N6-METHYLDEOXYADENOSINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C11H15N5O3
Molecular Weight	265.2685
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CNC1=NC=NC2=C1N=CN2[C@H]3C[C@H](O)[C@@H](CO)O3

InChI

InChIKey=DYSDOYRQWBDGQQ-XLPZGREQSA-N

InChI=1S/C11H15N5O3/c1-12-10-9-11(14-4-13-10)16(5-15-9)8-2-6(18)7(3-17)19-8/h4-8,17-18H,2-3H2,1H3,(H,12,13,14)/t6-,7+,8+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C11H15N5O3
Molecular Weight	265.2685
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Inhibition of platelet function by administration of MRS2179, a P2Y1 receptor antagonist.	2001 Feb 2	11166284
Key role of the P2Y(1) receptor in tissue factor-induced thrombin-dependent acute thromboembolism: studies in P2Y(1)-knockout mice and mice treated with a P2Y(1) antagonist.	2001 Feb 6	11156884
The bacterial nucleoside N(6)-methyldeoxyadenosine induces the differentiation of mammalian tumor cells.	2001 Jul 20	11453663
Extracellular ADP is a powerful osteolytic agent: evidence for signaling through the P2Y(1) receptor on bone cells.	2001 May	11344082
Novel antagonists acting at the P2Y(1) purinergic receptor: synthesis and conformational analysis using potentiometric and nuclear magnetic resonance titration techniques.	2002 Feb 14	11831909
Nucleotide-mediated relaxation in guinea-pig aorta: selective inhibition by MRS2179.	2002 Jan	11815389
Effects of dinucleoside polyphosphates on regulation of coronary vascular tone.	2002 Jul 19	12144943
Effects of inhibition of P2Y(1) and P2Y(12) on whole blood clotting, coagulum elasticity and fibrinolysis resistance studied with free oscillation rheometry.	2003 Mar 15	12818256
Induction of neurite outgrowth in PC12 cells by the bacterial nucleoside N6-methyldeoxyadenosine is mediated through adenosine A2a receptors and via cAMP and MAPK signaling pathways.	2003 May 16	12727227
Nucleotide-mediated calcium signaling in rat cortical astrocytes: Role of P2X and P2Y receptors.	2003 Sep	12898701
Synergistic action between inhibition of P2Y12/P2Y1 and P2Y12/thrombin in ADP- and thrombin-induced human platelet activation.	2004 Aug	15265806
Direct excitation of inhibitory interneurons by extracellular ATP mediated by P2Y1 receptors in the hippocampal slice.	2004 Dec 1	15574734
ATP release triggered by activation of the Ca2+-activated K+ channel in human airway Calu-3 cells.	2004 Mar	12947021
Stimulation of Xenopus P2Y1 receptor activates CFTR in A6 cells.	2004 Oct	15235914
Regulation of rat hepatocyte function by P2Y receptors: focus on control of glycogen phosphorylase and cyclic AMP by 2-methylthioadenosine 5'-diphosphate.	2004 Oct	15152027
Metabotropic P2Y purinoceptor-mediated presynaptic and postsynaptic enhancement of cerebellar GABAergic transmission.	2005 Feb 23	15728851
ADP acting on P2Y13 receptors is a negative feedback pathway for ATP release from human red blood cells.	2005 Feb 4	15604418
Inhibition of purinoceptors amplifies glucose-stimulated insulin release with removal of its pulsatility.	2005 Jul	15983214
Neurogenic secretion mediated by the purinergic P2Y1 receptor in guinea-pig small intestine.	2006 Apr 24	16566916
Extracellular nucleotide signaling in adult neural stem cells: synergism with growth factor-mediated cellular proliferation.	2006 Feb	16436623
Glucose induces glucagon release pulses antisynchronous with insulin and sensitive to purinoceptor inhibition.	2006 Jul	16614082
Can the PFA-100 be modified to detect P2Y12 inhibition?	2006 Jun	16706997
Activation of P2Y1 receptor triggers two calcium signaling pathways in bone marrow erythroblasts.	2006 Mar 18	16487961
Undetectable levels of N6-methyl adenine in mouse DNA: Cloning and analysis of PRED28, a gene coding for a putative mammalian DNA adenine methyltransferase.	2006 May 29	16684535
Enhanced food intake after stimulation of hypothalamic P2Y1 receptors in rats: modulation of feeding behaviour by extracellular nucleotides.	2006 Oct	17067301
Pulses of somatostatin release are slightly delayed compared with insulin and antisynchronous to glucagon.	2007 Dec 4	17628719
A novel mechanism of vasoregulation: ADP-induced relaxation of the porcine isolated coronary artery is mediated via adenosine release.	2007 Feb	17167068
Evidence that ATP or a related purine is an excitatory neurotransmitter in the longitudinal muscle of mouse distal colon.	2007 May	17351663
P2Y receptor-activating nucleotides modulate cellular reactive oxygen species production in dissociated hippocampal astrocytes and neurons in culture independent of parallel cytosolic Ca(2+) rise and change in mitochondrial potential.	2007 Nov 15	17492786
Effects of P2Y1 receptor on glial fibrillary acidic protein and glial cell line-derived neurotrophic factor production of astrocytes under ischemic condition and the related signaling pathways.	2008 Aug	18668152
Ca2+ signaling in injured in situ endothelium of rat aorta.	2008 Sep	18276005
Role of P2Y1 receptor in astroglia-to-neuron signaling at dorsal spinal cord.	2009 Sep	19396875
CNGA2 contributes to ATP-induced noncapacitative Ca2+ influx in vascular endothelial cells.	2010	19729961
Two-pore potassium ion channels are inhibited by both G(q/11)- and G(i)-coupled P2Y receptors.	2010 Apr	20097289
Endogenous purinergic signaling is required for osmotic volume regulation of retinal glial cells.	2010 Mar	20002522

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:15:34 GMT 2023` Edited by `admin` on `Fri Dec 15 17:15:34 GMT 2023`
Record UNII	48QZW2IR9H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

N6-METHYLDEOXYADENOSINE

Systematic Name

English

NSC-66392

Code

English

ADENOSINE, 2'-DEOXY-N-METHYL-

Systematic Name

English

2'-DEOXY-N6-METHYLADENOSINE

Systematic Name

English

6-(METHYLAMINO)PURINE DEOXYRIBOSIDE

Common Name

English

N6-METHYL-2'-DEOXYADENOSINE

Systematic Name

English

Code System Code Type Description

NSC

66392