17(27)20(34-23)22(29)30)21(24)33-19-13(31-2)5-3-10(15(19)24)9-12(11)25/h3-6,11-12,14,16-18,20-21,23,26-28H,7-9H2,1-2H3,(H,29,30)/t11-,12+,14-,16-,17-,18+,20-,21-,23+,24-/m0/s1

InChI Key

CRWVOYRJXPDBPM-HSCJLHHPSA-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
O-glucuronide
1-o-glucuronide
Phenanthrene
Glucuronic acid or derivatives
O-glycosyl compound
Glycosyl compound
Tetralin
Coumaran
Anisole
Alkyl aryl ether
Beta-hydroxy acid
Aralkylamine
Hydroxy acid
Oxane
Monosaccharide
Piperidine
Benzenoid
Pyran
Amino acid or derivatives
Amino acid
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Acetal
Carboxylic acid derivative
Carboxylic acid
Ether
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Polyol
Organic nitrogen compound
Alcohol
Amine
Hydrocarbon derivative
Organic oxygen compound
Organopnictogen compound
Organic oxide
Carbonyl group
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

morphinane alkaloid (CHEBI:80580 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 9448068)

Organ

Liver (HMDB: HMDB0060464)
Kidney (HMDB: HMDB0060464)

Excreta

Biofluid or Excreta

Urine (PMID: 16258895)

Cellular substructure

Microsomes (HMDB: HMDB0060464)

Source

Endogenous

Endogenous (HMDB: HMDB0060464)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Codeine Action Pathway (PathBank: SMP0000405)

Metabolic pathway

Codeine Metabolism Pathway (PathBank: SMP0000621)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	4.31 g/L	ALOGPS
logP	-0.23	ALOGPS
logP	-2.8	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	2.87	ChemAxon
pKa (Strongest Basic)	9.19	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	138.15 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	116.89 m³·mol⁻¹	ChemAxon
Polarizability	47.27 Å³	ChemAxon
Number of Rings	6	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

HMDB0060464

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

C16577

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Codeine-6-glucuronide

METLIN ID

Not Available

PubChem Compound

5489029

PDB ID

Not Available

ChEBI ID

80580

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Srinivasan, Vinayak; Wielbo, Donna; Simpkins, James; Karlix, Janet; Sloan, Kenneth; Tebbett, Ian, 1996: Analgesic and immunomodulatory effects of codeine and codeine 6-glucuronide. Pharmaceutical Research (new York). 13(2): 296-300

Showing chemical card for Codeine-6-glucuronide (CFc000040904)

MOL for CFc000040904 (Codeine-6-glucuronide)

3D MOL for CFc000040904 (Codeine-6-glucuronide)

3D SDF for CFc000040904 (Codeine-6-glucuronide)

3D-SDF for CFc000040904 (Codeine-6-glucuronide)

PDB for CFc000040904 (Codeine-6-glucuronide)

3D PDB for CFc000040904 (Codeine-6-glucuronide)

SMILES for CFc000040904 (Codeine-6-glucuronide)

INCHI for CFc000040904 (Codeine-6-glucuronide)

Structure for CFc000040904 (Codeine-6-glucuronide)

3D Structure for CFc000040904 (Codeine-6-glucuronide)