cis-5,8,11,14,17-Eicosapentaenoic acid - ≥95%, high purity , CAS No.10417-94-4

Item Number
E122277
Grouped product items
SKUSizeAvailabilityPrice Qty
E122277-25mg
25mg
Available within 4-8 weeks(?)
Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!
$28.90
E122277-100mg
100mg
Available within 4-8 weeks(?)
Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!
$89.90
E122277-500mg
500mg
Available within 4-8 weeks(?)
Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!
$249.90
E122277-1g
1g
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Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!
$389.90
E122277-5g
5g
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$1,299.90
E122277-25g
25g
Available within 4-8 weeks(?)
Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!
$4,499.90

Basic Description

SynonymsEPA | all cis-5,8,11,14,17-Eicosapentaenoic Acid | all cis-5,8,11,14,17-Icosapentaenoic Acid
Specifications & PurityMoligand™, ≥95%
Biochemical and Physiological Mechanisms5-Lipoxygenase inhibitor; reduces thromboxane A2 production.
Storage TempStore at -20°C,Argon charged
Shipped InIce chest + Ice pads
GradeMoligand™
Product Description

Eicosapentaenoic acid is a polyunsaturated fatty acid (PUFAs) and is synthesized from linolenic acid. It is distributed in phospholipid bilayers of the cell membrane, synaptic membranes of the brain and retina.It is obtained majorly from fish oil, seaweed, phytoplankton, and camelina.Being an Omega-3 fatty acid, it shows cis-trans conformations.

cis-5,8,11,14,17-Eicosapentaenoic acid has been used:

· to test pharmacologic effect on steatosis in hepatocytes

· as an analytical standard in Raman spectra measurements to characterize human breast cancer samples

· in lipid peroxidation assay in mouse embryonic fibroblasts and in pre-treatment of cells for cell viability studies

Product Properties

ALogP5.6

Associated Targets(Human)

F2 Tclin Thrombin (11687 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ESR1 Tclin Estrogen receptor alpha (17718 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PGR Tclin Progesterone receptor (8562 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AR Tclin Androgen Receptor (11781 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
VDR Tclin Vitamin D receptor (26531 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP19A1 Tclin Cytochrome P450 19A1 (6099 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAOA Tclin Monoamine oxidase A (11911 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD1 Tclin Dopamine D1 receptor (9720 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ACHE Tclin Acetylcholinesterase (18204 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC6A2 Tclin Norepinephrine transporter (10102 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC6A4 Tclin Serotonin transporter (12625 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OPRM1 Tclin Mu opioid receptor (19785 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD3 Tclin Dopamine D3 receptor (14368 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC6A3 Tclin Dopamine transporter (10535 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PPARA Tclin Peroxisome proliferator-activated receptor alpha (9197 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KCNH2 Tclin HERG (29587 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PDE3A Tclin Phosphodiesterase 3A (3309 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RXRA Tclin Retinoid X receptor alpha (3637 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PDE4A Tclin Phosphodiesterase 4A (1943 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADORA3 Tchem Adenosine A3 receptor (15931 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HRH3 Tclin Histamine H3 receptor (10389 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KDR Tclin Vascular endothelial growth factor receptor 2 (20924 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-MB-468 (9477 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCT-116 (91556 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
POLK Tbio DNA polymerase kappa (8653 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
POLL Tbio DNA polymerase lambda (184 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KMT2A Tchem Histone-lysine N-methyltransferase MLL (17327 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OXER1 Tchem Oxoeicosanoid receptor 1 (131 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RGS4 Tchem Regulator of G-protein signaling 4 (13867 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SREBF2 Tchem Sterol regulatory element-binding protein 2 (50 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
F7 Tchem Coagulation factor VII/tissue factor (740 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GLS Tchem Glutaminase kidney isoform, mitochondrial (16997 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EA.hy 926 (491 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Trypsin (394 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ppard Peroxisome proliferator-activated receptor delta (358 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Hepatitis C virus (23859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RAW264.7 (28094 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RBL-2H3 (1162 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SARS-CoV-2 (38078 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Names and Identifiers

IUPAC Name (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
INCHI InChI=1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15-
InChi Key JAZBEHYOTPTENJ-JLNKQSITSA-N
Canonical SMILES CCC=CCC=CCC=CCC=CCC=CCCCC(=O)O
Isomeric SMILES CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
WGK Germany 3
PubChem CID 446284
UN Number 3265
Molecular Weight 302.45
Beilstein 1714433

Certificates

Certificate of Analysis(COA)

Enter Lot Number to search for COA:

Find and download the COA for your product by matching the lot number on the packaging.

27 results found

Lot NumberCertificate TypeDateItem
J2422378Certificate of AnalysisSep 26, 2024 E122277
J2422377Certificate of AnalysisSep 26, 2024 E122277
J2422376Certificate of AnalysisSep 26, 2024 E122277
J2422374Certificate of AnalysisSep 26, 2024 E122277
J2422373Certificate of AnalysisSep 26, 2024 E122277
E2428596Certificate of AnalysisMay 09, 2024 E122277
E2428597Certificate of AnalysisMay 09, 2024 E122277
E2428609Certificate of AnalysisMay 09, 2024 E122277
E2428610Certificate of AnalysisMay 09, 2024 E122277
E2428611Certificate of AnalysisMay 09, 2024 E122277
C2407219Certificate of AnalysisFeb 26, 2024 E122277
C2407222Certificate of AnalysisFeb 26, 2024 E122277
A2425017Certificate of AnalysisOct 14, 2023 E122277
J2325268Certificate of AnalysisOct 14, 2023 E122277
J2325267Certificate of AnalysisOct 14, 2023 E122277
L2110072Certificate of AnalysisSep 12, 2023 E122277
G2326624Certificate of AnalysisJul 03, 2023 E122277
G2326641Certificate of AnalysisJul 03, 2023 E122277
A2104177Certificate of AnalysisApr 10, 2023 E122277
A2104181Certificate of AnalysisApr 10, 2023 E122277
F2411074Certificate of AnalysisNov 22, 2022 E122277
D2315708Certificate of AnalysisNov 22, 2022 E122277
D2315707Certificate of AnalysisNov 22, 2022 E122277
D2315697Certificate of AnalysisNov 22, 2022 E122277
A2104180Certificate of AnalysisOct 19, 2022 E122277
A2104178Certificate of AnalysisOct 19, 2022 E122277
A2104176Certificate of AnalysisOct 19, 2022 E122277

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Chemical and Physical Properties

SolubilitySoluble in methanol
SensitivityAir & Light & heat sensitive
Refractive Index1.4977
Flash Point(°F)199.4 °F
Flash Point(°C)93℃
Melt Point(°C)-54--53°C

Safety and Hazards(GHS)

Pictogram(s) GHS05
Signal Danger
Hazard Statements

H314:Causes severe skin burns and eye damage

Precautionary Statements

P280:Wear protective gloves/protective clothing/eye protection/face protection.

P321:Specific treatment (see ... on this label).

P405:Store locked up.

P501:Dispose of contents/container to ...

P264:Wash hands [and …] thoroughly after handling.

P260:Do not breathe dust/fume/gas/mist/vapors/spray.

P301+P330+P331:IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P304+P340:IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P363:Wash contaminated clothing before reuse.

P305+P354+P338:IF IN EYES: Immediately rinse with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.

P302+P361+P354:IF ON SKIN: Take off Immediately all contaminated clothing. Immediately rinse with water for several minutes.

P316:Get emergency medical help immediately.

WGK Germany 3
Merck Index 3531

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Citations of This Product

1. Lei Zhang, Peng Shi, Lin Zhang, Yajun Wang, Jilin Xu, Xiaojun Yan, Kai Liao.  (2023)  Molecular Characterization and Expression Response of Ghrelin, GLP-1 and PYY to Fasting, Dietary Lipid, and Fatty Acids in Silver Pomfret (Pampus argenteus).  Fishes,  (3): (170).  [PMID:] [10.3390/fishes8030170]
2. Xin-Nan Teng, Shu-Chang Wang, Liaqat Zeb, Yue-Sheng Dong, Zhi-Long Xiu.  (2023)  Two-Step Enzymolysis of Antarctic Krill for Simultaneous Preparation of Value-Added Oil and Enzymolysate.  Marine Drugs,  21  (1): (47).  [PMID:36662220] [10.3390/md21010047]
3. Jie Cheng, Yuling Li, Yunjun Wang, Jing Zhang, Tuanqi Sun, Li Zhang, Yinlong Guo.  (2022)  Quaterization Derivatization with Bis(Pyridine) Iodine Tetrafluoroboride: High-Sensitivity Mass Spectrometric Analysis of Unsaturated Fatty Acids in Human Thyroid Tissues.  ANALYTICAL CHEMISTRY,  94  (32): (11185–11191).  [PMID:35916214] [10.1021/acs.analchem.2c01519]
4. Baoping Xiao, Yuanyuan Li, Yanqi Lin, Jingyu Lin, Lingyu Zhang, Daren Wu, Jun Zeng, Jian Li, Jing wen Liu, Guiling Li.  (2022)  Eicosapentaenoic acid (EPA) exhibits antioxidant activity via mitochondrial modulation.  FOOD CHEMISTRY,  373  (131389).  [PMID:34710690] [10.1016/j.foodchem.2021.131389]
5. Wen Zhang, An Bu, Qingyuan Ji, Luofu Min, Song Zhao, Yuxin Wang, Jing Chen.  (2019)  pKa-Directed Incorporation of Phosphonates into MOF-808 via Ligand Exchange: Stability and Adsorption Properties for Uranium.  ACS Applied Materials & Interfaces,  11  (37): (33931–33940).  [PMID:31409065] [10.1021/acsami.9b10920]
6. Qi Zhao, Jian Li, Yang Xu, Dandan Lv, Kanyasiri Rakariyatham, Dayong Zhou.  (2019)  Rapid extraction of free fatty acids from edible oil after accelerated storage based on amino-modified magnetic silica nanospheres.  Analytical Methods,  11  (35): (4520-4527).  [PMID:] [10.1039/C9AY01082C]
7. Hongkai Xie, Dayong Zhou, Xiaopei Hu, Zhongyuan Liu, Liang Song, Beiwei Zhu.  (2018)  Changes in Lipid Profiles of Dried Clams (Mactra chinensis Philippi and Ruditapes philippinarum) during Accelerated Storage and Prediction of Shelf Life.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,  66  (29): (7764–7774).  [PMID:29965751] [10.1021/acs.jafc.8b03047]
8. Wanpeng Ma, Wei Zhang, Yang Zhao, Helong Yu.  (2016)  Preparation and assessment of a self-healing material based on microcapsules filled with ethyl phenylacetate.  JOURNAL OF APPLIED POLYMER SCIENCE,  133  (20):   [PMID:] [10.1002/app.43430]

References

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2. I Hafström,B Ringertz,H Gyllenhammar,J Palmblad,M Harms-Ringdahl.  (1988-05-01)  Effects of fasting on disease activity, neutrophil function, fatty acid composition, and leukotriene biosynthesis in patients with rheumatoid arthritis..  Arthritis and rheumatism,  31  ((5)): (585-592).  [PMID:2837251]
3. W Herrmann,J Beitz.  (1987-03-01)  [Decreasing atherogenic risks by an eicosapentaenoic acid-rich diet]..  Zeitschrift fur die gesamte innere Medizin und ihre Grenzgebiete,  42  ((5)): (117-122).  [PMID:3035811]
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16. Saleh Abdelhamid,Roland Blomer,Gerhard Hommel,Doris Haack,Sabina Lewicka,Peter Fiegel,Bernd Krumme.  (2003-07-10)  Urinary tetrahydroaldosterone as a screening method for primary aldosteronism: a comparative study..  American journal of hypertension,  16  ((7)): (522-530).  [PMID:12850384]
17. Hyeon Ho Kim,Chung Min Shin,Chi-Hyun Park,Kyu Han Kim,Kwang Hyun Cho,Hee Chul Eun,Jin Ho Chung.  (2005-06-03)  Eicosapentaenoic acid inhibits UV-induced MMP-1 expression in human dermal fibroblasts..  Journal of lipid research,  46  ((8)): (1712-1720).  [PMID:15930517]
18. Vigdis Aas,Merethe H Rokling-Andersen,Eili Tranheim Kase,G Hege Thoresen,Arild C Rustan.  (2005-11-23)  Eicosapentaenoic acid (20:5 n-3) increases fatty acid and glucose uptake in cultured human skeletal muscle cells..  Journal of lipid research,  47  ((2)): (366-374).  [PMID:16301737]
19. Hyeon Ho Kim,Soyun Cho,Serah Lee,Kyu Han Kim,Kwang Hyun Cho,Hee Chul Eun,Jin Ho Chung.  (2006-02-10)  Photoprotective and anti-skin-aging effects of eicosapentaenoic acid in human skin in vivo..  Journal of lipid research,  47  ((5)): (921-930).  [PMID:16467281]
20. Marcy J Balunas,Bin Su,Serena Landini,Robert W Brueggemeier,A Douglas Kinghorn.  (2006-04-29)  Interference by naturally occurring fatty acids in a noncellular enzyme-based aromatase bioassay..  Journal of natural products,  69  ((4)): (700-703).  [PMID:16643058]
21. Keisuke Hino,Yasuko Murakami,Ayako Nagai,Akira Kitase,Yuichi Hara,Takakazu Furutani,Fenyu Ren,Yuhki Yamaguchi,Kohki Yutoku,Satoyoshi Yamashita,Michiari Okuda,Misako Okita,Kiwamu Okita.  (2006-07-29)  Alpha-tocopherol [corrected] and ascorbic acid attenuates the ribavirin [corrected] induced decrease of eicosapentaenoic acid in erythrocyte membrane in chronic hepatitis C patients..  Journal of gastroenterology and hepatology,  21  ((8)): (1269-1275).  [PMID:16872308]
22. Wendy L Hall,Katie A Sanders,Thomas A B Sanders,Philip J Chowienczyk.  (2008-01-22)  A high-fat meal enriched with eicosapentaenoic acid reduces postprandial arterial stiffness measured by digital volume pulse analysis in healthy men..  The Journal of nutrition,  138  ((2)): (287-291).  [PMID:18203893]
23. Pietro Minuz,Houli Jiang,Cristiano Fava,Lucia Turolo,Stefania Tacconelli,Marco Ricci,Paola Patrignani,Alberto Morganti,Alessandro Lechi,John C McGiff.  (2008-04-02)  Altered release of cytochrome p450 metabolites of arachidonic acid in renovascular disease..  Hypertension (Dallas, Tex. : 1979),  51  ((5)): (1379-1385).  [PMID:18378855]
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26. David S Wishart,Craig Knox,An Chi Guo,Roman Eisner,Nelson Young,Bijaya Gautam,David D Hau,Nick Psychogios,Edison Dong,Souhaila Bouatra,Rupasri Mandal,Igor Sinelnikov,Jianguo Xia,Leslie Jia,Joseph A Cruz,Emilia Lim,Constance A Sobsey,Savita Shrivastava,Paul Huang,Philip Liu,Lydia Fang,Jun Peng,Ryan Fradette,Dean Cheng,Dan Tzur,Melisa Clements,Avalyn Lewis,Andrea De Souza,Azaret Zuniga,Margot Dawe,Yeping Xiong,Derrick Clive,Russ Greiner,Alsu Nazyrova,Rustem Shaykhutdinov,Liang Li,Hans J Vogel,Ian Forsythe.  (2008-10-28)  HMDB: a knowledgebase for the human metabolome..  Nucleic acids research,  37  ((Database issue)): (D603-D610).  [PMID:18953024]
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Solution Calculators