Salutaridine

Salutaridine
Names
	IUPAC name 4-Hydroxy-3,6-dimethoxy-17-methyl-5,6,8,14-tetradehydromorphinan-7-one
	Systematic IUPAC name (4aS,10R)-5-Hydroxy-3,6-dimethoxy-11-methyl-9,10-dihydro-2H-10,4a-(azanoethano)phenanthren-2-one
Identifiers
CAS Number	1936-18-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17225 ;
ChEMBL	ChEMBL404097 ;
ChemSpider	16736005 ;
KEGG	C05179 ;
PubChem CID	5408233;
UNII	7X10PRH74D ;
CompTox Dashboard (EPA)	DTXSID60941041 ;
	InChI InChI=1S/C19H21NO4/c1-20-7-6-19-10-16(24-3)14(21)9-12(19)13(20)8-11-4-5-15(23-2)18(22)17(11)19/h4-5,9-10,13,22H,6-8H2,1-3H3/t13-,19+/m1/s1 Key: GVTRUVGBZQJVTF-YJYMSZOUSA-N ;
	SMILES CN1CC[C@]23C=C(C(=O)C=C2[C@H]1CC4=C3C(=C(C=C4)OC)O)OC;
Properties
Chemical formula	C19H21NO4
Molar mass	327.380 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Salutaridine, also known as floripavine, is an alkaloid that is present in the morphinan alkaloid pathway of opium poppy, Papaver somniferum.

Biosynthesis

It is produced by the enzyme salutaridine synthase that catalyzes the chemical reaction from its precursor (R)-reticuline:^[1]^[2]

2D representation of the chemical structure of Q82096614.

(R)-reticuline

+ NADPH

O₂

2 H₂O

Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right

salutaridine

+ NADP⁺

The enzyme uses reduced nicotinamide adenine dinucleotide phosphate (NADPH) as its cofactor.

Salutaridine is converted to salutaridinol by the enzyme salutaridine reductase (NADPH).^[3]

salutaridine

+ NADPH

H⁺

Rightward reaction arrow with minor product(s) to top right

salutaridinol

+ NADP⁺

References

^ Enzyme 1.14.19.67 at KEGG Pathway Database.
^ Gerady R, Zenk MH (1993). "Formation of salutaridine from (R)-reticuline by a membrane-bound cytochrome P-450 enzyme from Papaver somniferum". Phytochemistry. 32: 79–86. doi:10.1016/0031-9422(92)80111-Q.
^ Gerady R, Zenk MH (1993). "Purification and characterization of salutaridine:NADPH 7-oxidoreductase from Papaver somniferum". Phytochemistry. 34 (1): 125–132. Bibcode:1993PChem..34..125G. doi:10.1016/S0031-9422(00)90793-3.

[1] Enzyme 1.14.19.67 at KEGG Pathway Database.

[2] Gerady R, Zenk MH (1993). "Formation of salutaridine from (R)-reticuline by a membrane-bound cytochrome P-450 enzyme from Papaver somniferum". Phytochemistry. 32: 79–86. doi:10.1016/0031-9422(92)80111-Q.

[3] Gerady R, Zenk MH (1993). "Purification and characterization of salutaridine:NADPH 7-oxidoreductase from Papaver somniferum". Phytochemistry. 34 (1): 125–132. Bibcode:1993PChem..34..125G. doi:10.1016/S0031-9422(00)90793-3.

[1]

[2]

[3]