CAS 53308-83-1|N<sup>G</sup>-METHYL-L-ARGININE|(2S)-2-amino-5-(1-methylcarbamimidamido)pentanoic acid; acetic acid|acetic acid; delta-N-methylarginine|NG-Monomethyl-L-arginine acetate salt|N5-(Methy...

General Information

Structure

Molecular Formula

C₉H₂₀N₄O₄

Molecular Mass

248.2795

Exact Mass

248.14845514

Charge

InChI

InChI=1S/C7H16N4O2.C2H4O2/c1-10-7(9)11-4-2-3-5(8)6(12)13;1-2(3)4/h5H,2-4,8H2,1H3,(H,12,13)(H3,9,10,11);1H3,(H,3,4)/t5-;/m0./s1

InChIKey

IKPNWIGTWUZCKM-JEDNCBNOSA-N

Canonic Smiles

CC(=O)O.CNC(=N)NCCC[C@@H](C(=O)O)N

Isomeric Smiles

CNC(=N)NCCC[C@H](N)C(=O)O.CC(=O)O

Calculated Properties

JChem

Acid pKa

2.482201

H Acceptors

H Donor

LogD (pH = 5.5)

-5.788655

LogD (pH = 7.4)

-4.5643816

Log P

-2.8717082

Molar Refractivity

58.6977

Polarizability

18.727592

Polar Surface Area

111.23

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Commercial Catalog

Academic Data

Data Source

Names and Identifiers

Synonyms

N^G-METHYL-L-ARGININENG-Monomethyl-L-arginine acetate saltN5-(Methylamidino)-L-ornithine acetate saltNω-Methyl-L-arginine acetate saltNG-Methyl-L-arginine acetate saltL-NMMAANO 1020Tilarginine AcetateN5-[Imino(methylamino)methyl]-L-ornithine AcetateNG-Monomethyl-L-arginine Acetate

IUPAC name

(2S)-2-amino-5-(1-methylcarbamimidamido)pentanoic acid; acetic acid

IUPAC Traditional name

acetic acid; delta-N-methylarginine

Names and Identifiers

Registration numbers

CAS Number

PubChem CID

PubChem SID

Beilstein Number

MDL Number

Registration numbers

Properties

Product Information

Certificate of Analysis

Download link

Empirical Formula (Hill Notation)

C7H16N4O2 · C2H4O2

Purity

≥98% (TLC)

≥95% (HPLC)

Impurities

≤3.5% water

Pharmacology Properties

Gene Information

human ... NOS1(4842), NOS2(4843), NOS3(4846)mouse ... Nos2(18126)rat ... Nos1(24598), Nos2(24599)

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

MP Biomedicals

02155470

Acetate Salt Endothelium-derived relaxing factor inhibitor.

Sigma Aldrich

M7033

Biochem/physiol Actions
Endothelium-derived relaxing factor inhibitor. Inhibits the generation of NO from arginine.

65825

Other Notes
Endothelium-derived relaxing factor inhibitor1

TRC

M565000

A potent inhibitor of NO synthase of adrenal glands, brain, and vascular endothelial cells.

Molecule Details

References

PubChem Literature

From Data Sources

• Sakuma, I., et al., Proc. Nat. Acad. Sci. USA, 85: 8664 (1988).

• Rees, D.D., et al.: Br. J. Pharmacol., 101, 746 (1990)

• McCall, T.B., et al.: Br. J. Pharmacol., 102, 234 (1990)

• Olken, N.M., et al.: Biochem. and Biophys. Res. Commun., 177, 2, 828 (1991)

References

Bioactivity

PubChem BioAssay

Bioactivity

Data Source

Commercial Catalog

Academic Data

Names and Identifiers

Synonyms

IUPAC name

(2S)-2-amino-5-(1-methylcarbamimidamido)pentanoic acid; acetic acid

IUPAC Traditional name

acetic acid; delta-N-methylarginine

Registration numbers

CAS Number

PubChem CID

PubChem SID

Beilstein Number

MDL Number

Molecule Details

Acetate Salt Endothelium-derived relaxing factor inhibitor.

Sigma Aldrich

M7033

Biochem/physiol Actions
Endothelium-derived relaxing factor inhibitor. Inhibits the generation of NO from arginine.

65825

Other Notes
Endothelium-derived relaxing factor inhibitor1

TRC

M565000

A potent inhibitor of NO synthase of adrenal glands, brain, and vascular endothelial cells.

References

PubChem Literature

From Data Sources

• Sakuma, I., et al., Proc. Nat. Acad. Sci. USA, 85: 8664 (1988).

• Rees, D.D., et al.: Br. J. Pharmacol., 101, 746 (1990)

• McCall, T.B., et al.: Br. J. Pharmacol., 102, 234 (1990)

• Olken, N.M., et al.: Biochem. and Biophys. Res. Commun., 177, 2, 828 (1991)

Bioactivity

PubChem BioAssay

Properties

Product Information

Certificate of Analysis

Download link

Empirical Formula (Hill Notation)

C7H16N4O2 · C2H4O2

Purity

≥98% (TLC)

≥95% (HPLC)

Impurities

≤3.5% water

Pharmacology Properties

Gene Information

human ... NOS1(4842), NOS2(4843), NOS3(4846)mouse ... Nos2(18126)rat ... Nos1(24598), Nos2(24599)

Molecule

ID:104323