ChemFOnt: Showing chemical card for 9-O-Acetyl-GD3 (CFc000227141)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:51:57 UTC

Chemfont ID

CFc000227141

Molecule Identification

Common Name

9-O-Acetyl-GD3

Definition

6-[3-(acetyloxy)-1,2-dihydroxypropyl]-2-[(1-{6-carboxy-6-[(2-{[4,5-dihydroxy-6-({3-hydroxy-2-[(1-hydroxyethylidene)amino]octadec-4-en-1-yl}oxy)-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl)oxy]-4-hydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl}-1,3-dihydroxypropan-2-yl)oxy]-4-hydroxy-5-[(1-hydroxyethylidene)amino]oxane-2-carboxylic acid belongs to the class of organic compounds known as glycosphingolipids. These are sphingolipids containing a saccharide moiety glycosidically attached to the sphingoid base. Although saccharide moieties are mostly O-glycosidically linked to the ceramide moiety, other sphingolipids with glycosidic bonds of other types (e.g. S-,C-, or N-type) has been reported. Based on a literature review very few articles have been published on 6-[3-(acetyloxy)-1,2-dihydroxypropyl]-2-[(1-{6-carboxy-6-[(2-{[4,5-dihydroxy-6-({3-hydroxy-2-[(1-hydroxyethylidene)amino]octadec-4-en-1-yl}oxy)-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl)oxy]-4-hydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl}-1,3-dihydroxypropan-2-yl)oxy]-4-hydroxy-5-[(1-hydroxyethylidene)amino]oxane-2-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
6-[3-(Acetyloxy)-1,2-dihydroxypropyl]-2-[(1-{6-carboxy-6-[(2-{[4,5-dihydroxy-6-({3-hydroxy-2-[(1-hydroxyethylidene)amino]octadec-4-en-1-yl}oxy)-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl)oxy]-4-hydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl}-1,3-dihydroxypropan-2-yl)oxy]-4-hydroxy-5-[(1-hydroxyethylidene)amino]oxane-2-carboxylate	Generator

Chemical Formula

C₅₆H₉₅N₃O₃₀

Average Molecular Weight

1290.367

Monoisotopic Molecular Weight

1289.600038671

IUPAC Name

6-[2-({6-[3-(acetyloxy)-1,2-dihydroxypropyl]-2-carboxy-5-acetamido-4-hydroxyoxan-2-yl}oxy)-1,3-dihydroxypropyl]-5-acetamido-2-{[2-({6-[(2-acetamido-3-hydroxyoctadec-4-en-1-yl)oxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl}oxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxyoxane-2-carboxylic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCC=CC(O)C(COC1OC(CO)C(OC2OC(CO)C(O)C(OC3(CC(O)C(NC(C)=O)C(O3)C(O)C(CO)OC3(CC(O)C(NC(C)=O)C(O3)C(O)C(O)COC(C)=O)C(O)=O)C(O)=O)C2O)C(O)C1O)NC(C)=O

InChI Identifier

InChI=1S/C56H95N3O30/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-32(67)31(57-27(2)63)25-82-51-45(75)44(74)47(38(24-62)84-51)85-52-46(76)50(42(72)36(22-60)83-52)89-56(54(79)80)21-34(69)40(59-29(4)65)49(88-56)43(73)37(23-61)86-55(53(77)78)20-33(68)39(58-28(3)64)48(87-55)41(71)35(70)26-81-30(5)66/h18-19,31-52,60-62,67-76H,6-17,20-26H2,1-5H3,(H,57,63)(H,58,64)(H,59,65)(H,77,78)(H,79,80)

InChI Key

ODBNHBMRTCHJEH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycosphingolipids. These are sphingolipids containing a saccharide moiety glycosidically attached to the sphingoid base. Although saccharide moieties are mostly O-glycosidically linked to the ceramide moiety, other sphingolipids with glycosidic bonds of other types (e.G. S-,C-, or N-type) has been reported.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Glycosphingolipids

Direct Parent

Glycosphingolipids

Alternative Parents

Substituents

Glycosphingolipid
Oligosaccharide
Neuraminic acid
Fatty acyl glycoside
C-glucuronide
Alkyl glycoside
C-glycosyl compound
Glycosyl compound
O-glycosyl compound
Tricarboxylic acid or derivatives
Ketal
Fatty acyl
Pyran
Oxane
Carboxylic acid ester
Secondary alcohol
Acetal
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic oxide
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Organopnictogen compound
Carbonyl group
Alcohol
Organonitrogen compound
Organooxygen compound
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.07 g/L	ALOGPS
logP	-0.23	ALOGPS
logP	-3.5	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	2.42	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	29	ChemAxon
Hydrogen Donor Count	18	ChemAxon
Polar Surface Area	525.03 Å²	ChemAxon
Rotatable Bond Count	38	ChemAxon
Refractivity	295.86 m³·mol⁻¹	ChemAxon
Polarizability	132.52 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0247605

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 9-O-Acetyl-GD3 (CFc000227141)

MOL for CFc000227141 (9-O-Acetyl-GD3)

3D MOL for CFc000227141 (9-O-Acetyl-GD3)

3D SDF for CFc000227141 (9-O-Acetyl-GD3)

3D-SDF for CFc000227141 (9-O-Acetyl-GD3)

PDB for CFc000227141 (9-O-Acetyl-GD3)

3D PDB for CFc000227141 (9-O-Acetyl-GD3)

SMILES for CFc000227141 (9-O-Acetyl-GD3)

INCHI for CFc000227141 (9-O-Acetyl-GD3)

Structure for CFc000227141 (9-O-Acetyl-GD3)

3D Structure for CFc000227141 (9-O-Acetyl-GD3)