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3554-93-6 molecular structure
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N-[2-(benzyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

ChemBase ID: 132684
Molecular Formular: C15H21NO6
Molecular Mass: 311.33034
Monoisotopic Mass: 311.1368874
SMILES and InChIs

SMILES:
CC(=O)NC1C(C(C(OC1OCc1ccccc1)CO)O)O
Canonical SMILES:
OCC1OC(OCc2ccccc2)C(C(C1O)O)NC(=O)C
InChI:
InChI=1S/C15H21NO6/c1-9(18)16-12-14(20)13(19)11(7-17)22-15(12)21-8-10-5-3-2-4-6-10/h2-6,11-15,17,19-20H,7-8H2,1H3,(H,16,18)
InChIKey:
SKOZFDIGKDPQBO-UHFFFAOYSA-N

Cite this record

CBID:132684 http://www.chembase.cn/molecule-132684.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
N-[2-(benzyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
IUPAC Traditional name
N-[2-(benzyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Synonyms
α-D-GalNAc-1→OCH2Ph
Benzyl N-acetyl-α-D-galactosaminide
Benzyl-α-GalNAc
GalNAc α-O-benzyl
GalNAc-O-bn
Benzyl 2-acetamido-2-deoxy-α-D-galactopyranoside
CAS Number
3554-93-6
MDL Number
MFCD00057920
PubChem SID
24891802
162226961
PubChem CID
561184

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Sigma Aldrich
B4894 external link Add to cart Please log in.
Data Source Data ID
PubChem 561184 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 12.357337  H Acceptors
H Donor LogD (pH = 5.5) -0.8529751 
LogD (pH = 7.4) -0.8529792  Log P -0.8529748 
Molar Refractivity 76.3885 cm3 Polarizability 30.718012 Å3
Polar Surface Area 108.25 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Safety Information Bioassay(PubChem)
German water hazard class
3 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

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - B4894 external link
Application
Benzyl 2-acetamido-2-deoxy-α-D-galactopyranoside (BADGP), an O-GlcNAc (OGT) transferase inhibitor, is used to study the physiological effects of O-glycosylation modulation.
Biochem/physiol Actions
Benzyl-N-acetyl-α-galactosaminide inhibits glycosyltransferase incorporation of glucosamine into O-glycans. Suppresses mucin biosynthesis1,2 and inhibits MUC1 expression in breast cancer cell line MDF-7.3

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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