Page last updated: 2024-10-24
(3R)-3-hydroxymyristoyl-[acyl-carrier-protein] dehydratase activity
Definition
Target type: molecularfunction
Catalysis of the reaction: (3R)-3-hydroxytetradecanoyl-[acyl-carrier protein] = tetradecenoyl-[acyl-carrier protein] + H2O. [GOC:ai, PMID:12368867, RHEA:41892]
**(3R)-3-hydroxymyristoyl-[acyl-carrier-protein] dehydratase activity** catalyzes the removal of a water molecule from (3R)-3-hydroxymyristoyl-[acyl-carrier-protein], a key step in the biosynthesis of unsaturated fatty acids. This reaction is a dehydration, specifically a trans-enoyl-CoA hydratase activity. The enzyme facilitates the conversion of a hydroxyl group at the beta position of a fatty acyl chain to a double bond. The enzyme's active site contains a catalytic cysteine residue that forms a covalent adduct with the substrate. This adduct facilitates the removal of the water molecule, resulting in the formation of a trans-double bond. The reaction requires a cofactor, typically a divalent metal ion such as magnesium or manganese, to stabilize the catalytic cysteine and promote substrate binding.'
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Proteins (2)
| Protein | Definition | Taxonomy |
|---|---|---|
| Fatty acid synthase | A fatty acid synthase that is encoded in the genome of chicken. [OMA:P12276, PRO:DNx] | Gallus gallus (chicken) |
| Fatty acid synthase | A fatty acid synthase that is encoded in the genome of human. [PRO:DNx, UniProtKB:P49327] | Homo sapiens (human) |
Compounds (35)
| Compound | Definition | Classes | Roles |
|---|---|---|---|
| lansoprazole | Lansoprazole: A 2,2,2-trifluoroethoxypyridyl derivative of timoprazole that is used in the therapy of STOMACH ULCERS and ZOLLINGER-ELLISON SYNDROME. The drug inhibits H(+)-K(+)-EXCHANGING ATPASE which is found in GASTRIC PARIETAL CELLS. Lansoprazole is a racemic mixture of (R)- and (S)-isomers. | benzimidazoles; pyridines; sulfoxide | anti-ulcer drug; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor |
| omeprazole | 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole : A member of the class of benzimidazoles that is 1H-benzimidazole which is substituted by a [4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl group at position 2 and a methoxy group at position 5. omeprazole : A racemate comprising equimolar amounts of (R)- and (S)-omeprazole. Omeprazole: A 4-methoxy-3,5-dimethylpyridyl, 5-methoxybenzimidazole derivative of timoprazole that is used in the therapy of STOMACH ULCERS and ZOLLINGER-ELLISON SYNDROME. The drug inhibits an H(+)-K(+)-EXCHANGING ATPASE which is found in GASTRIC PARIETAL CELLS. | aromatic ether; benzimidazoles; pyridines; sulfoxide | |
| pantoprazole | pantoprazole : A member of the class of benzimidazoles that is 1H-benzimidazole substituted by a difluoromethoxy group at position 5 and a [(3,4-dimethoxypyridin-2-yl)methyl]sulfinyl group at position 2. Pantoprazole: 2-pyridinylmethylsulfinylbenzimidazole proton pump inhibitor that is used in the treatment of GASTROESOPHAGEAL REFLUX and PEPTIC ULCER. | aromatic ether; benzimidazoles; organofluorine compound; pyridines; sulfoxide | anti-ulcer drug; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; environmental contaminant; xenobiotic |
| rabeprazole | Rabeprazole: A 4-(3-methoxypropoxy)-3-methylpyridinyl derivative of timoprazole that is used in the therapy of STOMACH ULCERS and ZOLLINGER-ELLISON SYNDROME. The drug inhibits H(+)-K(+)-EXCHANGING ATPASE which is found in GASTRIC PARIETAL CELLS. | benzimidazoles; pyridines; sulfoxide | anti-ulcer drug; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor |
| methionine | methionine : A sulfur-containing amino acid that is butyric acid bearing an amino substituent at position 2 and a methylthio substituent at position 4. Methionine: A sulfur-containing essential L-amino acid that is important in many body functions. | aspartate family amino acid; L-alpha-amino acid; methionine; methionine zwitterion; proteinogenic amino acid | antidote to paracetamol poisoning; human metabolite; micronutrient; mouse metabolite; nutraceutical |
| 3-hydroxyflavone | 3-hydroxyflavone: structure given in first source flavonol : A monohydroxyflavone that is the 3-hydroxy derivative of flavone. | flavonols; monohydroxyflavone | |
| dimethyl disulfide | organic disulfide | xenobiotic metabolite | |
| diallyl trisulfide | organic trisulfide | anti-inflammatory agent; antilipemic drug; antineoplastic agent; antioxidant; antiprotozoal drug; apoptosis inducer; estrogen receptor antagonist; insecticide; platelet aggregation inhibitor; vasodilator agent | |
| diallyl disulfide | diallyl disulfide : An organic disulfide where the organic group specified is allyl. It has been isolated from garlic and other species of the genus Allium. diallyl disulfide: major constituent of garlic oil | organic disulfide | antifungal agent; antineoplastic agent; plant metabolite |
| ursolic acid | hydroxy monocarboxylic acid; pentacyclic triterpenoid | geroprotector; plant metabolite | |
| epigallocatechin gallate | (-)-epigallocatechin 3-gallate : A gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin. epigallocatechin gallate: a steroid 5alpha-reductase inhibitor and antimutagen in green tea (Camellia sinensis) | flavans; gallate ester; polyphenol | antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite |
| epicatechin | (-)-epicatechin : A catechin with (2R,3R)-configuration. | catechin; polyphenol | antioxidant |
| epicatechin gallate | (-)-epicatechin-3-O-gallate : A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of epicatechin. A natural product found in Parapiptadenia rigida. epicatechin gallate: a steroid 5alpha-reductase inhibitor; RN given refers to the (cis)-isomer; structure given in first source; isolated from green tea | catechin; gallate ester; polyphenol | EC 3.2.1.1 (alpha-amylase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; metabolite |
| (+)-epicatechin | (+)-epicatechin : A catechin that is flavan carrying five hydroxy substituents at positions 3, 3', 4', 5 and 7 (the 2S,3S-stereoisomer). | catechin; polyphenol | cyclooxygenase 1 inhibitor; plant metabolite |
| s-adenosylhomocysteine | S-adenosyl-L-homocysteine : An organic sulfide that is the S-adenosyl derivative of L-homocysteine. S-Adenosylhomocysteine: 5'-S-(3-Amino-3-carboxypropyl)-5'-thioadenosine. Formed from S-adenosylmethionine after transmethylation reactions. | adenosines; amino acid zwitterion; homocysteine derivative; homocysteines; organic sulfide | cofactor; EC 2.1.1.72 [site-specific DNA-methyltransferase (adenine-specific)] inhibitor; EC 2.1.1.79 (cyclopropane-fatty-acyl-phospholipid synthase) inhibitor; epitope; fundamental metabolite |
| 5'-methylthioadenosine | 5'-methylthioadenosine: structure 5'-S-methyl-5'-thioadenosine : Adenosine with the hydroxy group at C-5' substituted with a methylthio (methylsulfanyl) group. | thioadenosine | algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite |
| egonol | egonol : A member of the class of 1-benzofurans that is 1-benzofuran substituted by a methoxy group at position 7, a 1,3-benzodioxol-5-yl group at position 2 and a 3-hydroxypropyl group at position 5. It has been isolated from Styrax agrestis. | 1-benzofurans; aromatic ether; benzodioxoles; primary alcohol | plant metabolite |
| orlistat | orlistat : A carboxylic ester resulting from the formal condensation of the carboxy group of N-formyl-L-leucine with the hydroxy group of (3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one. A pancreatic lipase inhibitor, it is used as an anti-obesity drug. Orlistat: A lactone derivative of LEUCINE that acts as a pancreatic lipase inhibitor to limit the absorption of dietary fat; it is used in the management of obesity. | beta-lactone; carboxylic ester; formamides; L-leucine derivative | anti-obesity agent; bacterial metabolite; EC 2.3.1.85 (fatty acid synthase) inhibitor; EC 3.1.1.3 (triacylglycerol lipase) inhibitor |
| luteolin | 3'-hydroxyflavonoid; tetrahydroxyflavone | angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; apoptosis inducer; c-Jun N-terminal kinase inhibitor; EC 2.3.1.85 (fatty acid synthase) inhibitor; immunomodulator; nephroprotective agent; plant metabolite; radical scavenger; vascular endothelial growth factor receptor antagonist | |
| gentisein | gentisein : A member of the class of xanthones that is 9H-xanthen-9-one substituted by hydroxy groups at positions 1, 3 and 7. gentisein: isolated from the methanol extract of the herb of Hypericum annulatum; structure in first source | polyphenol; xanthones | plant metabolite |
| mangostin | alpha-mangostin : A member of the class of xanthones that is 9H-xanthene substituted by hydroxy group at positions 1, 3 and 6, a methoxy group at position 7, an oxo group at position 9 and prenyl groups at positions 2 and 8. Isolated from the stems of Cratoxylum cochinchinense, it exhibits antioxidant, antimicrobial and antitumour activities. mangostin: xanthone from rind of Garcinia mangostana Linn. fruit | aromatic ether; phenols; xanthones | antimicrobial agent; antineoplastic agent; antioxidant; plant metabolite |
| norathyriol | norathyriol : A member of the class of xanthones that is 9H-xanthen-9-one substituted by hydroxy groups at positions 1, 3, 6 and 7. Isolated from Garcinia mangostana and Maclura pomifera, it exhibits inhibitory activity against protein kinase C. norathyriol: from Gentinanaceae; has vasorelaxing action on rat thoracic aorta; structure given in first source | polyphenol; xanthones | antineoplastic agent; EC 2.7.11.13 (protein kinase C) inhibitor; plant metabolite |
| ginkgolic acid | hydroxybenzoic acid | ||
| cerulenin | cerulenin : An epoxydodecadienamide isolated from several species, including Acremonium, Acrocylindrum and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function. Cerulenin: An epoxydodecadienamide isolated from several species, including ACREMONIUM, Acrocylindrum, and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function. | epoxide; monocarboxylic acid amide | antifungal agent; antiinfective agent; antilipemic drug; antimetabolite; antimicrobial agent; fatty acid synthesis inhibitor |
| trans-10,cis-12-conjugated linoleic acid | (10E,12Z)-octadecadienoic acid : An octadeca-10,12-dienoic acid having (10E,12Z)-configuration. | octadeca-10,12-dienoic acid | |
| gamma-mangostin | gamma-mangostin : A member of the class of xanthones that is 9H-xanthene substituted by hydroxy group at positions 1, 3, 6 and 7, an oxo group at position 9 and prenyl groups at positions 2 and 8. Isolated from the stems of Cratoxylum cochinchinense, it exhibits antitumour activity. | phenols; xanthones | antineoplastic agent; plant metabolite; protein kinase inhibitor |
| avicularin | avicularin : A quercetin O-glycoside in which an alpha-L-arabinofuranosyl residue is attached at position 3 of quercetin via a glycosidic linkage. It is isolated particularly from Juglans regia and Foeniculum vulgare. avicularin: from Polygonum aviculare L.; RN given refers to L-isomer | alpha-L-arabinofuranoside; monosaccharide derivative; quercetin O-glycoside; tetrahydroxyflavone | hepatoprotective agent; plant metabolite |
| beta-Mangostin | xanthones | ||
| 9-Hydroxycalabaxanthone | xanthones | ||
| 4-methylene-2-octyl-5-oxofuran-3-carboxylic acid | (2R,3S)-C75 : A 4-methylidene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid that has 2R,3S-configuration. 4-methylene-2-octyl-5-oxofuran-3-carboxylic acid: an anorectic fatty acid synthase inhibitor; structure in first source | 4-methylidene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid; gamma-lactone | |
| garcinone e | garcinone E: has potent cytotoxic effect against hepatocellular carcinoma cell lines; structure in first source | xanthones | |
| omdm 169 | OMDM 169: has antinociceptive activity; structure in first source | ||
| gsk837149a | GSK837149A: structure in first source | ||
| gsk2194069 | GSK2194069: a beta-ketoacyl reductase inhibitor; structure in first source | ||
| thiolactomycin | thiolactomycin: from actinomycetes; structure given in first source |