ChemFOnt: Showing chemical card for Muramic acid (CFc000001818)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:33 UTC

Chemfont ID

CFc000001818

Molecule Identification

Common Name

Muramic acid

Definition

Muramic acid is an amino sugar acid. In terms of chemical composition, it is the ether of lactic acid and glucosamine. It occurs naturally as N-acetylmuramic acid in peptidoglycan, whose primary function is a structural component of many typical bacterial cell walls. Muramic acid, also known as muramate or murexide, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. Muramic acid is an amino sugar acid. It occurs naturally as N-acetylmuramic acid in peptidoglycan, whose primary function is a structural component of many typical bacterial cell walls. In terms of chemical composition, it is the ether of lactic acid and glucosamine.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Muramate	Generator
(+)-Muramate	HMDB
(+)-Muramic acid	HMDB
3-O-alpha-Carboxyethyl-D-glucosamine	HMDB
3-O-alpha-Carboxyethyl-delta-glucosamine	HMDB
Muramic acid hydrate	HMDB
Murexide	HMDB
(2R)-2-{[(2R,3R,4S,5S,6R)-3-amino-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoate	Generator, HMDB

Chemical Formula

C₉H₁₇NO₇

Average Molecular Weight

251.2338

Monoisotopic Molecular Weight

251.100501903

IUPAC Name

(2R)-2-{[(2R,3R,4S,5S,6R)-3-amino-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid

Traditional Name

(2R)-2-{[(2R,3R,4S,5S,6R)-3-amino-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid

CAS Registry Number

1114-41-6

SMILES

C[C@@H](O[C@H]1[C@@H](N)[C@H](O)O[C@H](CO)[C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C9H17NO7/c1-3(8(13)14)16-7-5(10)9(15)17-4(2-11)6(7)12/h3-7,9,11-12,15H,2,10H2,1H3,(H,13,14)/t3-,4-,5-,6-,7+,9-/m1/s1

InChI Key

MSFSPUZXLOGKHJ-LEISLEKSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Sugar acids and derivatives

Alternative Parents

Substituents

Muramic_acid
Hexose monosaccharide
Amino saccharide
Sugar acid
Monosaccharide
Oxane
Amino acid or derivatives
Hemiacetal
Amino acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Amine
Carbonyl group
Hydrocarbon derivative
Organonitrogen compound
Alcohol
Primary alcohol
Primary amine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Spleen (HMDB: HMDB0003254)

Cellular substructure

Cytoplasm (HMDB: HMDB0003254)

Source

Exogenous

Exogenous (HMDB: HMDB0003254)

Endogenous

Microbe

Microbe (HMDB: HMDB0003254)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	152 g/L	ALOGPS
logP	-3.1	ALOGPS
logP	-4.6	ChemAxon
logS	-0.22	ALOGPS
pKa (Strongest Acidic)	3.33	ChemAxon
pKa (Strongest Basic)	8.12	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	142.47 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	52.91 m³·mol⁻¹	ChemAxon
Polarizability	23.42 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon