Showing Compound Disialyllacto-N-fucopentaose II (FDB024022)

Record Information

Version

1.0

Creation date

2011-09-21 00:38:39 UTC

Update date

2015-07-21 06:57:58 UTC

Primary ID

FDB024022

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Disialyllacto-N-fucopentaose II

Description

Disialyllacto-N-fucopentaose II is a sialylated oligosaccharide of human milk. Neutral milk oligosaccharides vary among individuals and over the course of lactation. Sialylated oligosaccharides are important components of glycoproteins and glycolipids and also occur as free oligosaccharides in several body fluids. In human milk, both free and bound sialylated oligosaccharides have potential biological activity and are known to inhibit viral infection. (PMID: 10683228, 1778981, 2327786) [HMDB]

CAS Number

127783-55-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(2R,4S,5R,6R)-2-{[(2R,3S,4R,5R,6S)-4-{[(2R,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}-6-{[(2R,3S,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-[(1-hydroxyethylidene)amino]-3-{[(2S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]methoxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate	Generator, HMDB
D-Glucose, O-(N-acetyl-a-neuraminosyl)-(2->3)-O-b-D-galactopyranosyl-(1->3)]-O-[6-deoxy-a-L-galactopyranosyl-(1->4)-O-[N-acetyl-a-neuraminosyl-(2->6)]-O-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1->3)-O-b-D-galactopyranosyl-(1->4)-	manual
DSLNFP-II	HMDB
Neu5aca2-3galb1-3GLCN(neu5aca2-6)(fuca1-4)acb1-3galb1-4GLC	HMDB
Neu5aca2-3galb1-3glcn(neu5aca2-6)(fuca1-4)acb1-3galb1-4glc	HMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->6)-O-[O-(N-acetyl-alpha-neuraminosyl)-(2->3)-beta-D-galactopyranosyl-(1->3)]-O-[6-deoxy-alpha-L-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-[O-(N-acetyl-alpha-neuraminosyl)-(2->3)-beta-delta-galactopyranosyl-(1->3)]-O-[6-deoxy-alpha-L-galactopyranosyl-(1->4)]-O-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->3)-O-beta-delta-galactopyranosyl-(1->4)- D-glucose	HMDB

Showing 1 to 7 of 7 entries

Predicted Properties

Property	Value	Source
Water Solubility	167 g/L	ALOGPS
logP	-2	ALOGPS
logP	-15	ChemAxon
logS	-0.93	ALOGPS
pKa (Strongest Acidic)	2.52	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	41	ChemAxon
Hydrogen Donor Count	26	ChemAxon
Polar Surface Area	714.56 Å²	ChemAxon
Rotatable Bond Count	31	ChemAxon
Refractivity	297.1 m³·mol⁻¹	ChemAxon
Polarizability	135.76 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C54H89N3O41

IUPAC name

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

InChI Identifier

InChI=1S/C54H89N3O41/c1-14-30(73)36(79)37(80)48(88-14)93-41-26(13-87-53(51(83)84)5-18(67)27(55-15(2)64)42(96-53)32(75)21(70)8-59)91-47(95-45-34(77)24(11-62)89-49(38(45)81)92-40(23(72)10-61)31(74)20(69)7-58)29(57-17(4)66)44(41)94-50-39(82)46(35(78)25(12-63)90-50)98-54(52(85)86)6-19(68)28(56-16(3)65)43(97-54)33(76)22(71)9-60/h7,14,18-50,59-63,67-82H,5-6,8-13H2,1-4H3,(H,55,64)(H,56,65)(H,57,66)(H,83,84)(H,85,86)/t14-,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-,53+,54-/m0/s1

InChI Key

KNWXPODBRXAWBX-PFNBIPCHSA-N

Isomeric SMILES

[H][C@]1(O[C@@](C[C@H](O)[C@H]1NC(C)=O)(OC[C@H]1O[C@@H](OC2[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]2O)[C@H](NC(C)=O)[C@@H](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](O)CO)C(O)=O)[C@H]2O)[C@@H]1O[C@@H]1O[C@@H](C)[C@@H](O)[C@@H](O)C1O)C(O)=O)[C@H](O)[C@H](O)CO

Average Molecular Weight

1436.28

Monoisotopic Molecular Weight

1435.497149365

Classification

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
Dicarboxylic acid or derivatives
Fatty acyl
Pyran
Oxane
Acetamide
Alpha-hydroxyaldehyde
Carboxamide group
Secondary alcohol
Secondary carboxylic acid amide
Polyol
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Acetal
Organoheterocyclic compound
Primary alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Aldehyde
Organic nitrogen compound
Organopnictogen compound
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Source:

Endogenous

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0852900004-fb051fc2e5b00c6d7774	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004j-0901000023-954fbc63fc5f17424c27	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01qi-4923000043-add0b6329b307308c6ff	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00xr-2429600000-d9b1abae14c92eaecc89	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0aor-5349400000-4ba5bd4eba2005923469	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-7946500001-46c21249bcbeb3e1e538	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-2078900000-1f70706f7fd879493376	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01q9-1039200000-190e0674cce6de1eb7b9	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9142100000-b3bdaf55dba3b3204b11	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0i09-4842900001-d24ee3dcb30ce8b0af23	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9840200000-981735be69e941a22f65	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01p2-4923500001-16080f4d506ba850bfed	2021-09-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

17216400

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

22833676

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB06676

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Disialyllacto-N-fucopentaose II (FDB024022)

Structure for FDB024022 (Disialyllacto-N-fucopentaose II)