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131-48-6 molecular structure
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(2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

ChemBase ID: 153319
Molecular Formular: C11H19NO9
Molecular Mass: 309.26986
Monoisotopic Mass: 309.10598119
SMILES and InChIs

SMILES:
CC(=O)N[C@@H]1[C@H](C[C@](O[C@H]1[C@@H]([C@@H](CO)O)O)(C(=O)O)O)O
Canonical SMILES:
OC[C@H]([C@H]([C@@H]1O[C@@](O)(C[C@@H]([C@H]1NC(=O)C)O)C(=O)O)O)O
InChI:
InChI=1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11-/m0/s1
InChIKey:
SQVRNKJHWKZAKO-PFQGKNLYSA-N

Cite this record

CBID:153319 http://www.chembase.cn/molecule-153319.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
IUPAC Traditional name
β-neu5ac
Synonyms
(-)-N-Acetylneuraminic acid
NAN
NANA
5-Acetamido-3,5-dideoxy-D-glycero-D-galactononulosonic acid
Lactaminic acid
Sialic acid
N-Acetylneuraminic acid
5-(Acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonic Acid
N-Acetylsialic Acid
N-Acetylneuraminic Acid
醋纽拉酸
N-乙酰甘露糖胺丙酮酸
唾液酸
N-乙酰神经氨酸
CAS Number
131-48-6
EC Number
205-023-1
MDL Number
MFCD00006620
Beilstein Number
1716283
PubChem SID
24888394
24890650
24891482
162247458
24890457
PubChem CID
445063

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 2.996658  H Acceptors
H Donor LogD (pH = 5.5) -6.029575 
LogD (pH = 7.4) -7.0390115  Log P -3.5639374 
Molar Refractivity 63.7814 cm3 Polarizability 26.256002 Å3
Polar Surface Area 176.78 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
5% Solution in Water expand Show data source
Apperance
synthetic, crystalline expand Show data source
White to Off-White Solid expand Show data source
Melting Point
>187°C (dec.) expand Show data source
184-186 °C (dec.)(lit.) expand Show data source
Optical Rotation
[α]24/D -32.0°, c = 1 in H2O expand Show data source
Storage Condition
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H319 expand Show data source
GHS Precautionary statements
P305 + P351 + P338 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
-20°C expand Show data source
Purity
≥95% expand Show data source
≥98% expand Show data source
≥98.0% (TLC) expand Show data source
≥99% expand Show data source
97% expand Show data source
Certificate of Analysis
Download expand Show data source
Biological Source
from Escherichia coli expand Show data source
from sheep submaxillary gland expand Show data source
synthetic expand Show data source
Type
Type IV-S expand Show data source
Type VI expand Show data source
Type VIII expand Show data source
Quality Level
PREMIUM expand Show data source
Shipped in
wet ice expand Show data source
Quality
synthetic expand Show data source
Empirical Formula (Hill Notation)
C11H19NO9 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - A9646 external link
Biochem/physiol Actions
Both sialic acid and neuraminic acid are loosely used to refer to conjugates of neuraminic acid. N-Acetylneuraminic acid is often found as the terminal sugar of cell surface glycoproteins. Cell surface glycoproteins have important roles in cell recognition and interaction as well as in cell adhesion. Membrane glycoproteins are also important in tumor growth and metastases.
Sigma Aldrich - 855650 external link
Packaging
100 mg in glass bottle
Application
N-Acetylneuraminic acid (NANA, Neu5Ac) is a major component of glycoconjugates such as glycolipids, glycoproteins and proteoglycans (sialogylcoproteins) where it confers selective binding characteristics to the glycosylated component. Neu5Ac is used to study its biochemistry, metabolism and uptake in vivo and in vitro. Neu5Ac is used in the development of nanocarriers.
Sigma Aldrich - A0812 external link
Biochem/physiol Actions
Both sialic acid and neuraminic acid are loosely used to refer to conjugates of neuraminic acid. N-Acetylneuraminic acid is often found as the terminal sugar of cell surface glycoproteins. Cell surface glycoproteins have important roles in cell recognition and interaction as well as in cell adhesion. Membrane glycoproteins are also important in tumor growth and metastases.
Application
N-Acetylneuraminic acid (NANA, Neu5Ac) is a major component of glycoconjugates such as glycolipids, glycoproteins and proteoglycans (sialogylcoproteins) where it confers selective binding characteristics to the glycosylated component. Neu5Ac is used to study its biochemistry, metabolism and uptake in vivo and in vitro. Neu5Ac is used in the development of nanocarriers.
Sigma Aldrich - A2388 external link
Biochem/physiol Actions
Both sialic acid and neuraminic acid are loosely used to refer to conjugates of neuraminic acid. N-Acetylneuraminic acid is often found as the terminal sugar of cell surface glycoproteins. Cell surface glycoproteins have important roles in cell recognition and interaction as well as in cell adhesion. Membrane glycoproteins are also important in tumor growth and metastases.
Packaging
10 mg in autosmp vl
Application
N-Acetylneuraminic acid (NANA, Neu5Ac) is a major component of glycoconjugates such as glycolipids, glycoproteins and proteoglycans (sialogylcoproteins) where it confers selective binding characteristics to the glycosylated component. Neu5Ac is used to study its biochemistry, metabolism and uptake in vivo and in vitro. Neu5Ac is used in the development of nanocarriers.
Sigma Aldrich - 01401 external link
Biochem/physiol Actions
Both sialic acid and neuraminic acid are loosely used to refer to conjugates of neuraminic acid. N-Acetylneuraminic acid is often found as the terminal sugar of cell surface glycoproteins. Cell surface glycoproteins have important roles in cell recognition and interaction as well as in cell adhesion. Membrane glycoproteins are also important in tumor growth and metastases.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Methods Enzymol., 5, 391 (1962)
  • • Biochemistry, 18, 2086 (1979)
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PATENTS

PATENTS

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INTERNET

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