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329-89-5

329-89-5 | 6-Aminonicotinamide

CAS No: 329-89-5 Catalog No: AG003N2V MDL No:MFCD00006327

Product Description

Catalog Number:
AG003N2V
Chemical Name:
6-Aminonicotinamide
CAS Number:
329-89-5
Molecular Formula:
C6H7N3O
Molecular Weight:
137.1393
MDL Number:
MFCD00006327
IUPAC Name:
6-aminopyridine-3-carboxamide
InChI:
InChI=1S/C6H7N3O/c7-5-2-1-4(3-9-5)6(8)10/h1-3H,(H2,7,9)(H2,8,10)
InChI Key:
ZLWYEPMDOUQDBW-UHFFFAOYSA-N
SMILES:
Nc1ccc(cn1)C(=O)N
EC Number:
206-349-7
UNII:
D6FNW67F2B
NSC Number:
21206

Properties

Complexity:
137  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
137.059g/mol
Formal Charge:
0
Heavy Atom Count:
10  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
137.142g/mol
Monoisotopic Mass:
137.059g/mol
Rotatable Bond Count:
1  
Topological Polar Surface Area:
82A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
0.7  

Literature

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2-Deoxy-D-glucose and 6-aminonicotinamide-mediated Nrf2 down regulation leads to radiosensitization of malignant cells via abrogation of GSH-mediated defense. Free radical research 20121201
Radiosensitization by 2-deoxy-D-glucose and 6-aminonicotinamide involves activation of redox sensitive ASK1-JNK/p38MAPK signaling in head and neck cancer cells. Free radical biology & medicine 20121001
A combination of 2-deoxy-D-glucose and 6-aminonicotinamide induces cell cycle arrest and apoptosis selectively in irradiated human malignant cells. Tumour biology : the journal of the International Society for Oncodevelopmental Biology and Medicine 20120801
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JC virus T-antigen regulates glucose metabolic pathways in brain tumor cells. PloS one 20120101
Activation of β-catenin by oncogenic PIK3CA and EGFR promotes resistance to glucose deprivation by inducing a strong antioxidant response. PloS one 20120101
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NADPH oxidase activation by hyperglycaemia in cardiomyocytes is independent of glucose metabolism but requires SGLT1. Cardiovascular research 20111101
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Dehydroepiandrosterone inhibits glucose flux through the pentose phosphate pathway in human and mouse endometrial stromal cells, preventing decidualization and implantation. Molecular endocrinology (Baltimore, Md.) 20110801
Controlled release of 6-aminonicotinamide from aligned, electrospun fibers alters astrocyte metabolism and dorsal root ganglia neurite outgrowth. Journal of neural engineering 20110801
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IGF-1 induction by acylated steryl β-glucosides found in a pre-germinated brown rice diet reduces oxidative stress in streptozotocin-induced diabetes. PloS one 20110101
Teratogen-induced oxidative stress targets glyceraldehyde-3-phosphate dehydrogenase in the organogenesis stage mouse embryo. Toxicological sciences : an official journal of the Society of Toxicology 20101201
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Genes, environment, and orofacial clefting: N-acetyltransferase and folic acid. The Journal of craniofacial surgery 20100901
Delineating biological pathways unique to embryonic stem cell-derived insulin-producing cell lines from their noninsulin-producing progenitor cell lines. Endocrinology 20100801
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Transcriptomics-based identification of developmental toxicants through their interference with cardiomyocyte differentiation of embryonic stem cells. Toxicology and applied pharmacology 20100315
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Glucose regulated protein 78 prompts scavenger receptor A-mediated secretion of tumor necrosis factor-α by RAW 264.7 cells. Clinical and experimental pharmacology & physiology 20090901
Synergistic activation of glucose-6-phosphate dehydrogenase and NAD(P)H oxidase by Src kinase elevates superoxide in type 2 diabetic, Zucker fa/fa, rat liver. Free radical biology & medicine 20090801
Reactive oxygen species-independent oxidation of thioredoxin in hypoxia: inactivation of ribonucleotide reductase and redox-mediated checkpoint control. The Journal of biological chemistry 20090619
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Confirmation of the role of N-acetyltransferase 2 in teratogen-induced cleft palate using transgenics and knockouts. Molecular reproduction and development 20080601
Oxidative pentose phosphate pathway-dependent sugar sensing as a mechanism for regulation of root ion transporters by photosynthesis. Plant physiology 20080401
1-Methylnicotinamide and nicotinamide: two related anti-inflammatory agents that differentially affect the functions of activated macrophages. Archivum immunologiae et therapiae experimentalis 20080401
The role of multiple drug resistance proteins in fetal and/or placental protection against teratogen-induced orofacial clefting. Molecular reproduction and development 20071101
The discovery of 6-amino nicotinamides as potent and selective histone deacetylase inhibitors. Bioorganic & medicinal chemistry letters 20071001
Pro-inflammatory cytokines increase reactive oxygen species through mitochondria and NADPH oxidase in cultured RPE cells. Experimental eye research 20071001
Upregulation of glucose-6-phosphate dehydrogenase and NAD(P)H oxidase activity increases oxidative stress in failing human heart. Journal of cardiac failure 20070801
The effect of glucose on the progression of the nuclear maturation of pig oocytes. Animal reproduction science 20070601
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Thiol oxidation inhibits nitric oxide-mediated pulmonary artery relaxation and guanylate cyclase stimulation. American journal of physiology. Lung cellular and molecular physiology 20060301
Role of pentose phosphate pathway-derived NADPH in hypoxic pulmonary vasoconstriction. Pulmonary pharmacology & therapeutics 20060101
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Effects of D-glucose concentration, D-fructose, and inhibitors of enzymes of the pentose phosphate pathway on the development and sex ratio of bovine blastocysts. Molecular reproduction and development 20051001
Fetal hydrocephalus, intrauterine diagnosis and therapy considerations: an experimental rat model. Child's nervous system : ChNS : official journal of the International Society for Pediatric Neurosurgery 20050501
Radiosensitization by 6-aminonicotinamide and 2-deoxy-D-glucose in human cancer cells. International journal of radiation biology 20050501
Involvement of the pentose phosphate pathway and redox regulation in fertilization in the mouse. Molecular reproduction and development 20050401
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Cytosolic NADPH may regulate differences in basal Nox oxidase-derived superoxide generation in bovine coronary and pulmonary arteries. American journal of physiology. Heart and circulatory physiology 20050101
Metallothionein mediates leukocyte chemotaxis. BMC immunology 20050101
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Radiosensitization of murine Ehrlich ascites tumor by a combination of 2-deoxy-D-glucose and 6-aminonicotinamide. Technology in cancer research & treatment 20041201
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Metallothionein prevents neurodegeneration and central nervous system cell death after treatment with gliotoxin 6-aminonicotinamide. Journal of neuroscience research 20040701
Effects of oxidative stress and inhibitors of the pentose phosphate pathway on sexually dimorphic production of IFN-tau by bovine blastocysts. Molecular reproduction and development 20040501
Inhibition of the pentose phosphate pathway decreases ischemia-reperfusion-induced creatine kinase release in the heart. Cardiovascular research 20040401
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Insulin stimulates glucose metabolism via the pentose phosphate pathway in Drosophila Kc cells. FEBS letters 20031204
Pentose phosphate pathway coordinates multiple redox-controlled relaxing mechanisms in bovine coronary arteries. American journal of physiology. Heart and circulatory physiology 20031201
Contribution of oxidative stress to radiosensitization by a combination of 2-DG and 6-AN in human cancer cell line. Indian journal of experimental biology 20031201
Effects of 6-aminonicotinamide gliotoxin on blood-brain barrier differentiation in the chick embryo cerebellum. Anatomy and embryology 20031001
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Energy metabolism and cerebral blood flow during cytotoxic brain edema induced by 6-aminonicotinamide. Acta neurochirurgica. Supplement 20030101
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Effects of ATP on the stability of enzymes against heat treatment in 6-aminonicotinamide treated quail. The international journal of biochemistry & cell biology 20020901
Frozen-sectioning yields similar results as traditional methods for fetal cephalic examination in the rat. Teratology 20020801
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