N-Acetyl-b-D-galactosamine (BioDeep_00000014381)
Secondary id: BioDeep_00001868871
human metabolite Endogenous
代谢物信息卡片
N-[(2R,3R,4R,5R,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
化学式: C8H15NO6 (221.089933)
中文名称:
谱图信息:
最多检出来源 Homo sapiens(feces) 1.68%
分子结构信息
SMILES: CC(=O)NC1C(C(C(OC1O)CO)O)O
InChI: InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6+,7-,8-/m1/s1
描述信息
N-acetyl-β-d-galactosamine, also known as 2-acetamido-2-deoxy-beta-D-galactopyranoside or 2-deoxy-2-acetamido-B-D-galactopyranose, is a member of the class of compounds known as N-acyl-alpha-hexosamines. N-acyl-alpha-hexosamines are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group. N-acetyl-β-d-galactosamine is soluble (in water) and a very weakly acidic compound (based on its pKa). N-acetyl-β-d-galactosamine can be found in a number of food items such as opium poppy, watercress, lemon verbena, and green bean, which makes N-acetyl-β-d-galactosamine a potential biomarker for the consumption of these food products.
N-Acetyl-b-D-galactosamine is an oligosaccharide residue found in the lining and glandular epithelium, the stroma and the vessels (capillary and large vessels of the human postmenopausal endometrium. (PMID: 8930627). It is suspected that N-Acetyl-b-D-galactosamine is a molecule that binds to IgA in the glomerular mesangium in Henoch-Schoenlein purpura associated nephropathy (the most common vasculitis of childhood). (PMID: 10732728).
同义名列表
30 个代谢物同义名
N-[(2R,3R,4R,5R,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide; 2-Deoxy-2-acetamido-beta-delta-galactopyranose; beta-delta-2-Acetamido-2-deoxy-galactopyranose; 2-Acetamido-2-deoxy-beta-D-galactopyranoside; beta-D-2-Acetamido-2-deoxy-galactopyranose; 2-Deoxy-2-acetamido-beta-D-galactopyranose; 2-Acetamido-2-deoxy-β-D-galactopyranoside; 2-Acetamido-2-deoxy-b-D-galactopyranoside; 2-Deoxy-2-acetamido-b-D-galactopyranose; b-D-2-Acetamido-2-deoxy-galactopyranose; beta-N-Acetyl-delta-galactosamine; 2-Acetamido-2-deoxy-D-galactose; 2 Acetamido 2 deoxy D galactose; 2 Acetamido 2 D galactopyranose; 2-Acetamido-2-D-galactopyranose; beta-N-Acetyl-D-galactosamine; 2 Acetamido 2 deoxygalactose; 2-Acetamido-2-deoxygalactose; beta-N-Acetylgalactosamine; N-Acetyl-β-D-galactosamine; N-Acetyl-b-D-galactosamine; b-N-Acetyl-D-galactosamine; N Acetyl D galactosamine; N-Acetyl-D-galactosamine; b-N-Acetylgalactosamine; Acetylgalactosamine; beta-GalNAc; b-GalNAc; Β-galnac; BGalNAc
数据库引用编号
15 个数据库交叉引用编号
- ChEBI: CHEBI:28497
- KEGG: C05021
- PubChem: 440552
- HMDB: HMDB0000853
- ChEMBL: CHEMBL39064
- MeSH: Acetylgalactosamine
- MetaCyc: CPD-12557
- foodb: FDB031024
- chemspider: 389452
- CAS: 147995-09-3
- CAS: 130851-15-9
- CAS: 14131-60-3
- PubChem: 7497
- PDB-CCD: NGA
- NIKKAJI: J1.797.265K
分类词条
相关代谢途径
BioCyc(0)
PlantCyc(0)
代谢反应
10 个相关的代谢反应过程信息。
Reactome(4)
- Metabolism:
3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-one-CoA + CoA-SH ⟶ choloyl-CoA + propionyl CoA - Amino acid and derivative metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Selenoamino acid metabolism:
H2O + SeMet ⟶ 2OBUTA + MeSeH + ammonia - Formation of selenosugars for excretion:
MeSebGalNac ⟶ 2-acetamidoglucal + MeSeO2H
BioCyc(6)
- dermatan sulfate degradation (metazoa):
dermatan sulfate ⟶ α-L-iduronate + N-acetyl-β-D-galactosamine + sulfate - dermatan sulfate degradation (metazoa):
dermatan sulfate ⟶ α-L-idopyranuronate + N-acetyl-β-D-galactosamine + sulfate - chondroitin sulfate degradation (metazoa):
chondroitin sulfate ⟶ N-acetyl-β-D-galactosamine + D-glucopyranuronate - chondroitin sulfate degradation (metazoa):
chondroitin sulfate ⟶ N-acetyl-β-D-galactosamine + D-glucopyranuronate + sulfate - chondroitin sulfate and dermatan sulfate degradation I (bacterial):
4-deoxy-β-D-gluc-4-enuronosyl-(1,3)-N-acetyl-D-galactosamine 4-sulfate + H2O ⟶ 4-deoxy-β-D-gluc-4-enuronosyl-(1,3)-N-acetyl-D-galactosamine + H+ + sulfate - chondroitin sulfate and dermatan sulfate degradation I (bacterial):
4-deoxy-β-D-gluc-4-enuronosyl-(1,3)-N-acetyl-D-galactosamine 4-sulfate + H2O ⟶ β-D-4-deoxy-gluc-4-enuronosyl-(1,3)-N-acetyl-D-galactosamine + H+ + sulfate
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
1 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
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10.1002/jlcr.3697. [PMID: 30548247] - Stanley T Crooke, Brenda F Baker, Shuting Xia, Rosie Z Yu, Nicholas J Viney, Yanfeng Wang, Sotirios Tsimikas, Richard S Geary. Integrated Assessment of the Clinical Performance of GalNAc3-Conjugated 2'-O-Methoxyethyl Chimeric Antisense Oligonucleotides: I. Human Volunteer Experience.
Nucleic acid therapeutics.
2019 02; 29(1):16-32. doi:
10.1089/nat.2018.0753. [PMID: 30570431] - Mamta Sharma, Prajna Hegde, Kavita Hiremath, Vishwanath Reddy H, A S Kamalanathan, Bale M Swamy, Shashikala R Inamdar. Purification, characterization and fine sugar specificity of a N-Acetylgalactosamine specific lectin from Adenia hondala.
Glycoconjugate journal.
2018 12; 35(6):511-523. doi:
10.1007/s10719-018-9843-6. [PMID: 30306293] - Timothy A Su, Diyala S Shihadih, Wendy Cao, Tyler C Detomasi, Marie C Heffern, Shang Jia, Andreas Stahl, Christopher J Chang. A Modular Ionophore Platform for Liver-Directed Copper Supplementation in Cells and Animals.
Journal of the American Chemical Society.
2018 10; 140(42):13764-13774. doi:
10.1021/jacs.8b08014. [PMID: 30351140] - Maja M Janas, Carole E Harbison, Victoria K Perry, Brenda Carito, Jessica E Sutherland, Akshay K Vaishnaw, Natalie D Keirstead, Garvin Warner. The Nonclinical Safety Profile of GalNAc-conjugated RNAi Therapeutics in Subacute Studies.
Toxicologic pathology.
2018 10; 46(7):735-745. doi:
10.1177/0192623318792537. [PMID: 30139307] - Xin You, Hongqiang Qin, Jiawei Mao, Yu Tian, Mingming Dong, Zhimou Guo, Xinmiao Liang, Liming Wang, Yan Jin, Mingliang Ye. Highly Efficient Identification of O-GalNAc Glycosylation by an Acid-Assisted Glycoform Simplification Approach.
Proteomics.
2018 09; 18(17):e1800042. doi:
10.1002/pmic.201800042. [PMID: 30033600] - Paul J Schmidt, Kaifeng Liu, Gary Visner, Kevin Fitzgerald, Shannon Fishman, Tim Racie, Julia L Hettinger, James S Butler, Mark D Fleming. RNAi-mediated reduction of hepatic Tmprss6 diminishes anemia and secondary iron overload in a splenectomized mouse model of β-thalassemia intermedia.
American journal of hematology.
2018 Jun; 93(6):745-750. doi:
10.1002/ajh.25079. [PMID: 29498084] - Leif Wide, Karin Eriksson. Low-glycosylated forms of both FSH and LH play major roles in the natural ovarian stimulation.
Upsala journal of medical sciences.
2018 Jun; 123(2):100-108. doi:
10.1080/03009734.2018.1467983. [PMID: 29894213] - Aaron D Springer, Steven F Dowdy. GalNAc-siRNA Conjugates: Leading the Way for Delivery of RNAi Therapeutics.
Nucleic acid therapeutics.
2018 06; 28(3):109-118. doi:
10.1089/nat.2018.0736. [PMID: 29792572] - Shengjun Wang, Yang Mao, Yoshiki Narimatsu, Zilu Ye, Weihua Tian, Christoffer K Goth, Erandi Lira-Navarrete, Nis B Pedersen, Asier Benito-Vicente, Cesar Martin, Kepa B Uribe, Ramon Hurtado-Guerrero, Christina Christoffersen, Nabil G Seidah, Rikke Nielsen, Erik I Christensen, Lars Hansen, Eric P Bennett, Sergey Y Vakhrushev, Katrine T Schjoldager, Henrik Clausen. Site-specific O-glycosylation of members of the low-density lipoprotein receptor superfamily enhances ligand interactions.
The Journal of biological chemistry.
2018 05; 293(19):7408-7422. doi:
10.1074/jbc.m117.817981. [PMID: 29559555] - Fumito Wada, Tsuyoshi Yamamoto, Tetsuya Ueda, Motoki Sawamura, Shunsuke Wada, Mariko Harada-Shiba, Satoshi Obika. Cholesterol-GalNAc Dual Conjugation Strategy for Reducing Renal Distribution of Antisense Oligonucleotides.
Nucleic acid therapeutics.
2018 02; 28(1):50-57. doi:
10.1089/nat.2017.0698. [PMID: 29360004] - Waraporn Saentaweesuk, Atit Silsirivanit, Kulthida Vaeteewoottacharn, Kanlayanee Sawanyawisuth, Chawalit Pairojkul, Ubon Cha'on, Somsiri Indramanee, Somchai Pinlaor, Thidarut Boonmars, Norie Araki, Chaisiri Wongkham. Clinical significance of GalNAcylated glycans in cholangiocarcinoma: Values for diagnosis and prognosis.
Clinica chimica acta; international journal of clinical chemistry.
2018 Feb; 477(?):66-71. doi:
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Journal of clinical lipidology.
2018 Jan; 12(1):122-129.e2. doi:
10.1016/j.jacl.2017.10.024. [PMID: 29174389] - Jarkko J Lackman, Christoffer K Goth, Adnan Halim, Sergey Y Vakhrushev, Henrik Clausen, Ulla E Petäjä-Repo. Site-specific O-glycosylation of N-terminal serine residues by polypeptide GalNAc-transferase 2 modulates human δ-opioid receptor turnover at the plasma membrane.
Cellular signalling.
2018 Jan; 42(?):184-193. doi:
10.1016/j.cellsig.2017.10.016. [PMID: 29097258] - Zhe Tan, Yogesh K Dhande, Theresa M Reineke. Cell Penetrating Polymers Containing Guanidinium Trigger Apoptosis in Human Hepatocellular Carcinoma Cells unless Conjugated to a Targeting N-Acetyl-Galactosamine Block.
Bioconjugate chemistry.
2017 Dec; 28(12):2985-2997. doi:
10.1021/acs.bioconjchem.7b00598. [PMID: 29193962] - Michael Tanowitz, Lisa Hettrick, Alexey Revenko, Garth A Kinberger, Thazha P Prakash, Punit P Seth. Asialoglycoprotein receptor 1 mediates productive uptake of N-acetylgalactosamine-conjugated and unconjugated phosphorothioate antisense oligonucleotides into liver hepatocytes.
Nucleic acids research.
2017 Dec; 45(21):12388-12400. doi:
10.1093/nar/gkx960. [PMID: 29069408] - Yusuke Sato, Hideki Matsui, Naoki Yamamoto, Risa Sato, Tsubasa Munakata, Michinori Kohara, Hideyoshi Harashima. Highly specific delivery of siRNA to hepatocytes circumvents endothelial cell-mediated lipid nanoparticle-associated toxicity leading to the safe and efficacious decrease in the hepatitis B virus.
Journal of controlled release : official journal of the Controlled Release Society.
2017 Nov; 266(?):216-225. doi:
10.1016/j.jconrel.2017.09.044. [PMID: 28986168] - Jayaprakash K Nair, Husain Attarwala, Alfica Sehgal, Qianfan Wang, Krishna Aluri, Xuemei Zhang, Minggeng Gao, Ju Liu, Ramesh Indrakanti, Sally Schofield, Philip Kretschmer, Christopher R Brown, Swati Gupta, Jennifer L S Willoughby, Julie A Boshar, Vasant Jadhav, Klaus Charisse, Tracy Zimmermann, Kevin Fitzgerald, Muthiah Manoharan, Kallanthottathil G Rajeev, Akin Akinc, Renta Hutabarat, Martin A Maier. Impact of enhanced metabolic stability on pharmacokinetics and pharmacodynamics of GalNAc-siRNA conjugates.
Nucleic acids research.
2017 Nov; 45(19):10969-10977. doi:
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European journal of pharmacology.
2017 Oct; 813(?):42-49. doi:
10.1016/j.ejphar.2017.07.022. [PMID: 28709621] - Kazuki Hashiba, Yusuke Sato, Hideyoshi Harashima. pH-labile PEGylation of siRNA-loaded lipid nanoparticle improves active targeting and gene silencing activity in hepatocytes.
Journal of controlled release : official journal of the Controlled Release Society.
2017 Sep; 262(?):239-246. doi:
10.1016/j.jconrel.2017.07.046. [PMID: 28774839] - Ebtesam A Gashash, Arya Aloor, Dong Li, He Zhu, Xiao-Qian Xu, Cong Xiao, Junping Zhang, Aishwarya Parameswaran, Jing Song, Cheng Ma, Weidong Xiao, Peng George Wang. An Insight into Glyco-Microheterogeneity of Plasma von Willebrand Factor by Mass Spectrometry.
Journal of proteome research.
2017 09; 16(9):3348-3362. doi:
10.1021/acs.jproteome.7b00359. [PMID: 28696719] - Ruslan Gibadullin, David Wayne Farnsworth, Joseph J Barchi, Jeffrey C Gildersleeve. GalNAc-Tyrosine Is a Ligand of Plant Lectins, Antibodies, and Human and Murine Macrophage Galactose-Type Lectins.
ACS chemical biology.
2017 08; 12(8):2172-2182. doi:
10.1021/acschembio.7b00471. [PMID: 28644609] - Jacek Lubkowski, Sarah V Durbin, Mariana C C Silva, David Farnsworth, Jeffrey C Gildersleeve, Maria Luiza V Oliva, Alexander Wlodawer. Structural analysis and unique molecular recognition properties of a Bauhinia forficata lectin that inhibits cancer cell growth.
The FEBS journal.
2017 02; 284(3):429-450. doi:
10.1111/febs.13989. [PMID: 27973758] - Jonas Nilsson, Fredrik Noborn, Alejandro Gomez Toledo, Waqas Nasir, Carina Sihlbom, Göran Larson. Characterization of Glycan Structures of Chondroitin Sulfate-Glycopeptides Facilitated by Sodium Ion-Pairing and Positive Mode LC-MS/MS.
Journal of the American Society for Mass Spectrometry.
2017 02; 28(2):229-241. doi:
10.1007/s13361-016-1539-1. [PMID: 27873218] - Rodrigo Rodrigues E Lacerda, Edilza Silva do Nascimento, José Thalles Jocelino Gomes de Lacerda, Luciano da Silva Pinto, Caroline Rizzi, Mirna Marques Bezerra, Isabela Ribeiro Pinto, Samuel Mateus Pereira Filho, Vicente de Paulo Texeira Pinto, Gerardo Cristino Filho, Carlos Alberto de Almeida Gadelha, Tatiane Santi Gadelha. Lectin from seeds of a Brazilian lima bean variety (Phaseolus lunatus L. var. cascavel) presents antioxidant, antitumour and gastroprotective activities.
International journal of biological macromolecules.
2017 Feb; 95(?):1072-1081. doi:
10.1016/j.ijbiomac.2016.10.097. [PMID: 27984144] - Kevin Fitzgerald, Suellen White, Anna Borodovsky, Brian R Bettencourt, Andrew Strahs, Valerie Clausen, Peter Wijngaard, Jay D Horton, Jorg Taubel, Ashley Brooks, Chamikara Fernando, Robert S Kauffman, David Kallend, Akshay Vaishnaw, Amy Simon. A Highly Durable RNAi Therapeutic Inhibitor of PCSK9.
The New England journal of medicine.
2017 01; 376(1):41-51. doi:
10.1056/nejmoa1609243. [PMID: 27959715] - John R Haserick, Joshua A Klein, Catherine E Costello, John Samuelson. Cryptosporidium parvum vaccine candidates are incompletely modified with O-linked-N-acetylgalactosamine or contain N-terminal N-myristate and S-palmitate.
PloS one.
2017; 12(8):e0182395. doi:
10.1371/journal.pone.0182395. [PMID: 28792526] - Rosie Z Yu, Rudy Gunawan, Noah Post, Thomas Zanardi, Shannon Hall, Jennifer Burkey, Tae-Won Kim, Mark J Graham, Thazha P Prakash, Punit P Seth, Eric E Swayze, Richard S Geary, Scott P Henry, Yanfeng Wang. Disposition and Pharmacokinetics of a GalNAc3-Conjugated Antisense Oligonucleotide Targeting Human Lipoprotein (a) in Monkeys.
Nucleic acid therapeutics.
2016 12; 26(6):372-380. doi:
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International journal of biological macromolecules.
2016 Oct; 91(?):75-84. doi:
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Carbohydrate polymers.
2016 08; 147(?):1-7. doi:
10.1016/j.carbpol.2016.03.013. [PMID: 27178902] - Lei Li, Robert L Woodward, Weiqing Han, Jingyao Qu, Jing Song, Cheng Ma, Peng G Wang. Chemoenzymatic synthesis of the bacterial polysaccharide repeating unit undecaprenyl pyrophosphate and its analogs.
Nature protocols.
2016 07; 11(7):1280-98. doi:
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The Journal of pharmacology and experimental therapeutics.
2016 May; 357(2):320-30. doi:
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Circulation research.
2016 Apr; 118(7):1106-15. doi:
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Biomacromolecules.
2016 Mar; 17(3):830-40. doi:
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The international journal of biochemistry & cell biology.
2016 Mar; 72(?):27-39. doi:
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PloS one.
2016; 11(12):e0167611. doi:
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PloS one.
2016; 11(3):e0150561. doi:
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Organic & biomolecular chemistry.
2015 Dec; 13(47):11529-38. doi:
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International wound journal.
2015 Dec; 12(6):674-85. doi:
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Kidney international.
2015 Nov; 88(5):974-89. doi:
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Organic & biomolecular chemistry.
2015 Apr; 13(14):4190-203. doi:
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American journal of physiology. Gastrointestinal and liver physiology.
2015 Mar; 308(6):G510-24. doi:
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The international journal of biochemistry & cell biology.
2015 Feb; 59(?):103-10. doi:
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Molecular phylogenetics and evolution.
2015 Feb; 83(?):184-90. doi:
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Iranian biomedical journal.
2015; 19(1):63-8. doi:
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Analytical sciences : the international journal of the Japan Society for Analytical Chemistry.
2015; 31(12):1255-60. doi:
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Biochimie.
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Anatomia, histologia, embryologia.
2014 Oct; 43(5):352-60. doi:
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PloS one.
2014; 9(2):e89630. doi:
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Nephrology (Carlton, Vic.).
2014 Jan; 19(1):32-9. doi:
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PloS one.
2014; 9(2):e88422. doi:
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Methods in molecular biology (Clifton, N.J.).
2014; 1200(?):165-71. doi:
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Reproduction, fertility, and development.
2014 Jan; 26(2):268-81. doi:
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Molecular and cellular biochemistry.
2013 Nov; 383(1-2):149-59. doi:
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Advanced healthcare materials.
2013 Oct; 2(10):1337-50. doi:
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APMIS : acta pathologica, microbiologica, et immunologica Scandinavica.
2013 Sep; 121(9):890-7. doi:
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Journal of molecular modeling.
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