CAS 10597-89-4|(2R)-2-{[(2R,3R,4R,5R)-2-acetamido-4,5,6-trihydroxy-1-oxohexan-3-yl]oxy}propanoic acid|NAMA|N-acetylmuramic acid|N-Acetylmuramic acid|MurNAc|2-Acetamido-2-deoxy-3-O-(D-1-carboxyethyl)...

General Information

Structure

Molecular Formula

C₁₁H₁₉NO₈

Molecular Mass

293.27046

Exact Mass

293.11106657

Charge

InChI

InChI=1S/C11H19NO8/c1-5(11(18)19)20-10(9(17)8(16)4-14)7(3-13)12-6(2)15/h3,5,7-10,14,16-17H,4H2,1-2H3,(H,12,15)(H,18,19)/t5-,7+,8-,9-,10-/m1/s1

InChIKey

SOARVSUSWULNDI-TVVSKHENSA-N

Canonic Smiles

O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O[C@@H](C(=O)O)C)NC(=O)C

Isomeric Smiles

C[C@H](C(=O)O)O[C@H]([C@H](C=O)NC(=O)C)[C@@H]([C@@H](CO)O)O

Calculated Properties

JChem

LogD (pH = 7.4)

-6.51

LogD (pH = 5.5)

-5.06

Log P

-3.17

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

3.60

Polar Surface Area

153.39

Polarizability

27.16

Molar Refractivity

63.78

LOG S

-0.08

Data Source

Commercial Catalog

Academic Data

Data Source

Names and Identifiers

IUPAC Traditional name

N-acetylmuramic acid aldehydo-N-acetylmuramic acid

Synonyms

N-Acetylmuramic acidNAMA2-Acetamido-2-deoxy-3-O-(D-1-carboxyethyl)-D-glucopyranoseMurNAc(R)-2-(Acetylamino)-3-O-(1-carboxyethyl)-2-deoxy-D-glucose(+)-N-乙酰胞壁酸N-Acetylmuramic acidN-乙酰基-2-葡糖胺-3-乳酸醚2-乙酰胺基-2-脱氧-3-O-(D-1-羧基乙基)-D-吡喃葡萄糖N-乙酰胞壁酸(+)-N-Acetylmuramic acidaldehydo-N-acetylmuramic acid(R)-2-acetamido-3-O-(1-carboxyethyl)-2-deoxy-D-glucoseN-acetylmuramic acid

IUPAC name

(2R)-2-{[(2R,3R,4R,5R)-2-acetamido-4,5,6-trihydroxy-1-oxohexan-3-yl]oxy}propanoic acid

Names and Identifiers

Registration numbers

CAS Number

10597-89-4

Beilstein Number

19942457008215

MDL Number

MFCD00221511

PubChem SID

2489071416222758846530769

PubChem CID

82756

UniProt Database

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

ACToR Database

CompTox Database

SABIO-RK Database

SureChEMBL Database

CHEBI ID

EnzymePortal Database

P75949

Registration numbers

Properties

Physical Property

[α]23/D +65°, c = 0.1 in H2O

[α]20/D +41±2°, 24 hr, c = 1.5% in H2O

125 °C (dec.)(lit.)

~125 °C (dec.)

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Sigma Aldrich

01355

Other Notes
MurNAc inhibits the adsorbtion of the bactriocin smegmatocin 14468, to intact Mycobacterium diernhoferi ATCC 19340 cells1

A3007

包装
10, 50, 100, 500 mg in glass bottle
Application
N-Acetylmuramic acid (NAMA), a lactic acid ether derivative of N-acetylglucosamine found in bacterial cell wall proteoglycans, is used as a substrate to identify, differentiate and characterize N-acetylmuramic acid/N-acetylglucosamine kinase(s) and N-acetylmuramic acid etherase(s).

Molecule

ID:133311