3-DEAZANEPLANOCIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C12H14N4O3
Molecular Weight	262.2646
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC=CC2=C1N=CN2[C@@H]3C=C(CO)[C@@H](O)[C@H]3O

InChI

InChIKey=OMKHWTRUYNAGFG-IEBDPFPHSA-N

InChI=1S/C12H14N4O3/c13-12-9-7(1-2-14-12)16(5-15-9)8-3-6(4-17)10(18)11(8)19/h1-3,5,8,10-11,17-19H,4H2,(H2,13,14)/t8-,10-,11+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C12H14N4O3
Molecular Weight	262.2646
Charge	0
Count

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

Approval Year

Targets

Primary Target	Pharmacology	Potency
Histone-lysine N-methyltransferase EZH2 10 Target ID: CHEMBL2189110 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19638619\|https://www.ncbi.nlm.nih.gov/pubmed/26631032	Inhibitor 8297	0.08 µM [IC50]
Adenosylhomocysteinase 5 Target ID: CHEMBL2664 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3790170	Inhibitor 8297	50.0 pM [Ki]
Vaccinia virus 1 Target ID: CHEMBL613493 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26314922	Inhibitor 8297
Yellow fever virus 4 Target ID: CHEMBL613731 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26314922	Inhibitor 8297
Human parainfluenza virus 3 1 Target ID: CHEMBL613126 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26314922	Inhibitor 8297

PubMed

Title	Date	PubMed
Broad-spectrum antiviral activities of neplanocin A, 3-deazaneplanocin A, and their 5'-nor derivatives.	1989 Aug	2552906
Synthesis of 3-deazaneplanocin A, a powerful inhibitor of S-adenosylhomocysteine hydrolase with potent and selective in vitro and in vivo antiviral activities.	1989 Jul	2544721
Inhibitory activity of S-adenosylhomocysteine hydrolase inhibitors against human cytomegalovirus replication.	1993 Jul	8215298
Anti-human immunodeficiency virus 1 (HIV-1) activities of 3-deazaadenosine analogs: increased potency against 3'-azido-3'-deoxythymidine-resistant HIV-1 strains.	1995 Jan 3	7816820
S-adenosylhomocysteine hydrolase inhibitors interfere with the replication of human immunodeficiency virus type 1 through inhibition of the LTR transactivation.	1997 Dec	9396786
Carbocyclic adenosine analogues as S-adenosylhomocysteine hydrolase inhibitors and antiviral agents: recent advances.	1998 Jan-Mar	9708366
Carboxy terminal variants of Epstein-Barr virus-encoded latent membrane protein 1 during long-term human immunodeficiency virus infection: reliable markers for individual strain identification.	1999 Jan	9841847
Treatment of lethal Ebola virus infection in mice with a single dose of an S-adenosyl-L-homocysteine hydrolase inhibitor.	2000 Feb	10809022
Vaccinia virus inhibitors as a paradigm for the chemotherapy of poxvirus infections.	2001 Apr	11292644
3-deazaneplanocin A induces massively increased interferon-alpha production in Ebola virus-infected mice.	2002 Jul	12076759
Identification of active antiviral compounds against a New York isolate of West Nile virus.	2002 Jul	12076755
Potential antiviral therapeutics for smallpox, monkeypox and other orthopoxvirus infections.	2003 Jan	12615299
Anti-HIV-1 activity of 3-deaza-adenosine analogs. Inhibition of S-adenosylhomocysteine hydrolase and nucleotide congeners.	2003 Sep	12919315
Inhibition of severe acute respiratory syndrome-associated coronavirus (SARSCoV) by calpain inhibitors and beta-D-N4-hydroxycytidine.	2004 Jan	15074711
Disruption of the MYC-miRNA-EZH2 loop to suppress aggressive B-cell lymphoma survival and clonogenicity.	2013 Dec	23538750
Epigenetic silencing of microRNA-218 via EZH2-mediated H3K27 trimethylation is involved in malignant transformation of HBE cells induced by cigarette smoke extract.	2016 Feb	25526925

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:39:58 GMT 2023` Edited by `admin` on `Sat Dec 16 08:39:58 GMT 2023`
Record UNII	544SH4020S
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

3-DEAZANEPLANOCIN

Common Name

English

(1S,2R,5R)-5-(4-AMINOIMIDAZO(4,5-C)PYRIDIN-1-YL)-3-(HYDROXYMETHYL)CYCLOPENT-3-ENE-1,2-DIOL

Systematic Name

English

Code System Code Type Description

FDA UNII

544SH4020S