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
Investigations into the origin of the molecular recognition of several adenosine deaminase inhibitors.	2011-01-13	21138280
A quantitative systems approach reveals dynamic control of tRNA modifications during cellular stress.	2010-12-16	21187895
Structural basis for the growth factor activity of human adenosine deaminase ADA2.	2010-04-16	20147294
Structural and metabolic specificity of methylthiocoformycin for malarial adenosine deaminases.	2009-10-13	19728741
Preclinical assessment of the treatment of second-stage African trypanosomiasis with cordycepin and deoxycoformycin.	2009-08-04	19652702
Divergence of AMP Deaminase in the Ice Worm Mesenchytraeus solifugus (Annelida, Clitellata, Enchytraeidae).	2009-07-05	21350654
The 1.25 A resolution structure of phosphoribosyl-ATP pyrophosphohydrolase from Mycobacterium tuberculosis.	2008-06	18560150
Mechanisms of cell death induced by 2-chloroadenosine in leukemic B-cells.	2008-04-01	18242582
AMP-activated protein kinase-independent inhibition of hepatic mitochondrial oxidative phosphorylation by AICA riboside.	2007-06-15	17324122
Synthesis of 5'-methylthio coformycins: specific inhibitors for malarial adenosine deaminase.	2007-05-30	17488013
Adenosine and lymphocyte regulation.	2007-03	18404424
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.	2006-01	16411656
Treatment of African trypanosomiasis with cordycepin and adenosine deaminase inhibitors in a mouse model.	2005-11-01	16206083
Crystallization and preliminary X-ray crystallographic analysis of adenosine 5'-monophosphate deaminase (AMPD) from Arabidopsis thaliana in complex with coformycin 5'-phosphate.	2005-08-01	16511144
Inhibitors of adenosine deaminase: continued studies of structure-activity relationships in analogues of coformycin.	2004	15043152
Dominant localization of adenosine deaminase in leptomeninges and involvement of the enzyme in sleep.	2003-12-05	14630012
Extracellular ATP and adenosine induce cell apoptosis of human hepatoma Li-7A cells via the A3 adenosine receptor.	2003-11	14530217
Adenosine inhibits activation-induced T cell expression of CD2 and CD28 co-stimulatory molecules: role of interleukin-2 and cyclic AMP signaling pathways.	2003-08-01	12874832
Enantiospecific synthesis of carbapentostatins.	2003-01-10	12515468
Ring-expanded ("Fat") nucleosides as broad-spectrum anticancer and antiviral agents.	2002-10	12173969
Adenosine acts through an A3 receptor to prevent the induction of murine anti-CD3-activated killer T cells.	2002-05-20	11992407
Direct measurement of local and global contributions in the binding of coformycin to bovine adenosine deaminase.	2002-04	12420753
Enhancement of cellular adenosine triphosphate levels in PC12 cells by extracellular adenosine.	2002-03	11913523
2-Chloroadenosine but not adenosine induces apoptosis in rheumatoid fibroblasts independently of cell surface adenosine receptor signalling.	2002-03	11906961
Binding thermodynamics of the transition state analogue coformycin and of the ground state analogue 1-deazaadenosine to bovine adenosine deaminase.	2001	11697042
Antifungal activity of 3'-deoxyadenosine (cordycepin).	1998-06	9624488
Reversion in Chinese hamster lines amplified at the AMPD2 locus: spontaneous and benzamide-stimulated gradual loss of amplified alleles of marker genes.	1996-01-17	8569793

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:07:48 GMT 2025` Edited by `admin` on `Mon Mar 31 19:07:48 GMT 2025`
Record UNII	E49510ZL0H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

COFORMYCIN

Common Name

English

NSC-277817

Preferred Name

English

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

Systematic Name

English

Code System Code Type Description

CAS

11033-22-0