HYDROXYGUANIDINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	CH5N3O
Molecular Weight	75.0699
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=N)NO

InChI

InChIKey=WFBHRSAKANVBKH-UHFFFAOYSA-N

InChI=1S/CH5N3O/c2-1(3)4-5/h5H,(H4,2,3,4)

HIDE SMILES / InChI

Molecular Formula	CH5N3O
Molecular Weight	75.0699
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Dimerization of protegrin-1 in different environments.	2010-09-09	20957087
Reaction of N-hydroxyguanidine with the ferrous-oxy state of a heme peroxidase cavity mutant: a model for the reactions of nitric oxide synthase.	2010-08-01	20346907
Discovery and clinical evaluation of 1-{N-[2-(amidinoaminooxy)ethyl]amino}carbonylmethyl-6-methyl-3-[2,2-difluoro-2-phenylethylamino]pyrazinone (RWJ-671818), a thrombin inhibitor with an oxyguanidine P1 motif.	2010-02-25	20102150
The peptidylglycine alpha-amidating monooxygenase (PAM): a novel prodrug strategy for amidoximes and N-hydroxyguanidines?	2009-10	19693765
N-Hydroxyguanidines oxidation by a N3S copper-complex mimicking the reactivity of Dopamine beta-Hydroxylase.	2009-03	19178946
Synthesis of (+)- and (-)-monanchorin.	2009-02-19	19166346
Identification of non-peptidic neuromedin U receptor modulators by a robust homogeneous screening assay.	2008-04	18358099
2-(2-Chloro-6-fluorophenyl)acetamides as potent thrombin inhibitors.	2007-11-15	17889527
Reactivity of the heme-dioxygen complex of the inducible nitric oxide synthase in the presence of alternative substrates.	2006-01	16367758
Total synthesis of (+)-batzelladine A and (-)-batzelladine D, and identification of their target protein.	2005-11-18	16161173
Metabolism of N-hydroxyguanidines (N-hydroxydebrisoquine) in human and porcine hepatocytes: reduction and formation of glucuronides.	2005-10	16033947
Nomega-hydroxy-L-arginine homologues and hydroxylamine as nitric oxide-dependent vasorelaxant agents.	2005-06-15	15964563
Relationship between the structure of guanidines and N-hydroxyguanidines, their binding to inducible nitric oxide synthase (iNOS) and their iNOS-catalysed oxidation to NO.	2005-06	15955074
Arginase: structure, mechanism, and physiological role in male and female sexual arousal.	2005-03	15766238
N-hydroxyguanidines as substrates of nitric oxide synthases.	2005	16101431
Alternative nitric oxide-producing substrates for NO synthases.	2004-10-15	15451052
Design, synthesis, and biochemical evaluation of novel alpha V beta 3 integrin ligands.	2004-09-06	15357991
[Design, synthesis and antiasthmatic activities of NO-donating seratrodast derivatives].	2004-09	15606018
Synthesis and quantitative structure-activity relationship of hydrazones of N-amino-N'-hydroxyguanidine as electron acceptors for xanthine oxidase.	2004-06-03	15163191
Aromatic N-hydroxyguanidines as new reduction cosubstrates for dopamine beta-hydroxylase.	2004-04-16	15044095
Relaxant effect of oxime derivatives in isolated rat aorta: role of nitric oxide (NO) formation in smooth muscle.	2004-03-15	15006555
The mechanism of L-canavanine cytotoxicity: arginyl tRNA synthetase as a novel target for anticancer drug discovery.	2003-10	14692504
Oxidation of N-hydroxyguanidines by copper(II): model systems for elucidating the physiological chemistry of the nitric oxide biosynthetic intermediate N-hydroxyl-L-arginine.	2003-09-01	12921781
Two modes of binding of N-hydroxyguanidines to NO synthases: first evidence for the formation of iron-N-hydroxyguanidine complexes and key role of tetrahydrobiopterin in determining the binding mode.	2003-04-08	12667076
pH-dependent stability of sperm whale myoglobin in water-guanidine hydrochloride solutions.	2003-02	12582821
Microperoxidase 8 catalysed nitrogen oxides formation from oxidation of N-hydroxyguanidines by hydrogen peroxide.	2003-01	12492474
[Metalloporphyrin catalyzed biomimetic oxidation potentials: potential uses and applications].	2003	15112438
The novel binding mode of N-alkyl-N'-hydroxyguanidine to neuronal nitric oxide synthase provides mechanistic insights into NO biosynthesis.	2002-11-26	12437343
Involvement of NO in the endothelium-independent relaxing effects of N(omega)-hydroxy-L-arginine and other compounds bearing a C=NOH function in the rat aorta.	2002-11	12388669
Novel substrates for nitric oxide synthases.	2002-09	12110328
EPR and ENDOR characterization of intermediates in the cryoreduced oxy-nitric oxide synthase heme domain with bound L-arginine or N(G)-hydroxyarginine.	2002-08-20	12173923
Oxidation of N-hydroxyguanidines by cytochromes P450 and NO-synthases and formation of nitric oxide.	2002-08	12214669
Electrochemical and peroxidase oxidation study of N'-hydroxyguanidine derivatives as NO donors.	2002-06-03	12031330
Ceramide binding to African-American hair fibre correlates with resistance to hair breakage.	2002-02	18498489
N-hydroxyguanidines as new heme ligands: UV-visible, EPR, and resonance Raman studies of the interaction of various compounds bearing a C=NOH function with microperoxidase-8.	2001-08-21	11502185
Oxidations of N(omega)-hydroxyarginine analogues and various N-hydroxyguanidines by NO synthase II: key role of tetrahydrobiopterin in the reaction mechanism and substrate selectivity.	2001-02	11258969

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:08:08 GMT 2025` Edited by `admin` on `Mon Mar 31 19:08:08 GMT 2025`
Record UNII	8767F421T7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-529357

Preferred Name

English

HYDROXYGUANIDINE

Common Name

English

N-HYDROXYGUANIDINE

Systematic Name

English

UREA, OXIME

Common Name

English

N''-HYDROXYGUANIDINE

Systematic Name

English

GUANIDINE, HYDROXY-

Systematic Name

English

Code System Code Type Description

NSC

529357