Rhea - reaction knowledgebase

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Name ^help_outline 5-dehydroepisterol Identifier CHEBI:52972 (Beilstein: 5128637) ^help_outline Charge 0 Formula C28H44O InChIKey^help_outline ZEPNVCGPJXYABB-LOIOQLKMSA-N SMILES^help_outline [H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=C)C(C)C 2D coordinates Mol file for the small molecule Search links Involved in 5 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 9,431 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 1,279 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 2,709 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline ergosta-5,7,22,24(28)-tetraen-3β-ol Identifier CHEBI:18249 (Beilstein: 2397531) ^help_outline Charge 0 Formula C28H42O InChIKey^help_outline SQFQJKZSFOZDJY-CVGLIYDESA-N SMILES^help_outline [H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)\C=C\C(=C)C(C)C 2D coordinates Mol file for the small molecule Search links Involved in 4 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 6,204 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 1,285 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule

Cross-references

	RHEA:33467	RHEA:33468	RHEA:33469	RHEA:33470
Reaction direction	undefined	left-to-right	right-to-left	bidirectional
UniProtKB ^help_outline	574 proteins	6 proteins
EC numbers ^help_outline	1.14.19.41
KEGG ^help_outline				R07506
MetaCyc ^help_outline		RXN3O-227

Publications

Purification and reconstitution of activity of Saccharomyces cerevisiae P450 61, a sterol delta 22-desaturase.

Kelly S.L., Lamb D.C., Corran A.J., Baldwin B.C., Parks L.W., Kelly D.E.

P450 was purified from microsomal fractions of a strain of Saccharomyces cerevisiae which contained detectable P450 despite the disruption of CYP51A1. The P450 had a molecular mass of 58 kDa, similar to P450 51A1, and in a reconstituted assay with rabbit NADPH-P450 reductase and dilauryl phosphoti ... >> More

P450 was purified from microsomal fractions of a strain of Saccharomyces cerevisiae which contained detectable P450 despite the disruption of CYP51A1. The P450 had a molecular mass of 58 kDa, similar to P450 51A1, and in a reconstituted assay with rabbit NADPH-P450 reductase and dilauryl phosphotidylcholine exhibited activity for conversion of ergosta-5,7-dienol into ergosterol. N-Terminal amino acid sequencing of the purified protein corresponded to the translated sequence of P450 61 which was recently identified during sequencing of chromosome XIII. This allowed the function of this family of P450 to be identified as sterol delta 22-desaturation in the pathway of ergosterol biosynthesis. << Less

FEBS Lett. 377:217-220(1995) [PubMed] [EuropePMC]
Interactions of the ergosterol biosynthetic pathway with other lipid pathways.

Veen M., Lang C.

Micro-organisms have recently received broad attention as sources of novel lipids. An increased understanding of the effects of fats and oils and their composition on the metabolism and on health has shifted the focus towards the use of lipids for disease treatment and prevention and for the promo ... >> More

Micro-organisms have recently received broad attention as sources of novel lipids. An increased understanding of the effects of fats and oils and their composition on the metabolism and on health has shifted the focus towards the use of lipids for disease treatment and prevention and for the promotion of good health. A large range of lipidic products produced by yeast is known today. Ergosterol and its metabolic precursors are major lipidic components of industrial and commercial interest. Having in mind the aim to increase the productivity of ergosterol and its precursor metabolites, both the knowledge of regulatory mechanisms of the biosynthetic pathway and its interactions with other lipid pathways like those of sphingolipids, phospholipids and fatty acids are crucial. << Less

Biochem Soc Trans 33:1178-1181(2005) [PubMed] [EuropePMC]

This publication is cited by 9 other entries.
Cloning and characterization of the Saccharomyces cerevisiae C-22 sterol desaturase gene, encoding a second cytochrome P-450 involved in ergosterol biosynthesis.

Skaggs B.A., Alexander J.F., Pierson C.A., Schweitzer K.S., Chun K.T., Koegel C., Barbuch R., Bard M.

The ERG5 gene from Saccharomyces cerevisiae was cloned by complementation of an erg5-1 mutation using a negative selection protocol involving screening for nystatin-sensitive transformants. ERG5 is the putative gene encoding the C-22 sterol desaturase required in ergosterol biosynthesis. The funct ... >> More

The ERG5 gene from Saccharomyces cerevisiae was cloned by complementation of an erg5-1 mutation using a negative selection protocol involving screening for nystatin-sensitive transformants. ERG5 is the putative gene encoding the C-22 sterol desaturase required in ergosterol biosynthesis. The functional gene was localized to a 2.15-kb SacI-EcoRI DNA fragment containing an open reading frame of 538 amino acids (aa). ERG5 contains a 10-aa motif consistent with its role as a cytochrome P-450 (CyP450) enzyme and is similar to a number of mammalian CyP450 enzymes. Gene disruption demonstrates that ERG5 is not essential for cell viability. << Less

Gene 169:105-109(1996) [PubMed] [EuropePMC]

RHEA:33469 ergosta-5,7,22,24(28)-tetraen-3beta-ol + 2 H2O + NADP(+) => 5-dehydroepisterol + H(+) + NADPH + O2 Reaction with net flow from right to left. help_outline

Reaction participants Show >> << Hide

Cross-references

Publications

Purification and reconstitution of activity of Saccharomyces cerevisiae P450 61, a sterol delta 22-desaturase.

Interactions of the ergosterol biosynthetic pathway with other lipid pathways.

Cloning and characterization of the Saccharomyces cerevisiae C-22 sterol desaturase gene, encoding a second cytochrome P-450 involved in ergosterol biosynthesis.

RHEA:33469 ergosta-5,7,22,24(28)-tetraen-3beta-ol + 2 H2O + NADP(+) => 5-dehydroepisterol + H(+) + NADPH + O2 Reaction with net flow from right to left. ^help_outline