Reaction participants Show >> << Hide
- Name help_outline O2 Identifier CHEBI:15379 (CAS: 7782-44-7) help_outline Charge 0 Formula O2 InChIKeyhelp_outline MYMOFIZGZYHOMD-UHFFFAOYSA-N SMILEShelp_outline O=O 2D coordinates Mol file for the small molecule Search links Involved in 2,648 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
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Namehelp_outline
reduced [NADPH—hemoprotein reductase]
Identifier
RHEA-COMP:11964
Reactive part
help_outline
- Name help_outline FMNH2 Identifier CHEBI:57618 (Beilstein: 6258176) help_outline Charge -2 Formula C17H21N4O9P InChIKeyhelp_outline YTNIXZGTHTVJBW-SCRDCRAPSA-L SMILEShelp_outline Cc1cc2Nc3c([nH]c(=O)[nH]c3=O)N(C[C@H](O)[C@H](O)[C@H](O)COP([O-])([O-])=O)c2cc1C 2D coordinates Mol file for the small molecule Search links Involved in 771 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline testosterone Identifier CHEBI:17347 (Beilstein: 3653705,1915399; CAS: 58-22-0) help_outline Charge 0 Formula C19H28O2 InChIKeyhelp_outline MUMGGOZAMZWBJJ-DYKIIFRCSA-N SMILEShelp_outline [H][C@@]12CCC3=CC(=O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@@H](O)CC[C@@]21[H] 2D coordinates Mol file for the small molecule Search links Involved in 18 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 16α,17β-dihydroxyandrost-4-en-3-one Identifier CHEBI:34172 (CAS: 63-01-4) help_outline Charge 0 Formula C19H28O3 InChIKeyhelp_outline YMCWOAZGWMZGQT-FPNLOETNSA-N SMILEShelp_outline C1C(C=C2[C@](C1)([C@@]3([C@@](CC2)([C@@]4([H])[C@@](CC3)(C)[C@H]([C@@H](C4)O)O)[H])[H])C)=O 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H+ Identifier CHEBI:15378 Charge 1 Formula H InChIKeyhelp_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILEShelp_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,176 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H2O Identifier CHEBI:15377 (Beilstein: 3587155; CAS: 7732-18-5) help_outline Charge 0 Formula H2O InChIKeyhelp_outline XLYOFNOQVPJJNP-UHFFFAOYSA-N SMILEShelp_outline [H]O[H] 2D coordinates Mol file for the small molecule Search links Involved in 6,048 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
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Namehelp_outline
oxidized [NADPH—hemoprotein reductase]
Identifier
RHEA-COMP:11965
Reactive part
help_outline
- Name help_outline FMN Identifier CHEBI:58210 Charge -3 Formula C17H18N4O9P InChIKeyhelp_outline ANKZYBDXHMZBDK-SCRDCRAPSA-K SMILEShelp_outline C12=NC([N-]C(C1=NC=3C(N2C[C@@H]([C@@H]([C@@H](COP(=O)([O-])[O-])O)O)O)=CC(=C(C3)C)C)=O)=O 2D coordinates Mol file for the small molecule Search links Involved in 781 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:53196 | RHEA:53197 | RHEA:53198 | RHEA:53199 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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Anandamide oxidation by wild-type and polymorphically expressed CYP2B6 and CYP2D6.
Sridar C., Snider N.T., Hollenberg P.F.
Anandamide is an arachidonic acid-derived endogenous cannabinoid that regulates normal physiological functions and pathophysiological responses within the central nervous system and in the periphery. Several cytochrome P450 (P450) isoforms metabolize anandamide to form hydroxylated and epoxygenate ... >> More
Anandamide is an arachidonic acid-derived endogenous cannabinoid that regulates normal physiological functions and pathophysiological responses within the central nervous system and in the periphery. Several cytochrome P450 (P450) isoforms metabolize anandamide to form hydroxylated and epoxygenated products. Human CYP2B6 and CYP2D6, which are expressed heterogeneously throughout the brain, exhibit clinically significant polymorphisms and are regulated by external factors, such as alcohol and smoking. Oxidative metabolism of anandamide by these two P450s may have important functional consequences for endocannabinoid system signaling. In this study, we investigated the metabolism of anandamide by wild-type CYP2B6 (2B6.1) and CYP2D6 (2D6.1) and by their common polymorphic mutants 2B6.4, 2B6.6, 2B6.9, and 2D6.34. Major differences in anandamide metabolism by the two isoforms and their mutants were found in vitro with respect to the formation of 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 14,15-epoxyeicosatetraenoic acid ethanolamide (14,15-EET-EA). Pharmacological studies showed that both 20-HETE-EA and 14,15-EET-EA bind to the rat brain cannabinoid CB1 receptor with lower affinities relative to that of anandamide. In addition, both products are degraded more rapidly than anandamide in rat brain homogenates. Their degradation occurs via different mechanisms involving either fatty acid amide hydrolase (FAAH), the major anandamide-degrading enzyme, or epoxide hydrolase (EH). Thus, the current findings provide potential new insights into the actions of inhibitors FAAH and EH, which are being developed as novel therapeutic agents, as well as a better understanding of the interactions between the cytochrome P450 monooxygenases and the endocannabinoid system. << Less
Drug Metab. Dispos. 39:782-788(2011) [PubMed] [EuropePMC]
This publication is cited by 5 other entries.
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Purification and characterization of three male-specific and one female-specific forms of cytochrome P-450 from rat liver microsomes.
Matsumoto T., Emi Y., Kawabata S., Omura T.
Three forms of cytochrome P-450, tentatively designated P-450(M-1), P-450(M-2), and P-450(M-3), and one form of cytochrome P-450, P-450(F-1), were purified from the liver microsomes of untreated male and female rats, respectively. Each purified form of the cytochrome showed a single protein band o ... >> More
Three forms of cytochrome P-450, tentatively designated P-450(M-1), P-450(M-2), and P-450(M-3), and one form of cytochrome P-450, P-450(F-1), were purified from the liver microsomes of untreated male and female rats, respectively. Each purified form of the cytochrome showed a single protein band on SDS-polyacrylamide gel electrophoresis, and gave a minimum molecular weight of 51,000 for P-450(M-1), 48,000 for P-450(M-2), 49,000 for P-450(M-3), and 50,000 for P-450(F-1). The carbon monoxide-difference spectra of reduced P-450(M-1), P-450(M-2), P-450(M-3), and P-450(F-1) showed an absorption maximum at 451, 451, 448, and 449 nm, respectively. Judging from the absolute absorption spectra, the four forms of cytochrome P-450 were of low-spin type in the oxidized forms. The antibodies against P-450(M-2) did not crossreact with the other forms in the Ouchterlony double diffusion test, whereas the immunodiffusion test showed immunocrossreactivity between P-450(M-1) and P-450(F-1), P-450(M-1) and P-450(M-3), and P-450(M-3) and P-450(F-1). The NH2-terminal amino acid sequences of the four forms confirmed that they were different molecular species, although significant homology was noticed among P-450(M-1), P-450(M-3), and P-450(F-1). The quantitation of P-450(M-1) and P-450(F-1) in liver microsomes by quantitative immunoprecipitation confirmed that these two forms of cytochrome P-450 were developmentally induced in male and female rats, respectively. P-450(M-2) was also developmentally induced in male rats. In a reconstituted system containing NADPH and NADPH-cytochrome P-450 reductase, P-450(M-1) oxidized benzphetamine at a high rate, whereas the other forms had low activity toward benzphetamine. None of the four forms showed high activity toward benzo(a)pyrene. P-450(M-1) catalyzed the hydroxylation testosterone at the 16 alpha and 2 alpha positions, whereas P-450(M-2) catalyzed the 15 alpha hydroxylation of the same substrate. << Less
J. Biochem. 100:1359-1371(1986) [PubMed] [EuropePMC]
This publication is cited by 1 other entry.