| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:07:54 -0700 |
| HMDB ID |
HMDB00108 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
Ethanol |
| Description |
Ethanol is a clear, colorless liquid rapidly absorbed from the gastrointestinal tract and distributed throughout the body. It has bactericidal activity and is used often as a topical disinfectant. It is widely used as a solvent and preservative in pharmaceutical preparations as well as serving as the primary ingredient in alcoholic beverages. Indeed, ethanol has widespread use as a solvent of substances intended for human contact or consumption, including scents, flavorings, colorings, and medicines. Ethanol has a depressive effect on the central nervous system and because of its psychoactive effects, it is considered a drug. Ethanol has a complex mode of action and affects multiple systems in the brain, most notably it acts as an agonist to the GABA receptors. Death from ethanol consumption is possible when blood alcohol level reaches 0.4%. A blood level of 0.5% or more is commonly fatal. Levels of even less than 0.1% can cause intoxication, with unconsciousness often occurring at 0.3-0.4 %. Ethanol is metabolized by the body as an energy-providing carbohydrate nutrient, as it metabolizes into acetyl CoA, an intermediate common with glucose metabolism, that can be used for energy in the citric acid cycle or for biosynthesis. Ethanol within the human body is converted into acetaldehyde by alcohol dehydrogenase and then into acetic acid by acetaldehyde dehydrogenase. The product of the first step of this breakdown, acetaldehyde, is more toxic than ethanol. Acetaldehyde is linked to most of the clinical effects of alcohol. It has been shown to increase the risk of developing cirrhosis of the liver,[77] multiple forms of cancer, and alcoholism. Industrially, ethanol is produced both as a petrochemical, through the hydration of ethylene, and biologically, by fermenting sugars with yeast. Small amounts of ethanol are endogenously produced by gut microflora through anaerobic fermentation. However most ethanol detected in biofluids and tissues likely comes from consumption of alcoholic beverages. Absolute ethanol or anhydrous alcohol generally refers to purified ethanol, containing no more than one percent water. Absolute alcohol is not intended for human consumption. It often contains trace amounts of toxic benzene (used to remove water by azeotropic distillation). Consumption of this form of ethanol can be fatal over a short time period. Generally absolute or pure ethanol is used as a solvent for lab and industrial settings where water will disrupt a desired reaction. Pure ethanol is classed as 200 proof in the USA and Canada, equivalent to 175 degrees proof in the UK system. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- 1-Hydroxyethane
- Absolute alcohol
- Absolute ethanol
- Absolute ethyl alcohol
- Aethanol
- Aethylalkohol
- Alcare Hand Degermer
- Alcohol
- Alcohols
- Alcool ethylique
- Alcool etilico
- Algrain
- Alkohol
- Alkoholu etylowego
- Anhydrol
- Anhydrous alcohol
- Cologne spirit
- Cologne spirits
- Dehydrated alcohol
- Dehydrated ethanol
- Denatured alcohol
- Denatured ethanol
- Desinfektol EL
- Diluted Alcohol
- Distilled spirits
- Ethanol 200 proof
- Ethanol solution
- Ethicap
- Ethyl alc
- Ethyl alcohol
- Ethyl alcohol anhydrous
- Ethyl alcohol in alcoholic beverages
- Ethyl alcohol usp
- Ethyl hydrate
- Ethyl hydroxide
- Fermentation alcohol
- Grain alcohol
- Hinetoless
- Hydroxyethane
- Infinity Pure
- Jaysol
- Jaysol S
- Lux
- Methylcarbinol
- Molasses alcohol
- Potato alcohol
- Punctilious ethyl alcohol
- Pyro
- Silent spirit
- Spirit
- Spirits of wine
- Spirt
- Synasol
- Tecsol
- Tecsol C
- Thanol
- Undenatured Ethanol
|
| Chemical Formula |
C2H6O |
| Average Molecular Weight |
46.0684 |
| Monoisotopic Molecular Weight |
46.041864814 |
| IUPAC Name |
ethanol |
| Traditional IUPAC Name |
ethyl alcohol |
| CAS Registry Number |
64-17-5 |
| SMILES |
CCO |
| InChI Identifier |
InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3 |
| InChI Key |
LFQSCWFLJHTTHZ-UHFFFAOYSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Aliphatic Acyclic Compounds |
| Class |
Alcohols and Polyols |
| Sub Class |
Primary Alcohols |
| Other Descriptors |
- Aliphatic Acyclic Compounds
- a primary alcohol(Cyc)
- a short-chain alcohol(Cyc)
- alkyl alcohol(ChEBI)
- ethanols(ChEBI)
- primary alcohol(ChEBI)
|
| Substituents |
|
| Direct Parent |
Primary Alcohols |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
- Component of Androgen and estrogen metabolism
- Component of Bile acid biosynthesis
- Component of C21-Steroid hormone metabolism
- Component of Fatty acid metabolism
- Component of Glycerolipid metabolism
- Component of Sulfur metabolism
- Component of Tyrosine metabolism
|
| Application |
Not Available |
| Cellular locations |
- Cytoplasm
- Extracellular
- Peroxisome
|
| Physical Properties |
|---|
| State |
Liquid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
-114.1 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
1000.0 mg/mL |
Not Available |
| LogP |
-0.31 |
HANSCH,C ET AL. (1995) |
|
| Predicted Properties |
|
| Spectra |
|---|
|
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| Biological Properties |
|---|
| Cellular Locations |
- Cytoplasm
- Extracellular
- Peroxisome
|
| Biofluid Locations |
- Blood
- Cerebrospinal Fluid (CSF)
- Saliva
- Urine
|
| Tissue Location |
- Muscle
- Skeletal Muscle
- Bladder
- Fibroblasts
- Intestine
- Neuron
- Pancreas
- Placenta
- Kidney
- Liver
- Epidermis
- Brain
- Myelin
- Prostate
- Adrenal Gland
- Fetus
- Adipose Tissue
- Adrenal Cortex
- Adrenal Medulla
- Lung
- Nerve Cells
- Platelet
- Gonads
- Gut
- Heart
- Mouth
|
| Pathways |
| Name |
SMPDB Link |
KEGG Link |
| Ethanol Degradation |
SMP00449
|
Not Available
|
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| Normal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
40.0 (0.0-80.0) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
15.0 (0.0-33.0) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Saliva |
Detected and Quantified |
|
>10 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
<0.01 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.0105 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
5-500 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Presence only detectable in urine within 3-4...
|
| Urine |
Detected and Quantified |
|
3.1 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
|
| Abnormal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
40.2 +/- 12.1 uM |
Adult (>18 years old) |
Not Specified |
Heart Transplant |
Not Available |
| Blood |
Detected and Quantified |
|
45393.0 (18027.0-74063.0) uM |
Adult (>18 years old) |
Both |
Alcohol intoxication |
Not Available |
| Blood |
Detected and Quantified |
|
40615.0 +/- 17158.0 uM |
Adult (>18 years old) |
Male |
Drunk driver |
Not Available |
| Blood |
Detected and Quantified |
|
90.0 (10.0-170.0) uM |
Adult (>18 years old) |
Both |
Kidney disease |
Chronic renal insufficiency
|
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
230 +/- 30 uM |
Adult (>18 years old) |
Not Specified |
Cervical myelopathy |
Not Available |
| Urine |
Detected and Quantified |
|
54.0 (0.0-661.0) umol/mmol creatinine |
Not Specified |
Both |
Lung cancer |
Not Available |
| Urine |
Detected and Quantified |
|
0.0039 - 0.0617 umol/mmol creatinine |
Adult (>18 years old) |
Both |
ADPKD |
Not Available |
| Urine |
Detected and Quantified |
|
3543.6 +/- 1414.6 umol/mmol creatinine |
Adult (>18 years old) |
Male |
Drunk driver |
Not Available |
|
| Associated Disorders and Diseases |
|---|
| Disease References |
| Cervical myelopathy |
|---|
- Meshitsuka S, Morio Y, Nagashima H, Teshima R: 1H-NMR studies of cerebrospinal fluid: endogenous ethanol in patients with cervical myelopathy. Clin Chim Acta. 2001 Oct;312(1-2):25-30.
Pubmed: 11580906
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| Lung Cancer |
|---|
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| Kidney disease |
|---|
- Liebich HM, Woll J: Volatile substances in blood serum: profile analysis and quantitative determination. J Chromatogr. 1977 Nov 11;142:505-16.
Pubmed: 914932
|
| Alcoholism |
|---|
- Jones AW, Lund M, Andersson E: Drinking drivers in Sweden who consume denatured alcohol preparations: an analytical-toxicological study. J Anal Toxicol. 1989 Jul-Aug;13(4):199-203.
Pubmed: 2779169
- Jones AW, Helander A: Changes in the concentrations of ethanol, methanol and metabolites of serotonin in two successive urinary voids from drinking drivers. Forensic Sci Int. 1998 May 11;93(2-3):127-34.
Pubmed: 9717263
|
| Abnormal |
|---|
- Schneider H, Glatt H: Sulpho-conjugation of ethanol in humans in vivo and by individual sulphotransferase forms in vitro. Biochem J. 2004 Nov 1;383(Pt. 3):543-9.
Pubmed: 15281911
|
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| Associated OMIM IDs |
|
| External Links |
|---|
| DrugBank ID |
DB00898 |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB000753 |
| KNApSAcK ID |
C00019560 |
| Chemspider ID |
682 |
| KEGG Compound ID |
C00469 |
| BioCyc ID |
ETOH |
| BiGG ID |
35062 |
| Wikipedia Link |
Ethanol |
| NuGOwiki Link |
HMDB00108 |
| Metagene Link |
HMDB00108 |
| METLIN ID |
3203 |
| PubChem Compound |
702 |
| PDB ID |
EOH |
| ChEBI ID |
16236 |
| References |
|---|
| Synthesis Reference |
Lashley, David. Process for producing an alcoholic sugar cane juice beverage. U.S. (1988), 3 pp. CODEN: USXXAM US 4784859 A 19881115 CAN 110:113222 AN 1989:113222 |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7.
Pubmed: 12097436
- Gordon Z, Parsons CL, Monga M: Intravesical ethanol test: an ineffective measure of bladder hyperpermeability. Urology. 2003 Mar;61(3):555-7.
Pubmed: 12639646
- Huang JS, She QB, Crilly KS, Kiss Z: Ethanol, Zn2+ and insulin interact as progression factors to enhance DNA synthesis synergistically in the presence of Ca2+ and other cell cycle initiators in fibroblasts. Biochem J. 2000 Feb 15;346 Pt 1:241-7.
Pubmed: 10657263
- Friedman GD, Klatsky AL, Siegelaub AB: Alcohol, tobacco, and hypertension. Hypertension. 1982 Sep-Oct;4(5 Pt 2):III143-50.
Pubmed: 7049929
- Uemura M, Lehmann WD, Schneider W, Seitz HK, Benner A, Keppler-Hafkemeyer A, Hafkemeyer P, Kojima H, Fujimoto M, Tsujii T, Fukui H, Keppler D: Enhanced urinary excretion of cysteinyl leukotrienes in patients with acute alcohol intoxication. Gastroenterology. 2000 Jun;118(6):1140-8.
Pubmed: 10833489
- Hemmingsen R, Barry DI, Hertz MM, Klinken L: Cerebral blood flow and oxygen consumption during ethanol withdrawal in the rat. Brain Res. 1979 Sep 14;173(2):259-69.
Pubmed: 573652
- Lopez JM, Bombi JA, Valderrama R, Gimenez A, Pares A, Caballeria J, Imperial S, Navarro S: Effects of prolonged ethanol intake and malnutrition on rat pancreas. Gut. 1996 Feb;38(2):285-92.
Pubmed: 8801213
- Yamashina S, Ikejima K, Enomoto N, Takei Y, Sato N: [Ethanol changes sensitivity of Kupffer cells to endotoxin] Nihon Arukoru Yakubutsu Igakkai Zasshi. 2003 Oct;38(5):415-24.
Pubmed: 14639920
- Aye MM, Ma C, Lin H, Bower KA, Wiggins RC, Luo J: Ethanol-induced in vitro invasion of breast cancer cells: the contribution of MMP-2 by fibroblasts. Int J Cancer. 2004 Dec 10;112(5):738-46.
Pubmed: 15386367
- De Martinis BS, de Paula CM, Braga A, Moreira HT, Martin CC: Alcohol distribution in different postmortem body fluids. Hum Exp Toxicol. 2006 Feb;25(2):93-7.
Pubmed: 16539214
- Pohorecky LA: Influence of alcohol on peripheral neurotransmitter function. Fed Proc. 1982 Jun;41(8):2452-5.
Pubmed: 6123447
- Dean RA, Zhang J, Brzezinski MR, Bosron WF: Tissue distribution of cocaine methyl esterase and ethyl transferase activities: correlation with carboxylesterase protein. J Pharmacol Exp Ther. 1995 Nov;275(2):965-71.
Pubmed: 7473189
- Elias AN, Meshkinpour H, Valenta LJ, Grossman MK: Pseudo-Cushing's syndrome: the role of alcohol. J Clin Gastroenterol. 1982 Apr;4(2):137-9.
Pubmed: 6282953
- Henriksson J, Knol M: A single bout of exercise is followed by a prolonged decrease in the interstitial glucose concentration in skeletal muscle. Acta Physiol Scand. 2005 Dec;185(4):313-20.
Pubmed: 16266372
- Rosdahl H, Lind L, Millgard J, Lithell H, Ungerstedt U, Henriksson J: Effect of physiological hyperinsulinemia on blood flow and interstitial glucose concentration in human skeletal muscle and adipose tissue studied by microdialysis. Diabetes. 1998 Aug;47(8):1296-301.
Pubmed: 9703331
- Boschmann M, Adams F, Schaller K, Franke G, Sharma AM, Klaus S, Luft FC, Jordan J: Hemodynamic and metabolic responses to interstitial angiotensin II in normal weight and obese men. J Hypertens. 2006 Jun;24(6):1165-71.
Pubmed: 16685217
- Igawa Y, Satoh T, Mizusawa H, Seki S, Kato H, Ishizuka O, Nishizawa O: The role of capsaicin-sensitive afferents in autonomic dysreflexia in patients with spinal cord injury. BJU Int. 2003 May;91(7):637-41.
Pubmed: 12699475
- Enocksson S, Shimizu M, Lonnqvist F, Nordenstrom J, Arner P: Demonstration of an in vivo functional beta 3-adrenoceptor in man. J Clin Invest. 1995 May;95(5):2239-45.
Pubmed: 7738189
- Collins JW, Macdermott S, Bradbrook RA, Keeley FX Jr, Timoney AG: Is using ethanol-glycine irrigating fluid monitoring and 'good surgical practice' enough to prevent harmful absorption during transurethral resection of the prostate? BJU Int. 2006 Jun;97(6):1247-51.
Pubmed: 16686720
- Sokolik VV, Chursina VS, Artemchuk AA, Artemchuk AF, Bozhko GKh: [Depression of serum esterase and lipoprotein lipase activities in acute and longitudinal actions of ethanol] Biomed Khim. 2006 Jan-Feb;52(1):95-100.
Pubmed: 16739925
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| Enzymes |
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| Name: |
Cytochrome P450 4A11
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| Reactions: |
- octane + reduced rubredoxin + O2 = 1-octanol + oxidized rubredoxin + H2O [RN:R02879]
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| Gene Name: |
CYP4A11 |
| Uniprot ID: |
Q02928 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Beta-glucuronidase
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| Reactions: |
- a beta-D-glucuronoside + H2O = D-glucuronate + an alcohol [RN:R01478]
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| Gene Name: |
GUSB |
| Uniprot ID: |
P08236 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytochrome P450 3A4
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| Reactions: |
- (1) taurochenodeoxycholate + NADPH + H+ + O2 = taurohyocholate + NADP+ + H2O [RN:R07205]
- (2) lithocholate + NADPH + H+ + O2 = hyodeoxycholate + NADP+ + H2O [RN:R07206]
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| Gene Name: |
CYP3A4 |
| Uniprot ID: |
P08684 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytochrome P450 2C9
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| Reactions: |
- (R)-limonene + NADPH + H+ + O2 = (+)-trans-carveol + NADP+ + H2O [RN:R06119]
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| Gene Name: |
CYP2C9 |
| Uniprot ID: |
P11712 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytochrome P450 2C19
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| Reactions: |
- (R)-limonene + NADPH + H+ + O2 = (+)-trans-carveol + NADP+ + H2O [RN:R06119]
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| Gene Name: |
CYP2C19 |
| Uniprot ID: |
P33261 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytochrome P450 2B6
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| Reactions: |
- RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
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| Gene Name: |
CYP2B6 |
| Uniprot ID: |
P20813 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytochrome P450 1A1
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| Reactions: |
- RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
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| Gene Name: |
CYP1A1 |
| Uniprot ID: |
P04798 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytochrome P450 1A2
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| Reactions: |
- RH + reduced flavoprotein + O2 = ROH + oxidized flavoprotein + H2O [RN:R04122]
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| Gene Name: |
CYP1A2 |
| Uniprot ID: |
P05177 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Lecithin retinol acyltransferase
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| Reactions: |
- phosphatidylcholine + retinol---[cellular-retinol-binding-protein] = 2-acylglycerophosphocholine + retinyl-ester---[cellular-retinol-binding-protein] [RN:R04514]
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| Gene Name: |
LRAT |
| Uniprot ID: |
O95237 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Klotho
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| Reactions: |
- a beta-D-glucuronoside + H2O = D-glucuronate + an alcohol [RN:R01478]
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| Gene Name: |
KL |
| Uniprot ID: |
Q9UEF7 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Carboxylesterase 7
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| Reactions: |
- a carboxylic ester + H2O = an alcohol + a carboxylate [RN:R00630]
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| Gene Name: |
CES7 |
| Uniprot ID: |
Q6NT32 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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