Milk Composition Database: Showing metabocard for Disialyllactose (BMDB0006692)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:24:50 UTC

Update Date

2020-06-04 20:48:11 UTC

MCDB ID

BMDB0006692

Secondary Accession Numbers

BMDB06692

Metabolite Identification

Common Name

Disialyllactose

Description

Disialyllactose belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent. Disialyllactose is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
a-Neu5ac-(2->8)-a-neu5ac-(2->3)-b-D-gal-(1->4)-D-GLC	HMDB
alpha-Neu5ac-(2->8)-alpha-neu5ac-(2->3)-beta-D-gal-(1->4)-D-GLC	HMDB
Di-(N-acetylneuramin)lactose	HMDB
O-(N-Acetyl-a-neuraminosyl)-(2->8)-O-(N-acetyl-a-neuraminosyl)-(2->3)-O-b-D-galactopyranosyl-(1->4)-D-glucopyranose	HMDB
O-(N-Acetyl-a-neuraminyl)-(2->8)-O-(N-acetyl-a-neuraminyl)-(2->3)-O-b-D-galactopyranosyl-(1->4)-D-glucopyranose	HMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2-8)-O-(N-acetyl-alpha-neuraminosyl)-(2-3)-O-beta-D-galactopyranosyl-(1-4)- D-glucopyranose	HMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2-8)-O-(N-acetyl-alpha-neuraminosyl)-(2-3)-O-beta-delta-galactopyranosyl-(1-4)- D-glucopyranose	HMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->8)-O-(N-acetyl-alpha-neuraminosyl)-(2->3)-O-beta-D-galactopyranosyl-(1->4)-D-glucopyranose	HMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->8)-O-(N-acetyl-alpha-neuraminosyl)-(2->3)-O-beta-delta-galactopyranosyl-(1->4)- D-glucopyranose	HMDB
O-(N-Acetyl-alpha-neuraminyl)-(2-8)-O-(N-acetyl-alpha-neuraminyl)-(2-3)-O-beta-D-galactopyranosyl-(1-4)-D-glucopyranose	HMDB
O-(N-Acetyl-alpha-neuraminyl)-(2-8)-O-(N-acetyl-alpha-neuraminyl)-(2-3)-O-beta-delta-galactopyranosyl-(1-4)-delta-glucopyranose	HMDB
O-(N-Acetyl-alpha-neuraminyl)-(2->8)-O-(N-acetyl-alpha-neuraminyl)-(2->3)-O-beta-D-galactopyranosyl-(1->4)-D-glucopyranose	HMDB
O-(N-Acetyl-alpha-neuraminyl)-(2->8)-O-(N-acetyl-alpha-neuraminyl)-(2->3)-O-beta-delta-galactopyranosyl-(1->4)-delta- glucopyranose	HMDB
Sia-(2-8)-sia-(2-3)gal-(1-4)GLC	HMDB
(2S,4S,5R,6R)-2-{[(1S,2R)-1-[(2R,3R,4S,6S)-6-carboxy-6-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}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]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate	Generator, HMDB
Disialyl lactose	MeSH, HMDB
AlphaNeu5ac(2,8)alphaneu5ac(2,3)betadgal(1,4)DGLC	MeSH, HMDB

Chemical Formula

C₃₄H₅₆N₂O₂₇

Average Molecular Weight

924.8056

Monoisotopic Molecular Weight

924.307044596

IUPAC Name

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

Traditional Name

CAS Registry Number

18409-15-9

SMILES

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

InChI Identifier

InChI=1S/C34H56N2O27/c1-9(41)35-17-11(43)3-33(31(53)54,61-26(17)19(46)13(45)5-37)60-15(7-39)21(48)27-18(36-10(2)42)12(44)4-34(62-27,32(55)56)63-28-20(47)14(6-38)58-30(24(28)51)59-25-16(8-40)57-29(52)23(50)22(25)49/h11-30,37-40,43-52H,3-8H2,1-2H3,(H,35,41)(H,36,42)(H,53,54)(H,55,56)/t11-,12-,13+,14+,15+,16+,17+,18+,19+,20-,21+,22+,23+,24+,25+,26+,27+,28-,29?,30-,33+,34-/m0/s1

InChI Key

IESOVNOGVZBLMG-MTEFBGAJSA-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
C-glucuronide
C-glycosyl compound
Glycosyl compound
O-glycosyl compound
Ketal
Dicarboxylic acid or derivatives
Pyran
Oxane
Acetamide
Carboxamide group
Hemiacetal
Secondary carboxylic acid amide
Secondary alcohol
Acetal
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Organopnictogen compound
Primary alcohol
Carbonyl group
Organonitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.5	ALOGPS
logP	-9.5	ChemAxon
logS	-0.95	ALOGPS
pKa (Strongest Acidic)	2.45	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	27	ChemAxon
Hydrogen Donor Count	18	ChemAxon
Polar Surface Area	480.63 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	188.88 m³·mol⁻¹	ChemAxon
Polarizability	86.15 Å³	ChemAxon
Number of Rings	4	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	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0cel-0828015098-b2d713e51be84bbf8263	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00mo-0209003000-1ce09f03167f95ceab80	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-6938001000-df20adf0314406572cbf	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0abc-2923810044-d28ff343a24de5edba71	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a70-8549110001-d97c4fa07291d27d2520	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-3559000000-43c7b65e0c738d84bc62	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05di-1311051209-8ba4b8dda3057cd245b8	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03l1-0491412612-76931820494134177702	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00pi-9870313140-5d37d73734c32dc83273	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-8090100084-7f9ba834399e650bd8eb	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-3090000020-6930c6437640788f5ca7	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9462010020-9d07f528035ec4ad7db1	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected and Quantified	2.163 - 7.569 uM		International Dai...	details

External Links

HMDB ID

HMDB0006692

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021805

KNApSAcK ID

Not Available

Chemspider ID

10174971

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12002504

PDB ID

Not Available

ChEBI ID

Not Available

References

Synthesis Reference

Stahl, Bernd; Boehm, Guenther; Finke, Berndt; Georgi, Gilda; Jelinek, Juergen; Schmitt, Joachim J. Oligosaccharide mixture. Ger. Offen. (2001), 6 pp. CODEN: GWXXBX DE 19958985 A1 20010613 CAN 135:18816 AN 2001:431764

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Paul McJarrow, Janneke van Amelsfort-Schoonbeek (2004). International Dairy Journal: Volume 14, Issue 7, July 2004, Pages 571-579. International Dairy Journal.

Showing metabocard for Disialyllactose (BMDB0006692)

Structure for BMDB0006692 (Disialyllactose)