Rhea - reaction knowledgebase

Enzymes

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Reaction participants Show >> << Hide

Name ^help_outline a secondary alcohol Identifier CHEBI:35681 Charge 0 Formula CH2OR2 SMILES^help_outline *C(*)O 2D coordinates Mol file for the small molecule Search links Involved in 675 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline NADP⁺ Identifier CHEBI:58349 Charge -3 Formula C21H25N7O17P3 InChIKey^help_outline XJLXINKUBYWONI-NNYOXOHSSA-K SMILES^help_outline NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OC[C@H]2O[C@H]([C@H](OP([O-])([O-])=O)[C@@H]2O)n2cnc3c(N)ncnc23)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 1,316 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline a ketone Identifier CHEBI:17087 Charge 0 Formula COR2 SMILES^help_outline [*]C([*])=O 2D coordinates Mol file for the small molecule Search links Involved in 1,167 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline NADPH Identifier CHEBI:57783 (Beilstein: 10411862) ^help_outline Charge -4 Formula C21H26N7O17P3 InChIKey^help_outline ACFIXJIJDZMPPO-NNYOXOHSSA-J SMILES^help_outline NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OC[C@H]2O[C@H]([C@H](OP([O-])([O-])=O)[C@@H]2O)n2cnc3c(N)ncnc23)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 1,310 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 InChIKey^help_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILES^help_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,717 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule

Cross-references

	RHEA:19257	RHEA:19258	RHEA:19259	RHEA:19260
Reaction direction	undefined	left-to-right	right-to-left	bidirectional
UniProtKB ^help_outline	2,789 proteins	1 proteins	2,169 proteins
EC numbers ^help_outline	1.1.1.2 1.1.1.184
Gene Ontology ^help_outline	GO:0004090
KEGG ^help_outline				R03557
MetaCyc ^help_outline	CARBONYL-REDUCTASE-NADPH-RXN

Related reactions ^help_outline

Specific form(s) of this reaction

RHEA:82232
(S)-3-chloro-1-phenyl-1-propanol + NADP⁺ => 3-chloro-1-phenyl-1-propanone + NADPH + H⁺
RHEA:81720
2,5-hexanedione + 2 NADPH + 2 H⁺ => (2S,5S)-hexanediol + 2 NADP⁺
RHEA:81585
2-amino-3-hydroxy-octadecane-1-sulfonate + NADP⁺ => 2-amino-3-oxo-octadecane-1-sulfonate + NADPH + H⁺
RHEA:81577
capnine + NADP⁺ => 3-oxocapnine + NADPH + H⁺
RHEA:74708
fumagillol + NADP⁺ => 5-dehydrofumagillol + NADPH + H⁺
RHEA:70220
corticosterone + NADPH + H⁺ => 20β-dihydrocorticosterone + NADP⁺
RHEA:70216
cortisol + NADPH + H⁺ => 20β-dihydrocortisol + NADP⁺
RHEA:69285
a 17β-hydroxy steroid + NADP⁺ => a 17-oxo steroid + NADPH + H⁺
RHEA:68150
(2R)-octan-2-ol + NADP⁺ => 2-octanone + NADPH + H⁺
RHEA:68146
ethyl (R)-3-hydroxybutanoate + NADP⁺ => ethyl 3-oxobutanoate + NADPH + H⁺
RHEA:68142
(2R,5R)-hexanediol + 2 NADP⁺ => 2,5-hexanedione + 2 NADPH + 2 H⁺
RHEA:68138
(R)-1-phenylethanol + NADP⁺ => acetophenone + NADPH + H⁺
RHEA:65498
3β,20α-dihydroxy-5β-pregnane + NADP⁺ => 3β-hydroxy-5β-pregnane-20-one + NADPH + H⁺
RHEA:65061
taurochenodeoxycholate + NADP⁺ => 7-oxotaurolithocholate + NADPH + H⁺
RHEA:65057
glycochenodeoxycholate + NADP⁺ => 7-oxoglycolithocholate + NADPH + H⁺
RHEA:64417
D-xylofuranose + NADP⁺ => D-xylono-1,4-lactone + NADPH + H⁺
RHEA:63506
13-dihydrodaunorubicin + NADP⁺ => daunorubicin + NADPH + H⁺
RHEA:63481
prostaglandin F_2α + NADP⁺ => 15-oxoprostaglandin F_2α + NADPH + H⁺
RHEA:63477
prostaglandin E₂ + NADP⁺ => 15-oxoprostaglandin E₂ + NADPH + H⁺
RHEA:62269
(R)-2-hydroxy-3-methylbutanoate + NADP⁺ => 3-methyl-2-oxobutanoate + NADPH + H⁺
RHEA:62217
isoepoxydon + NADP⁺ => phyllostine + NADPH + H⁺
RHEA:62069
2-deoxy-D-glucose 6-phosphate + NADP⁺ => 2-deoxy-6-phospho-D-glucono-1,5-lactone + NADPH + H⁺
RHEA:56285
a (3R,4R)-4,2'-dihydroxyisoflavan + NADP⁺ => a (3R)-2'-hydroxyisoflavanone + NADPH + H⁺
RHEA:54445
a (2R,3S,4S)-leucoanthocyanidin + NADP⁺ => a (2R,3R)-dihydroflavonol + NADPH + H⁺
RHEA:53821
chenodeoxycholate + NADP⁺ => 7-oxolithocholate + NADPH + H⁺
RHEA:47542
ursodeoxycholate + NADP⁺ => 7-oxolithocholate + NADPH + H⁺
RHEA:45318
11β-prostaglandin F₂ + NADP⁺ => prostaglandin D₂ + NADPH + H⁺
RHEA:45117
(4R)-ipsdienol + NADP⁺ => ipsdienone + NADPH + H⁺
RHEA:42769
a (2S)-2-hydroxycarboxylate + NADP⁺ => a 2-oxocarboxylate + NADPH + H⁺
RHEA:42501
(6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + NADP⁺ => 6-lactoyl-5,6,7,8-tetrahydropterin + NADPH + H⁺
RHEA:36588
an aldopyranose + NADP⁺ => aldono-1,5-lactone + NADPH + H⁺
RHEA:35608
acetoin + NADP⁺ => diacetyl + NADPH + H⁺
RHEA:34788
a 3β-hydroxysteroid + NADP⁺ => a 3-oxosteroid + NADPH + H⁺
RHEA:34784
a 3α-hydroxysteroid + NADP⁺ => a 3-oxosteroid + NADPH + H⁺
RHEA:32620
L-threo-7,8-dihydrobiopterin + NADP⁺ => sepiapterin + NADPH + H⁺
RHEA:32340
(+)-thujan-3-ol + NADP⁺ => (+)-thujan-3-one + NADPH + H⁺
RHEA:31892
2-hydroxy-1-phenyl-1-propanone + NADP⁺ => 1-phenyl-1,2-propanedione + NADPH + H⁺
RHEA:25961
benzoin + NADP⁺ => benzil + NADPH + H⁺
RHEA:24509
prostaglandin F_2α + NADP⁺ => prostaglandin E₂ + NADPH + H⁺
RHEA:21793
propan-2-ol + NADP⁺ => acetone + NADPH + H⁺
RHEA:21749
(S)-lactaldehyde + NADP⁺ => methylglyoxal + NADPH + H⁺
RHEA:20745
prostaglandin D₂ + NADP⁺ => 15-oxoprostaglandin D₂ + NADPH + H⁺
RHEA:20234
a 7β-hydroxysteroid + NADP⁺ => a 7-oxosteroid + NADPH + H⁺
RHEA:18954
L-erythro-7,8-dihydrobiopterin + NADP⁺ => sepiapterin + NADPH + H⁺
RHEA:18942
a (3R,4R)-3-[(1S)-1-hydroxyalkyl]-4-(hydroxymethyl)oxolan-2-one + NADP⁺ => a (3R,4R)-3-alkanoyl-4-(hydroxymethyl)oxolan-2-one + NADPH + H⁺
RHEA:18426
L-quinate + NADP⁺ => 3-dehydroquinate + NADPH + H⁺
RHEA:18006
D-threitol + NADP⁺ => D-erythrulose + NADPH + H⁺
RHEA:17738
shikimate + NADP⁺ => 3-dehydroshikimate + NADPH + H⁺
RHEA:17026
xylitol + NADP⁺ => L-xylulose + NADPH + H⁺
RHEA:16818
6-phospho-D-gluconate + NADP⁺ => 6-phospho-2-dehydro-D-gluconate + NADPH + H⁺
RHEA:16322
(S)-indan-1-ol + NADP⁺ => indan-1-one + NADPH + H⁺
RHEA:15858
(17R,20S)-17,20-dihydroxypregn-4-en-3-one + NADP⁺ => 17α-hydroxyprogesterone + NADPH + H⁺
RHEA:13830
GDP-α-D-rhamnose + NADP⁺ => GDP-4-dehydro-α-D-rhamnose + NADPH + H⁺
RHEA:12213
9H-fluoren-9-ol + NADP⁺ => 9H-fluoren-9-one + NADPH + H⁺
RHEA:11773
6-lactoyl-5,6,7,8-tetrahydropterin + NADP⁺ => 6-pyruvoyl-5,6,7,8-tetrahydropterin + NADPH + H⁺
RHEA:10725
GDP-6-deoxy-α-D-talose + NADP⁺ => GDP-4-dehydro-α-D-rhamnose + NADPH + H⁺
RHEA:10141
prostaglandin F_2α + NADP⁺ => prostaglandin D₂ + NADPH + H⁺

Publications

Purification and properties of an NADPH-dependent carbonyl reductase from human brain. Relationship to prostaglandin 9-ketoreductase and xenobiotic ketone reductase.

Wermuth B.

A nonspecific NADPH-dependent carbonyl reductase from human brain (formerly designated as aldehyde reductase 1; Ris, M. M., and von Wartburg, J. P. (1973) Eur. J. Biochem. 37, 69-77) has been purified to homogeneity. The enzyme reduces a number of biologically and pharmacologically active carbonyl ... >> More

A nonspecific NADPH-dependent carbonyl reductase from human brain (formerly designated as aldehyde reductase 1; Ris, M. M., and von Wartburg, J. P. (1973) Eur. J. Biochem. 37, 69-77) has been purified to homogeneity. The enzyme reduces a number of biologically and pharmacologically active carbonyl compounds. Quinones, e.g. menadione, ubiquinone, and tocopherolquinone are the best substrates, followed by aldehydes containing an activated carbonyl moiety, e.g. 4-nitrobenzaldehyde or methylglyoxal. The enzyme also reduces ketones, e.g. prostaglandins of the E and A class, the anthracycline antibiotic daunorubicin and 3-ketosteroids. During catalysis the pro 4S hydrogen atom of the nicotinamide ring of NADPH is transferred to the substrate. Flavonoids, e.g. quercetin and rutin, indomethacin, ethacrynic acid, and dicoumarol inhibit the enzyme activity. 4-Hydroxymercuribenzoate and iodoacetate inactivate the enzyme. NADPH and substrate do not protect against the loss of activity. Carbonyl reductase consists of a single polypeptide chain with a molecular weight of 30,000. The native enzyme occurs in three molecular forms with similar substrate specificity and inhibitor sensitivity. The isoelectric points of the three enzyme species are 6.95, 7.85, and 8.5. In the presence of coenzyme the isoelectric points are shifted to 5.2 to 5.9. The comparison of structural and enzymic features of carbonyl reductase with other monomeric oxidoreductases suggests a close relationship of carbonyl reductase with prostaglandin 9-keto-reductase and xenobiotic ketone reductase. << Less

J. Biol. Chem. 256:1206-1213(1981) [PubMed] [EuropePMC]

This publication is cited by 3 other entries.
Heterogeneity of anthracycline antibiotic carbonyl reductases in mammalian livers.

Ahmed N.K., Felsted R.L., Bachur N.R.

Biochem Pharmacol 27:2713-2719(1978) [PubMed] [EuropePMC]

RHEA:19258 a secondary alcohol + NADP(+) => a ketone + NADPH + H(+) Reaction with net flow from left to right. help_outline

Enzymes

Reaction participants Show >> << Hide

Cross-references

Related reactions help_outline

Specific form(s) of this reaction

Publications

Purification and properties of an NADPH-dependent carbonyl reductase from human brain. Relationship to prostaglandin 9-ketoreductase and xenobiotic ketone reductase.

Heterogeneity of anthracycline antibiotic carbonyl reductases in mammalian livers.

RHEA:19258 a secondary alcohol + NADP(+) => a ketone + NADPH + H(+) Reaction with net flow from left to right. ^help_outline

Related reactions ^help_outline