ContaminantDB: Difucosyllacto-N-hexaose

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 07:18:34 UTC

Update Date

2016-11-09 01:21:27 UTC

Accession Number

CHEM036194

Identification

Common Name

Difucosyllacto-N-hexaose

Class

Small Molecule

Description

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Propenyl O-6-deoxy-alpha-L-galactopyranosyl-(1->4)-O-[beta-D-galactopyranosyl-(1->3)]-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-[O-6-deoxy-alpha-L-galactopyranosyl-(1->3)-O-[beta-D-galactopyranosyl-(1->4)]-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->6)]-O-beta-D-galactopyranosyl-(1->4)-beta-D-glucopyranoside	HMDB
2-Propenyl O-6-deoxy-alpha-L-galactopyranosyl-(1->4)-O-[beta-delta-galactopyranosyl-(1->3)]-O-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->3)-O-[O-6-deoxy-alpha-L-galactopyranosyl-(1->3)-O-[beta-delta-galactopyranosyl-(1->4)]-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->6)]-O-beta-delta-galactopyranosyl-(1->4)-beta-delta-glucopyranoside	HMDB
N-[(2R,3R,4R,5S,6R)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-4-{[(2S,3R,4R,5S,6R)-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-2-yl]methoxy}-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]ethanimidate	HMDB
Difucosyllacto-N-hexaose	MeSH

Chemical Formula

C₅₂H₈₈N₂O₃₉

Average Molecular Mass

1365.245 g/mol

Monoisotopic Mass

1364.496 g/mol

CAS Registry Number

210427-13-7

IUPAC Name

N-[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4S,5R,6S)-2-({[(2R,3R,4R,5S,6R)-3-acetamido-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-3,5-dihydroxy-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]acetamide

Traditional Name

SMILES

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

InChI Identifier

InChI=1S/C52H88N2O39/c1-11-23(62)28(67)34(73)48(80-11)89-41-19(9-59)86-47(22(54-14(4)61)43(41)92-51-37(76)31(70)26(65)16(6-56)84-51)93-44-27(66)20(87-52(38(44)77)88-39-17(7-57)82-45(78)33(72)32(39)71)10-79-46-21(53-13(3)60)42(91-49-35(74)29(68)24(63)12(2)81-49)40(18(8-58)85-46)90-50-36(75)30(69)25(64)15(5-55)83-50/h11-12,15-52,55-59,62-78H,5-10H2,1-4H3,(H,53,60)(H,54,61)/t11-,12-,15-,16-,17-,18-,19-,20-,21-,22-,23+,24+,25+,26+,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+/m1/s1

InChI Key

SUSQQDGHFAOUBW-PVLJGHBYSA-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
N-acyl-alpha-hexosamine
Glycosyl compound
O-glycosyl compound
Oxane
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Polyol
Organopnictogen compound
Primary alcohol
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	181 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-14	ChemAxon
logS	-0.88	ALOGPS
pKa (Strongest Acidic)	11.08	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	39	ChemAxon
Hydrogen Donor Count	24	ChemAxon
Polar Surface Area	641.71 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	281.93 m³·mol⁻¹	ChemAxon
Polarizability	129.66 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f7a-4977000000-3d80053cdd4cdd2cedec	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-9742001010-fd58769a2e96fd880ac1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4s-9622000000-7409ce651cf5cbeb8137	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f92-2497210020-a13ed109b78f7711e476	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f92-0926011323-a323286cdcf62a5e48d8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-070i-2410090602-7143c204fe4f7ba20acd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0209000000-6e4b32df4c5b3dc611a5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-7569000000-6091eab3d30212af4a48	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f79-9111000000-bc73575371d493bd1494	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-3392000000-9f51707aa62512d7aa4c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-066s-9678000000-586931410a56fdf2fd94	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02tm-9352000000-d3a47f1137a6c0a16fad	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0006694

FooDB ID

FDB024027

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

8139457

ChEBI ID

Not Available

PubChem Compound ID

9963863

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Kim, Hyunjin M.; Kim, In Jong; Danishefsky, Samuel J. Total Syntheses of Tumor-Related Antigens N3: Probing the Feasibility Limits of the Glycal Assembly Method. Journal of the American Chemical Society (2001), 123(1), 35-48.

2. Nakajima K, Kinoshita M, Matsushita N, Urashima T, Suzuki M, Suzuki A, Kakehi K: Capillary affinity electrophoresis using lectins for the analysis of milk oligosaccharide structure and its application to bovine colostrum oligosaccharides. Anal Biochem. 2006 Jan 1;348(1):105-14. Epub 2005 Oct 26.

3. Kim HM, Kim IJ, Danishefsky SJ: Total syntheses of tumor-related antigens N3: probing the feasibility limits of the glycal assembly method. J Am Chem Soc. 2001 Jan 10;123(1):35-48.

4. Bruntz R, Dabrowski U, Dabrowski J, Ebersold A, Peter-Katalinic J, Egge H: Fucose-containing oligosaccharides from human milk from a donor of blood group 0 Le(a) nonsecretor. Biol Chem Hoppe Seyler. 1988 Apr;369(4):257-73.

Difucosyllacto-N-hexaose (CHEM036194)

Structure for CHEM036194: Difucosyllacto-N-hexaose