Showing metabocard for 3'-Sialyllactose (BMDB0000825)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:37:09 UTC
Update Date2020-06-04 20:51:06 UTC
BMDB IDBMDB0000825
Secondary Accession Numbers
  • BMDB00825
Metabolite Identification
Common Name3'-Sialyllactose
Description3'-Sialyllactose belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent. Based on a literature review a significant number of articles have been published on 3'-Sialyllactose.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2>3')-a-sialyllactoseHMDB
(2>3')-alpha-sialyllactoseHMDB
3'-(N-Acetyl-a-neuraminosyl)lactoseHMDB
3'-(N-Acetyl-alpha-neuraminosyl)lactoseHMDB
3'-a-SialyllactoseHMDB
3'-alpha-SialyllactoseHMDB
3'-MonosialyllactoseHMDB
3'-N-Acetylneuraminyl-D-lactoseHMDB
3'-N-Acetylneuraminyl-delta-lactoseHMDB
3'-Sialyl-D-lactoseHMDB
3'-Sialyl-delta-lactoseHMDB
32-N-Acetyl-a-neuraminyllactoseHMDB
32-N-Acetyl-alpha-neuraminyllactoseHMDB
a-Neu5ac-(2>3)-b-D-gal-(1>4)-D-GLCHMDB
a2,3-SialyllactoseHMDB
alpha-Neu5ac-(2>3)-beta-D-gal-(1>4)-D-GLCHMDB
alpha-Neu5ac-(2>3)-beta-delta-gal-(1>4)-delta-GLCHMDB
N-AcetylneuraminoyllactoseHMDB
N-Acetylneuraminyl-2-3-galactopyranosyl-1-4-glucopyranoseHMDB
(2S,4S,5R,6R)-2-{[(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]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylateHMDB
3'-SialyllactoseMeSH
Chemical FormulaC23H39NO19
Average Molecular Weight633.5511
Monoisotopic Molecular Weight633.211628071
IUPAC Name(2S,4S,5R,6R)-2-{[(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-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Traditional Name(2S,4S,5R,6R)-2-{[(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-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
CAS Registry Number35890-38-1
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]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)[C@@H]1O)C(O)=O)[C@H](O)[C@H](O)CO
InChI Identifier
InChI=1S/C23H39NO19/c1-7(29)24-13-8(30)2-23(22(38)39,42-19(13)15(35)10(32)4-26)43-20-16(36)12(6-28)40-21(17(20)37)41-18(11(33)5-27)14(34)9(31)3-25/h3,8-21,26-28,30-37H,2,4-6H2,1H3,(H,24,29)(H,38,39)/t8-,9-,10+,11+,12+,13+,14+,15+,16-,17+,18+,19+,20-,21-,23-/m0/s1
InChI KeyOIZGSVFYNBZVIK-FHHHURIISA-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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentN-acylneuraminic acids
Alternative Parents
Substituents
  • Oligosaccharide
  • N-acylneuraminic acid
  • Neuraminic acid
  • Fatty acyl glycoside
  • C-glucuronide
  • Alkyl glycoside
  • C-glycosyl compound
  • O-glycosyl compound
  • Glycosyl compound
  • Ketal
  • Beta-hydroxy aldehyde
  • Fatty acyl
  • Oxane
  • Pyran
  • Acetamide
  • Alpha-hydroxyaldehyde
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Polyol
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Aldehyde
  • Organic nitrogen compound
  • Primary alcohol
  • Organopnictogen compound
  • Organic oxide
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.6ALOGPS
logP-7.7ChemAxon
logS-0.85ALOGPS
pKa (Strongest Acidic)2.84ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area342.92 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity130.03 m³·mol⁻¹ChemAxon
Polarizability58.66 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0329-9200136000-fffce6abd054ee490a92View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_10) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_11) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_12) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_13) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_14) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-0091000000-7e22772e5e2744079301View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0229-0390000000-002eec5ec089f1eb0e5bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00xs-1930000000-89aed3dbc59d2c137408View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02u1-1905068000-8188f1508e1a6fe4b08aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0059-1619000000-56b3f7f1b9406974b2ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03e9-8953000000-14875e5817ba52578c18View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0229-5910085000-1d9e7dc1c1b15e596033View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a73-9647001000-3efe2b78863a5580b526View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9843000000-ba45a1d17f709c61e7b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2120279000-b879570d20ee857cbdc0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08gl-2010291000-4d99393826350dc02114View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9110000000-cc64071c39126f0d8560View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0frb-1400894000-dfbfe52cc93f55bebc01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0irr-9414852000-d2182ab82f00048d4b3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-024l-9614210000-0ef934abaed3d29bcc58View in MoNA
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Colostrum
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
ColostrumDetected and Quantified150 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified1131.716 +/- 42.617 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified55.244 - 78.920 uMNot SpecifiedNot Specified
Normal
    • International Dai...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000825
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021795
KNApSAcK IDNot Available
Chemspider ID110445
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5788
PubChem Compound123914
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceMasuda, Mika; Kawase, Yuuji; Kawase, Mitsuo. Enzymic synthesis of (a2-3) sialyllactose using a membrane reactor. Seibutsu Kogaku Kaishi (2001), 79(9), 345-348.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Nakamura T, Kawase H, Kimura K, Watanabe Y, Ohtani M, Arai I, Urashima T: Concentrations of sialyloligosaccharides in bovine colostrum and milk during the prepartum and early lactation. J Dairy Sci. 2003 Apr;86(4):1315-20. doi: 10.3168/jds.S0022-0302(03)73715-1. [PubMed:12741556 ]
  2. Paul McJarrow, Janneke van Amelsfort-Schoonbeek (2004). International Dairy Journal: Volume 14, Issue 7, July 2004, Pages 571-579. International Dairy Journal.