ChemFOnt: Showing chemical card for Neu5Ac(2->3)Gal(1->4)GlcNAc(1->2) Man(1->3)Neu5Ac(2->3)Gal(1->4)GlcNAc(1->2)Man(1->6)Man(1->4)GlcNAc(1->4)GlcNAc (CFc000002857)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:50 UTC

Chemfont ID

CFc000002857

Molecule Identification

Common Name

Neu5Ac(2->3)Gal(1->4)GlcNAc(1->2) Man(1->3)Neu5Ac(2->3)Gal(1->4)GlcNAc(1->2)Man(1->6)Man(1->4)GlcNAc(1->4)GlcNAc

Definition

Neu5Ac(2->3)Gal(1->4)GlcNAc(1->2) Man(1->3)Neu5Ac(2->3)Gal(1->4)GlcNAc(1->2)Man(1->6)Man(1->4)GlcNAc(1->4)GlcNAc is a glycan that has been found in proteins derived from human fibrinogen, in human serum alpha-fetoprotein, in Inter-alpha-inhibitor (I-alpha-I is a serine proteinase inhibitor found in high concentartions in human plasma), in human alpha1-acid glycoprotein and many others. (PMID: 16013856 , 10584881 , 9425062 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value

Source

O-(N-Acetyl-alpha-neuraminosyl)-[2->3(or 2->6)]-O-beta-D-galactopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->2)-O-alpha-D-mannopyranosyl-(1->3)-O-[O-(N-acetyl-alpha-neuraminosyl)-[2->3(or 2->6)]-O-beta-D-galactopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->2)-alpha-D-mannopyranosyl-(1->6)]-O-beta-D-mannopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->4)-2-(acetylamino)-2-deoxy- D-glucose

HMDB

(2S,4S,5R,6R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6S)-6-{[(2S,3S,4S,5S,6R)-2-{[(2R,3R,4S,5S,6S)-4-{[(2R,3S,4S,5S,6R)-3-{[(2S,3R,4R,5S,6R)-5-{[(2S,3R,4S,5S,6R)-4-{[(2S,4S,5R,6R)-2-carboxy-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6S)-6-{[(2R,3S,4R,5R)-4,6-dihydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-3-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxyoxan-2-yl]methoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

HMDB

Chemical Formula

C₈₄H₁₃₈N₆O₆₂

Average Molecular Weight

2223.9975

Monoisotopic Molecular Weight

2222.78300501

IUPAC Name

(2S,4S,5R,6R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6S)-6-{[(2S,3S,4S,5S,6R)-2-{[(2R,3R,4S,5S,6S)-4-{[(2R,3S,4S,5S,6R)-3-{[(2S,3R,4R,5S,6R)-5-{[(2S,3R,4S,5S,6R)-4-{[(2S,4S,5R,6R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-acetamido-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6S)-5-acetamido-6-{[(2R,3S,4R,5R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxyoxan-2-yl]methoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-5-acetamido-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

Traditional Name

(2S,4S,5R,6R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6S)-6-{[(2S,3S,4S,5S,6R)-2-{[(2R,3R,4S,5S,6S)-4-{[(2R,3S,4S,5S,6R)-3-{[(2S,3R,4R,5S,6R)-5-{[(2S,3R,4S,5S,6R)-4-{[(2S,4S,5R,6R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-acetamido-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6S)-5-acetamido-6-{[(2R,3S,4R,5R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxyoxan-2-yl]methoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-5-acetamido-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

CAS Registry Number

145211-77-4

SMILES

[H][C@]1(O[C@@](C[C@H](O)[C@H]1NC(C)=O)(O[C@H]1[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]2[C@H](O)[C@@H](NC(C)=O)[C@H](O[C@H]3[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]3OC[C@H]3O[C@@H](O[C@H]4[C@H](O)[C@@H](NC(C)=O)[C@H](O[C@H]5[C@H](O)[C@@H](NC(C)=O)C(O)O[C@@H]5CO)O[C@@H]4CO)[C@@H](O)[C@@H](O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]4O[C@@H]4O[C@H](CO)[C@@H](O[C@@H]5O[C@H](CO)[C@H](O)[C@H](O[C@@]6(C[C@H](O)[C@@H](NC(C)=O)[C@@]([H])(O6)[C@H](O)[C@H](O)CO)C(O)=O)[C@H]5O)[C@H](O)[C@H]4NC(C)=O)[C@@H]3O)O[C@@H]2CO)[C@@H]1O)C(O)=O)[C@H](O)[C@H](O)CO

InChI Identifier

InChI=1S/C84H138N6O62/c1-20(101)85-39-26(107)7-83(81(128)129,149-65(39)45(111)28(109)9-91)151-68-49(115)32(13-95)134-77(59(68)125)144-63-36(17-99)139-74(43(54(63)120)89-24(5)105)147-70-56(122)47(113)30(11-93)136-79(70)132-19-38-51(117)67(58(124)76(141-38)143-62-35(16-98)138-73(42(53(62)119)88-23(4)104)142-61-34(15-97)133-72(127)41(52(61)118)87-22(3)103)146-80-71(57(123)48(114)31(12-94)137-80)148-75-44(90-25(6)106)55(121)64(37(18-100)140-75)145-78-60(126)69(50(116)33(14-96)135-78)152-84(82(130)131)8-27(108)40(86-21(2)102)66(150-84)46(112)29(110)10-92/h26-80,91-100,107-127H,7-19H2,1-6H3,(H,85,101)(H,86,102)(H,87,103)(H,88,104)(H,89,105)(H,90,106)(H,128,129)(H,130,131)/t26-,27-,28+,29+,30+,31+,32+,33+,34+,35+,36+,37+,38+,39+,40+,41+,42+,43+,44+,45+,46+,47+,48+,49-,50-,51+,52+,53+,54+,55+,56-,57-,58-,59+,60+,61+,62+,63+,64+,65+,66+,67-,68-,69-,70-,71-,72?,73-,74-,75-,76-,77-,78-,79-,80+,83-,84-/m0/s1

InChI Key

RDUPXSKIKTZZLY-FKVHUISKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Oligosaccharides

Alternative Parents

Substituents

Oligosaccharide
O-glycosyl compound
Glycosyl compound
Oxane
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0006625)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	186 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-23	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	2.54	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	62	ChemAxon
Hydrogen Donor Count	39	ChemAxon
Polar Surface Area	1070.16 Å²	ChemAxon
Rotatable Bond Count	43	ChemAxon
Refractivity	460.18 m³·mol⁻¹	ChemAxon
Polarizability	211.64 Å³	ChemAxon
Number of Rings	11	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

HMDB0006625

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB024012

KNApSAcK ID

Not Available

Chemspider ID

9084725

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10909468

PDB ID

Not Available

ChEBI ID

154383

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Neu5Ac(2->3)Gal(1->4)GlcNAc(1->2) Man(1->3)Neu5Ac(2->3)Gal(1->4)GlcNAc(1->2)Man(1->6)Man(1->4)GlcNAc(1->4)GlcNAc (CFc000002857)

MOL for CFc000002857 (Neu5Ac(2->3)Gal(1->4)GlcNAc(1->2) Man(1->3)Neu5Ac(2->3)Gal(1->4)GlcNAc(1->2)Man(1->6)Man(1->4)GlcNAc(1->4)GlcNAc)

3D MOL for CFc000002857 (Neu5Ac(2->3)Gal(1->4)GlcNAc(1->2) Man(1->3)Neu5Ac(2->3)Gal(1->4)GlcNAc(1->2)Man(1->6)Man(1->4)GlcNAc(1->4)GlcNAc)

3D SDF for CFc000002857 (Neu5Ac(2->3)Gal(1->4)GlcNAc(1->2) Man(1->3)Neu5Ac(2->3)Gal(1->4)GlcNAc(1->2)Man(1->6)Man(1->4)GlcNAc(1->4)GlcNAc)

3D-SDF for CFc000002857 (Neu5Ac(2->3)Gal(1->4)GlcNAc(1->2) Man(1->3)Neu5Ac(2->3)Gal(1->4)GlcNAc(1->2)Man(1->6)Man(1->4)GlcNAc(1->4)GlcNAc)

PDB for CFc000002857 (Neu5Ac(2->3)Gal(1->4)GlcNAc(1->2) Man(1->3)Neu5Ac(2->3)Gal(1->4)GlcNAc(1->2)Man(1->6)Man(1->4)GlcNAc(1->4)GlcNAc)

3D PDB for CFc000002857 (Neu5Ac(2->3)Gal(1->4)GlcNAc(1->2) Man(1->3)Neu5Ac(2->3)Gal(1->4)GlcNAc(1->2)Man(1->6)Man(1->4)GlcNAc(1->4)GlcNAc)

SMILES for CFc000002857 (Neu5Ac(2->3)Gal(1->4)GlcNAc(1->2) Man(1->3)Neu5Ac(2->3)Gal(1->4)GlcNAc(1->2)Man(1->6)Man(1->4)GlcNAc(1->4)GlcNAc)

INCHI for CFc000002857 (Neu5Ac(2->3)Gal(1->4)GlcNAc(1->2) Man(1->3)Neu5Ac(2->3)Gal(1->4)GlcNAc(1->2)Man(1->6)Man(1->4)GlcNAc(1->4)GlcNAc)

Structure for CFc000002857 (Neu5Ac(2->3)Gal(1->4)GlcNAc(1->2) Man(1->3)Neu5Ac(2->3)Gal(1->4)GlcNAc(1->2)Man(1->6)Man(1->4)GlcNAc(1->4)GlcNAc)

3D Structure for CFc000002857 (Neu5Ac(2->3)Gal(1->4)GlcNAc(1->2) Man(1->3)Neu5Ac(2->3)Gal(1->4)GlcNAc(1->2)Man(1->6)Man(1->4)GlcNAc(1->4)GlcNAc)