Rhea - reaction knowledgebase

Enzymes

UniProtKB ^help_outline	1 proteins
Enzyme classes ^help_outline	EC 1.14.14.89 4'-methoxyisoflavone 2'-hydroxylase EC 1.14.14.90 isoflavone 2'-hydroxylase
GO Molecular Function ^help_outline	GO:0047957 4'-methoxyisoflavone 2'-hydroxylase activity

Reaction participants Show >> << Hide

Name ^help_outline formononetin Identifier CHEBI:77688 Charge -1 Formula C16H11O4 InChIKey^help_outline HKQYGTCOTHHOMP-UHFFFAOYSA-M SMILES^help_outline COc1ccc(cc1)-c1coc2cc([O-])ccc2c1=O 2D coordinates Mol file for the small molecule Search links Involved in 3 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline O₂ Identifier CHEBI:15379 (CAS: 7782-44-7) ^help_outline Charge 0 Formula O2 InChIKey^help_outline MYMOFIZGZYHOMD-UHFFFAOYSA-N SMILES^help_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
Name^help_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 InChIKey^help_outline YTNIXZGTHTVJBW-SCRDCRAPSA-L SMILES^help_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
Search links Involved in 711 reaction(s) Find proteins in UniProtKB for this molecule
Name ^help_outline 2'-hydroxyformononetin Identifier CHEBI:77687 Charge -1 Formula C16H11O5 InChIKey^help_outline XKHHKXCBFHUOHM-UHFFFAOYSA-M SMILES^help_outline COc1ccc(c(O)c1)-c1coc2cc([O-])ccc2c1=O 2D coordinates Mol file for the small molecule Search links Involved in 2 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 9,176 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 InChIKey^help_outline XLYOFNOQVPJJNP-UHFFFAOYSA-N SMILES^help_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
Name^help_outline oxidized [NADPH—hemoprotein reductase] Identifier RHEA-COMP:11965 Reactive part ^help_outline
- Name ^help_outline FMN Identifier CHEBI:58210 Charge -3 Formula C17H18N4O9P InChIKey^help_outline ANKZYBDXHMZBDK-SCRDCRAPSA-K SMILES^help_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
Search links Involved in 711 reaction(s) Find proteins in UniProtKB for this molecule

Cross-references

	RHEA:12388	RHEA:12389	RHEA:12390	RHEA:12391
Reaction direction	undefined	left-to-right	right-to-left	bidirectional
UniProtKB ^help_outline	1 proteins
EC numbers ^help_outline	1.14.14.89 1.14.14.90
Gene Ontology ^help_outline	GO:0047957
KEGG ^help_outline				R06560
MetaCyc ^help_outline		ISOFLAVONE-2-HYDROXYLASE-RXN

Related reactions ^help_outline

More general form(s) of this reaction

RHEA:18849
a 2ʼ-unsubstituted isoflavone + O₂ + reduced [NADPH—hemoprotein reductase] = a 2'-hydroxyisoflavone + H⁺ + H₂O + oxidized [NADPH—hemoprotein reductase]

Publications

Regiospecific hydroxylation of isoflavones by cytochrome P450 81E enzymes from Medicago truncatula.

Liu C.J., Huhman D., Sumner L.W., Dixon R.A.

Mining of Medicago truncatula EST databases and screening of a root cDNA library led to the identification of three cytochrome p450 81E subfamily members. Two were functionally characterized by expression in yeast. The recombinant enzymes in yeast microsomes utilized the same isoflavone substrates ... >> More

Mining of Medicago truncatula EST databases and screening of a root cDNA library led to the identification of three cytochrome p450 81E subfamily members. Two were functionally characterized by expression in yeast. The recombinant enzymes in yeast microsomes utilized the same isoflavone substrates, but produced different products hydroxylated at the 2' and/or 3' positions of the B-ring. When transiently expressed in alfalfa leaves, green fluorescent protein (GFP) fusions of the isoflavone 2'- and 3'-hydroxylases localized to the endoplasmic reticulum. The isoflavone 2'-hydroxylase was functional when expressed in Arabidopsis. Differential tissue-specific and biotic/abiotic stress-dependent expression patterns were observed for the isoflavone 2'-hydroxylase and 3'-hydroxylase genes, suggesting differential involvement of 2'- and 3'-hydroxylated isoflavonoids in pathogen defense and insect-induced responses, respectively, in Medicago. << Less

Plant J. 36:471-484(2003) [PubMed] [EuropePMC]

This publication is cited by 1 other entry.

Comments

Published in: Hinderer, W., Flentje, U. and Barz, W. Microsomal isoflavone 2′-hydroxylases and 3′-hydroxylases from chickpea (Cicer arietinum L) cell-suspensions induced for pterocarpan phytoalexin formation. FEBS Lett. 214 (1987) 101–106.