COFORMYCIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C11H16N4O5
Molecular Weight	284.2685
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2C=NC3=C2N=CNC[C@H]3O

InChI

InChIKey=YOOVTUPUBVHMPG-LODYRLCVSA-N

InChI=1S/C11H16N4O5/c16-2-6-8(18)9(19)11(20-6)15-4-14-7-5(17)1-12-3-13-10(7)15/h3-6,8-9,11,16-19H,1-2H2,(H,12,13)/t5-,6-,8-,9-,11-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C11H16N4O5
Molecular Weight	284.2685
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Reversion in Chinese hamster lines amplified at the AMPD2 locus: spontaneous and benzamide-stimulated gradual loss of amplified alleles of marker genes.	1996 Jan 17	8569793
Antifungal activity of 3'-deoxyadenosine (cordycepin).	1998 Jun	9624488
Binding thermodynamics of the transition state analogue coformycin and of the ground state analogue 1-deazaadenosine to bovine adenosine deaminase.	2001	11697042
Direct measurement of local and global contributions in the binding of coformycin to bovine adenosine deaminase.	2002 Apr	12420753
Enhancement of cellular adenosine triphosphate levels in PC12 cells by extracellular adenosine.	2002 Mar	11913523
2-Chloroadenosine but not adenosine induces apoptosis in rheumatoid fibroblasts independently of cell surface adenosine receptor signalling.	2002 Mar	11906961
Adenosine acts through an A3 receptor to prevent the induction of murine anti-CD3-activated killer T cells.	2002 May 20	11992407
Ring-expanded ("Fat") nucleosides as broad-spectrum anticancer and antiviral agents.	2002 Oct	12173969
Adenosine inhibits activation-induced T cell expression of CD2 and CD28 co-stimulatory molecules: role of interleukin-2 and cyclic AMP signaling pathways.	2003 Aug 1	12874832
Dominant localization of adenosine deaminase in leptomeninges and involvement of the enzyme in sleep.	2003 Dec 5	14630012
Enantiospecific synthesis of carbapentostatins.	2003 Jan 10	12515468
Extracellular ATP and adenosine induce cell apoptosis of human hepatoma Li-7A cells via the A3 adenosine receptor.	2003 Nov	14530217
Inhibitors of adenosine deaminase: continued studies of structure-activity relationships in analogues of coformycin.	2004	15043152
Crystallization and preliminary X-ray crystallographic analysis of adenosine 5'-monophosphate deaminase (AMPD) from Arabidopsis thaliana in complex with coformycin 5'-phosphate.	2005 Aug 1	16511144
Treatment of African trypanosomiasis with cordycepin and adenosine deaminase inhibitors in a mouse model.	2005 Nov 1	16206083
Relatively small increases in the steady-state levels of nucleobase deamination products in DNA from human TK6 cells exposed to toxic levels of nitric oxide.	2006 Jan	16411656
AMP-activated protein kinase-independent inhibition of hepatic mitochondrial oxidative phosphorylation by AICA riboside.	2007 Jun 15	17324122
Adenosine and lymphocyte regulation.	2007 Mar	18404424
Synthesis of 5'-methylthio coformycins: specific inhibitors for malarial adenosine deaminase.	2007 May 30	17488013
Mechanisms of cell death induced by 2-chloroadenosine in leukemic B-cells.	2008 Apr 1	18242582
The 1.25 A resolution structure of phosphoribosyl-ATP pyrophosphohydrolase from Mycobacterium tuberculosis.	2008 Jun	18560150
Preclinical assessment of the treatment of second-stage African trypanosomiasis with cordycepin and deoxycoformycin.	2009 Aug 4	19652702
Divergence of AMP Deaminase in the Ice Worm Mesenchytraeus solifugus (Annelida, Clitellata, Enchytraeidae).	2009 Jul 5	21350654
Structural and metabolic specificity of methylthiocoformycin for malarial adenosine deaminases.	2009 Oct 13	19728741
Structural basis for the growth factor activity of human adenosine deaminase ADA2.	2010 Apr 16	20147294
A quantitative systems approach reveals dynamic control of tRNA modifications during cellular stress.	2010 Dec 16	21187895
Investigations into the origin of the molecular recognition of several adenosine deaminase inhibitors.	2011 Jan 13	21138280

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:11:54 GMT 2023` Edited by `admin` on `Fri Dec 15 18:11:54 GMT 2023`
Record UNII	E49510ZL0H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

COFORMYCIN

Common Name

English

IMIDAZO(4,5-D)(1,3)DIAZEPIN-8-OL, 3,4,7,8-TETRAHYDRO-3-.BETA.-D-RIBOFURANOSYL-, (8R)-

Systematic Name

English

NSC-277817

Code

English

Code System Code Type Description

CAS

11033-22-0