ChemFOnt: Showing chemical card for Sialyllacto-N-neotetraose c (CFc000002834)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:48 UTC

Chemfont ID

CFc000002834

Molecule Identification

Common Name

Sialyllacto-N-neotetraose c

Definition

Sialyllacto-N-neotetraose c is an oligosaccharide found in human breast milk. Two additional sialylated pentasaccharides include sialyllacto-N-tetraose-a and -b. Oligosaccharides containing N-acetyl (or N-glycolyl) neuraminic acid, i.e. sialylated oligosaccharides, are important components of glycoproteins and glycolipids. In nature, sialylated oligosaccharides often occur as homologous series, with incremental differences in composition, and as structural isomers with subtle differences in monosaccharide sequence and glycosyl linkage and, possibly, with presence or absence of molecular branching. A large number of such sialylated oligosaccharides occur in human milk, where they may have important biological functions. Major structural isomers of these acidic oligosaccharides in human milk are 3'- and 6'-sialyllactoses and the sialyllacto-N-tetraoses; appreciable amounts of 3'- and 6'-sialyllactosamines are found in human urine. (PMID:11471815 ). Oligosaccharides in human milk inhibit enteric pathogens in vitro and in vivo. Neutral milk oligosaccharides vary among individuals and over the course of lactation. (PMID:10683228 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
LS-Tetrasaccharide c	HMDB
LSTC	HMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->6)-O-beta-D-galactopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)-D-glucose	HMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->6)-O-beta-delta-galactopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->3)-O-beta-delta-galactopyranosyl-(1->4)-delta-glucose	HMDB
SLNT-c	HMDB
(2R,4S,5R,6R)-2-{[(3R,4S,5R,6S)-6-{[(2R,3S,4R,5R,6S)-6-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate	Generator, HMDB

Chemical Formula

C₃₇H₆₂N₂O₂₉

Average Molecular Weight

998.8842

Monoisotopic Molecular Weight

998.343824032

IUPAC Name

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

Traditional Name

CAS Registry Number

64003-55-0

SMILES

CC(=O)N[C@@H]1[C@@H](O)[C@H](O[C@@H]2OC(CO[C@@]3(C[C@H](O)[C@@H](NC(C)=O)[C@@H](O3)[C@H](O)[C@H](O)CO)C(O)=O)[C@H](O)[C@H](O)[C@H]2O)[C@@H](CO)O[C@H]1O[C@H]1[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)[C@@H]1O

InChI Identifier

InChI=1S/C37H62N2O29/c1-10(45)38-19-12(47)3-37(36(59)60,68-31(19)22(52)14(49)5-41)61-9-18-23(53)26(56)27(57)34(64-18)66-30-17(8-44)63-33(20(25(30)55)39-11(2)46)67-32-24(54)16(7-43)62-35(28(32)58)65-29(15(50)6-42)21(51)13(48)4-40/h4,12-35,41-44,47-58H,3,5-9H2,1-2H3,(H,38,45)(H,39,46)(H,59,60)/t12-,13-,14+,15+,16+,17+,18?,19+,20+,21+,22+,23-,24-,25+,26-,27+,28+,29+,30+,31+,32-,33-,34-,35-,37+/m0/s1

InChI Key

SXMGGNXBTZBGLU-IBUUTZGMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

N-acylneuraminic acids

Alternative Parents

Substituents

Oligosaccharide
N-acylneuraminic acid
Neuraminic acid
Fatty acyl glycoside
N-acyl-alpha-hexosamine
C-glucuronide
Alkyl glycoside
C-glycosyl compound
Glycosyl compound
O-glycosyl compound
Ketal
Beta-hydroxy aldehyde
Fatty acyl
Pyran
Oxane
Acetamide
Alpha-hydroxyaldehyde
Carboxamide group
Secondary alcohol
Secondary carboxylic acid amide
Polyol
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Acetal
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organonitrogen compound
Carbonyl group
Hydrocarbon derivative
Primary alcohol
Aldehyde
Organic nitrogen compound
Organopnictogen compound
Organic oxide
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

Breast milk (PMID: 10683228)
Breast milk (HMDB: HMDB0006593)

Source

Endogenous

Endogenous (HMDB: HMDB0006593)

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	62.6 g/L	ALOGPS
logP	-3.2	ALOGPS
logP	-12	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	2.89	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	29	ChemAxon
Hydrogen Donor Count	19	ChemAxon
Polar Surface Area	510.09 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	205.96 m³·mol⁻¹	ChemAxon
Polarizability	94.04 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

HMDB0006593

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023990

KNApSAcK ID

Not Available

Chemspider ID

58145732

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477861

PDB ID

Not Available

ChEBI ID

89905

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Murakami, Tatsuya; Suzawa, Toshiyuki; Yamazaki, Motoo; Sato, Mitsuo; Endo, Tetsuo; Koizumi, Satoshi; Imada, Teruyoshi. Screening of compounds with specific site affinity, probes for the process, and use of oligosaccharides for drug delivery, diagnostic agents, and pharmaceuticals. Jpn. Kokai Tokkyo Koho (2004), 25 pp. CODEN: JKXXAF JP 2004138397 A 20040513 CAN 140:386061 AN 2004:391539

Showing chemical card for Sialyllacto-N-neotetraose c (CFc000002834)

MOL for CFc000002834 (Sialyllacto-N-neotetraose c)

3D MOL for CFc000002834 (Sialyllacto-N-neotetraose c)

3D SDF for CFc000002834 (Sialyllacto-N-neotetraose c)

3D-SDF for CFc000002834 (Sialyllacto-N-neotetraose c)

PDB for CFc000002834 (Sialyllacto-N-neotetraose c)

3D PDB for CFc000002834 (Sialyllacto-N-neotetraose c)

SMILES for CFc000002834 (Sialyllacto-N-neotetraose c)

INCHI for CFc000002834 (Sialyllacto-N-neotetraose c)

Structure for CFc000002834 (Sialyllacto-N-neotetraose c)

3D Structure for CFc000002834 (Sialyllacto-N-neotetraose c)