Metabolism Reactions

Aromatic Hydroxylation

Very Likely

Prefers Para Position

EWG Make Rxn "Possible"

Alkene Epoxidation

Likely

*Show Intermediate*

Needs Unconjugated Double bond

Alkene Reduction

"Possible"

Requires an Unconjugated Double Bond

Double Bond -> Single Bond

Benzylic Oxidation

Likely

Steric hindrance can make it "Possible"

Affected by EWG/EDG

Requires Benzene Ring

Adds -OH

Allylic Hydroxylation

Likely

Affects Carbon Adjacent to Double Bond (Allylic)

Requires Alpha Hydrogen

Affected by Sterics

Oxidation at Carbon Atoms α to both a Carbonyl & Imine

Likely

Requires both an Imine (=N) and Carbonyl (=O) with a single carbon between them

Adds -OH

Omega (ω) Oxidation

"Possible"

Occurs at terminal (ω) or next to terminal (ω-1) C atom

Adds -OH; Can be further metabolized to Carboxylic acid

X-Dealkylation

Likely

X=N/O/S

Requires a free Alpha proton

Targets smaller Alkyl group as the leaving group

Deaminiation

Likely

Needs free Alpha Carbon of Primary (1°) Amine

Amine is leaving group

Lactam (N) / Lactone (O) formation

Likely

Requires free Alpha Carbon

Adds a Carbonyl adjacent to N/O

S-Oxidation

Likely

N-Oxidation

"Possible"

Requires Aromatic Ring

Thiols to Disulfide

Likely

Two SH Groups bond to make a larger structure bound by S-S

Disulfide to Thiols

"Possible"

S-S Bond break to form 2 smaller structures

Aldehyde Oxidation

Likely

Forms Carboxylic Acid

Dehydrohalogenation

Likely

Pick best leaving group/atom first

I > Br > Cl

Ketone Reduction

Likely

Aromatic Azo Reduction

Possible

Similar to Disulfide to 2 Thiols

Aromatic Nitro Reduction

Possible

Nitrile Oxidation

Possible

Needs an alpha proton

C≡N comes off as CN(-)

Amide Hydrolysis

Likely

Requires 2° Amide

"Possible" With an Ester

Ester Hydrolysis

Likely

Cleaves O of Ester and replaces it with -OH

Desulfuration

"Possible"

Replaces =S with =O

Glucuronic Acid Conjugation

Likely

Alcohols, Phenols, Alkyl Acids, 1°/2° Amines, Alkyl Acids

"Possible"

Thiols

UDPGA

UDP-Glucuronyl transferase

Sulfate Conjugation

Likely

Phenols, Alcohols

"Possible"

Nitrogens

PAPS

Sulfotransferase

Glycine/Glutamine Conjugation

Likely

Aromatic Acids

"Possible"

Alkyl Acids

ATP, CoASH

Glycine/Glutamine N-Acetyl transferase

GSH Conjugation

"Possible" (due to limited amount of GSH)

Br, Cl, I, OSO3, OPO(OR)2, Must be at a reactive center

GSH

Glutathione S-Transferase

Acetylation

Likely

Aromatic Amines

"Possible"

Alkyl Amines

AcetylCoA

N-Acetyl Transferase

Methylation

"Possible"

Alcohols, Phenols, Amines, Thiols

SAM

COMT