PUGNAC

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H19N3O7
Molecular Weight	353.3273
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O\C1=N/OC(=O)NC2=CC=CC=C2

InChI

InChIKey=PBLNJFVQMUMOJY-JXZOILRNSA-N

InChI=1S/C15H19N3O7/c1-8(20)16-11-13(22)12(21)10(7-19)24-14(11)18-25-15(23)17-9-5-3-2-4-6-9/h2-6,10-13,19,21-22H,7H2,1H3,(H,16,20)(H,17,23)/b18-14-/t10-,11-,12-,13-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C15H19N3O7
Molecular Weight	353.3273
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	1
Optical Activity	UNSPECIFIED

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Protein O-GlcNAcase 2 Target ID: O60502\|\|\|Q9HAR0 Gene ID: 10724.0 Gene Symbol: MGEA5 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15795231 \| https://www.ncbi.nlm.nih.gov/pubmed/16214344 \| https://www.ncbi.nlm.nih.gov/pubmed/8034696	Inhibitor 8297		46.0 nM [Ki]
Beta-N-acetyl-D-hexosaminidase-A/B 1 Target ID: CHEMBL3038485 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15795231 \| https://www.ncbi.nlm.nih.gov/pubmed/16214344 \| https://www.ncbi.nlm.nih.gov/pubmed/8034696	Inhibitor 8297		36.0 nM [Ki]

PubMed

Title	Date	PubMed
Purification and characterization of an O-GlcNAc selective N-acetyl-beta-D-glucosaminidase from rat spleen cytosol.	1994 Jul 29	8034696
O-GlcNAcase uses substrate-assisted catalysis: kinetic analysis and development of highly selective mechanism-inspired inhibitors.	2005 Jul 8	15795231
Inhibition of O-GlcNAcase by PUGNAc is dependent upon the oxime stereochemistry.	2006 Feb 1	16214344

Substance Class	Chemical Created by `admin` on `Sat Dec 16 19:06:42 GMT 2023` Edited by `admin` on `Sat Dec 16 19:06:42 GMT 2023`
Record UNII	AWZ7VE64B6
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PUGNAC

Code

English

O-(2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLIDENE)AMINON-PHENYLCARBAMATE

Systematic Name

English

(5R,6R,7S,8R,Z)-6,7-DIHYDROXY-8-(HYDROXYMETHYL)-2,3-DIOXO-N-((PHENYLCARBAMOYL)OXY)-1,4-OXAZOCANE-5-CARBIMIDIC ACID

Systematic Name

English

D-GLUCONIMIDIC ACID, 2-(ACETYLAMINO)-2-DEOXY-N-(((PHENYLAMINO)CARBONYL)OXY)-, .DELTA.-LACTONE, (1Z)-

Systematic Name

English

(Z)-PUGNAC

Common Name

English

Code System Code Type Description

PUBCHEM

9576811