Nomega-hydroxy-L-arginine

ID: ALA260629

Chembl Id: CHEMBL260629

Cas Number: 53054-07-2

PubChem CID: 123895

Max Phase: Preclinical

Molecular Formula: C6H14N4O3

Molecular Weight: 190.20

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  N=C(NO)NCCC[C@H](N)C(=O)O

Standard InChI:  InChI=1S/C6H14N4O3/c7-4(5(11)12)2-1-3-9-6(8)10-13/h4,13H,1-3,7H2,(H,11,12)(H3,8,9,10)/t4-/m0/s1

Standard InChI Key:  FQWRAVYMZULPNK-BYPYZUCNSA-N

Alternative Forms

  1. Parent:

  2. Alternative Forms:

Associated Targets(Human)

NOS2 Tchem Nitric oxide synthase, inducible (1636 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NFKB1 Tclin Nuclear factor NF-kappa-B p105 subunit (1459 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ARG1 Tchem Arginase-1 (360 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ARG2 Tchem Arginase-2, mitochondrial (9289 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

ARG1 Arginase-1 (70 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chrm1 Muscarinic acetylcholine receptor M1 (3437 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Aorta (2975 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Liver (4264 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Nos2 Nitric oxide synthase, inducible (3573 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
J774.A1 (2436 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Arg1 Arginase-1 (17 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 190.20Molecular Weight (Monoisotopic): 190.1066AlogP: -1.32#Rotatable Bonds: 5
Polar Surface Area: 131.46Molecular Species: ZWITTERIONHBA: 4HBD: 6
#RO5 Violations: 1HBA (Lipinski): 7HBD (Lipinski): 7#RO5 Violations (Lipinski): 1
CX Acidic pKa: 2.20CX Basic pKa: 10.48CX LogP: -3.25CX LogD: -4.78
Aromatic Rings: Heavy Atoms: 13QED Weighted: 0.14Np Likeness Score: 0.96

References

1. Kotthaus J, Schade D, Töpker-Lehmann K, Beitz E, Clement B..  (2008)  N(delta)-Methylated L-arginine derivatives and their effects on the nitric oxide generating system.,  16  (5): [PMID:18083522] [10.1016/j.bmc.2007.11.066]
2. Martin NI, Woodward JJ, Winter MB, Marletta MA..  (2009)  4,4-Difluorinated analogues of l-arginine and N(G)-hydroxy-l-arginine as mechanistic probes for nitric oxide synthase.,  19  (6): [PMID:19230661] [10.1016/j.bmcl.2009.01.076]
3. PubChem BioAssay data set, 
4. Zhang Q, Milliken P, Kulczynska A, Slawin AM, Gordon A, Kirkby NS, Webb DJ, Botting NP, Megson IL..  (2013)  Development and characterization of glutamyl-protected N-hydroxyguanidines as reno-active nitric oxide donor drugs with therapeutic potential in acute renal failure.,  56  (13): [PMID:23782349] [10.1021/jm400146r]
5. Holden JK, Kang S, Hollingsworth SA, Li H, Lim N, Chen S, Huang H, Xue F, Tang W, Silverman RB, Poulos TL..  (2015)  Structure-based design of bacterial nitric oxide synthase inhibitors.,  58  (2): [PMID:25522110] [10.1021/jm501723p]
6. Litty FA, Gudd J, Girreser U, Clement B, Schade D..  (2016)  Design, Synthesis, and Bioactivation of O-Glycosylated Prodrugs of the Natural Nitric Oxide Precursor N(ω)-Hydroxy-l-arginine.,  59  (17): [PMID:27548300] [10.1021/acs.jmedchem.6b00810]
7. Borek B,Gajda T,Golebiowski A,Blaszczyk R.  (2020)  Boronic acid-based arginase inhibitors in cancer immunotherapy.,  28  (18): [PMID:32828425] [10.1016/j.bmc.2020.115658]
8. Zhang J, Zhang Y, Qu B, Yang H, Hu S, Dong X..  (2021)  If small molecules immunotherapy comes, can the prime be far behind?,  218  [PMID:33773287] [10.1016/j.ejmech.2021.113356]