NORVALINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C5H11NO2
Molecular Weight	117.1463
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC[C@H](N)C(O)=O

InChI

InChIKey=SNDPXSYFESPGGJ-BYPYZUCNSA-N

InChI=1S/C5H11NO2/c1-2-3-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C5H11NO2
Molecular Weight	117.1463
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Proton-coupled amino acid transporter 1 1 Target ID: CHEMBL1914279 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21955456	Interacts 323		46.0 mM [Ki]

PubMed

Title	Date	PubMed
Macrophage arginase promotes tumor cell growth and suppresses nitric oxide-mediated tumor cytotoxicity.	2001 Feb 1	11221839
Human ornithine transcarbamylase: crystallographic insights into substrate recognition and conformational changes.	2001 Mar 15	11237854
Conversion of a glutamate dehydrogenase into methionine/norleucine dehydrogenase by site-directed mutagenesis.	2001 Nov	11722565
Sulfamide antifolates inhibiting thymidylate synthase: synthesis, enzyme inhibition and cytotoxicity.	2002	12362982
Resistance and susceptibility to Marek's disease: nitric oxide synthase/arginase activity balance.	2002 May 1	11900957
Kinetic analysis of phenylalanine dehydrogenase mutants designed for aliphatic amino acid dehydrogenase activity with guidance from homology-based modelling.	2003 Dec	14622249
Arginine deprivation and tumour cell death: arginase and its inhibition.	2003 Feb	12701828
Changes in the ornithine cycle following ionising radiation cause a cytotoxic conditioning of the culture medium of H35 hepatoma cells.	2003 Feb 10	12569390
Two new cyclosporin folds observed in the structures of the immunosuppressant cyclosporin G and the formyl peptide receptor antagonist cyclosporin H at ultra-high resolution.	2003 May 7	12926274
Consumption of L-arginine mediated by Entamoeba histolytica L-arginase (EhArg) inhibits amoebicidal activity and nitric oxide production by activated macrophages.	2003 Nov-Dec	15053781
Arginase pathway in human endothelial cells in pathophysiological conditions.	2004 Aug	15276021
Thrombin stimulates human endothelial arginase enzymatic activity via RhoA/ROCK pathway: implications for atherosclerotic endothelial dysfunction.	2004 Dec 14	15569838
High glucose augments arginase activity and nitric oxide production in the renal cortex.	2004 Jul	15254879
Arginase activity in a murine macrophage cell line (RAW264.7) stimulated with lipopolysaccharide from Actinobacillus actinomycetemcomitans.	2006 Jun	16626370
Intricate knots in proteins: Function and evolution.	2006 Sep 15	16978047
Enzymatic evidence for the key role of arginine in nitrogen translocation by arbuscular mycorrhizal fungi.	2007 Jun	17142485
Structural and evolutionary bioinformatics of the SPOUT superfamily of methyltransferases.	2007 Mar 5	17338813
The crystal structures of ornithine carbamoyltransferase from Mycobacterium tuberculosis and its ternary complex with carbamoyl phosphate and L-norvaline reveal the enzyme's catalytic mechanism.	2008 Jan 25	18062991
Molecular evolution of B6 enzymes: binding of pyridoxal-5'-phosphate and Lys41Arg substitution turn ribonuclease A into a model B6 protoenzyme.	2008 Jun 19	18565210
A 3(10)-helical pentapeptide in water: interplay of alpha,alpha-disubstituted amino acids and the central residue on structure formation.	2009	19489061
Kinetic and thermodynamic control in the stereoselective formation of trans- and cis-2-ferrocenyl-3-pivaloyl-4-alkyl-1,3-oxazolidin-5-ones.	2009 Feb 7	19156318
Inhibition of S6K1 accounts partially for the anti-inflammatory effects of the arginase inhibitor L-norvaline.	2009 Mar 13	19284655
Glutathione-supported arsenate reduction coupled to arsenolysis catalyzed by ornithine carbamoyl transferase.	2009 Sep 1	19248796
Specificities of olfactory receptor neuron responses to amino acids in the black bullhead catfish (Ameiurus melas).	2010 Feb	19756721
Caloric restriction reverses high-fat diet-induced endothelial dysfunction and vascular superoxide production in C57Bl/6 mice.	2010 May	20512454
RNAi-mediated suppression of isoprene emission in poplar transiently impacts phenolic metabolism under high temperature and high light intensities: a transcriptomic and metabolomic analysis.	2010 Sep	20526857

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:31:25 GMT 2023` Edited by `admin` on `Fri Dec 15 16:31:25 GMT 2023`
Record UNII	A70UKS48FE
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NORVALINE

Official Name

English

Norvaline [WHO-DD]

Common Name

English

(S)-2-AMINOVALERIC ACID

Systematic Name

English

(S)-2-AMINOPENTANOIC ACID

Systematic Name

English

(S)-(+)-2-AMINOPENTANOIC ACID

Systematic Name

English

L-.ALPHA.-AMINOVALERIC ACID

Common Name

English

L-NORVALINE

Systematic Name

English

NORVALINE [MI]

Common Name

English

NORVALINE [INCI]

Common Name

English

NSC-203786

Code

English

NORVALINE, L-

Systematic Name

English

2S-AMINOVALERIC ACID

Common Name

English

Classification Tree Code System Code

DSLD

1076 (Number of products:82)