Lacto-N-decaose (CHEM036186)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:18:02 UTC
Update Date2016-11-09 01:21:27 UTC
Accession NumberCHEM036186
Identification
Common NameLacto-N-decaose
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Galb1-4glcnacb1-6(galb1-3galnacb1-3)galb1-4glcnacb1-6(galb1-3glcnacb1-3)galb1-4GLCHMDB
N-[(3R,5S,6R)-6-Ethyl-4-{[(3R,4S,5R,6R)-6-ethyl-3,4,5-trimethyloxan-2-yl]oxy}-2-{[(3R,5R)-2-({[(3R,4R,6R)-6-ethyl-5-{[(3R,5R,6S)-4-{[(3R,5S,6R)-6-ethyl-4-{[(3R,4S,5R,6R)-6-ethyl-3,4,5-trimethyloxan-2-yl]oxy}-3-[(1-hydroxyethylidene)amino]-5-methyloxan-2-yl]oxy}-6-({[(3R,4R,6R)-6-ethyl-5-{[(3R,4S,5R,6R)-6-ethyl-3,4,5-trimethyloxan-2-yl]oxy}-3-[(1-hydroxyethylidene)amino]-4-methyloxan-2-yl]oxy}methyl)-3,5-dimethyloxan-2-yl]oxy}-3-[(1-hydroxyethylidene)amino]-4-methyloxan-2-yl]oxy}methyl)-3,5-dimethyl-6-{[(2R,4R,5R)-2,4,5,6-tetramethyloxan-3-yl]oxy}oxan-4-yl]oxy}-5-methyloxan-3-yl]ethanimidateGenerator, HMDB
Chemical FormulaC95H168N4O23
Average Molecular Mass1734.363 g/mol
Monoisotopic Mass1733.210 g/mol
CAS Registry Number87003-65-4
IUPAC NameN-[(3R,4R,6R)-2-{[(2S,3R,5R)-4-{[(3R,5S,6R)-3-acetamido-6-ethyl-4-{[(3R,4S,5R,6R)-6-ethyl-3,4,5-trimethyloxan-2-yl]oxy}-5-methyloxan-2-yl]oxy}-6-{[(2R,4R,5R)-5-acetamido-6-{[(3R,5R)-4-{[(3R,5S,6R)-3-acetamido-6-ethyl-4-{[(3R,4S,5R,6R)-6-ethyl-3,4,5-trimethyloxan-2-yl]oxy}-5-methyloxan-2-yl]oxy}-3,5-dimethyl-6-{[(2R,4R,5R)-2,4,5,6-tetramethyloxan-3-yl]oxy}oxan-2-yl]methoxy}-2-ethyl-4-methyloxan-3-yl]oxy}-3,5-dimethyloxan-2-yl]methoxy}-6-ethyl-5-{[(3R,4S,5R,6R)-6-ethyl-3,4,5-trimethyloxan-2-yl]oxy}-4-methyloxan-3-yl]acetamide
Traditional NameN-[(3R,4R,6R)-2-{[(2S,3R,5R)-4-{[(3R,5S,6R)-3-acetamido-6-ethyl-4-{[(3R,4S,5R,6R)-6-ethyl-3,4,5-trimethyloxan-2-yl]oxy}-5-methyloxan-2-yl]oxy}-6-{[(2R,4R,5R)-5-acetamido-6-{[(3R,5R)-4-{[(3R,5S,6R)-3-acetamido-6-ethyl-4-{[(3R,4S,5R,6R)-6-ethyl-3,4,5-trimethyloxan-2-yl]oxy}-5-methyloxan-2-yl]oxy}-3,5-dimethyl-6-{[(2R,4R,5R)-2,4,5,6-tetramethyloxan-3-yl]oxy}oxan-2-yl]methoxy}-2-ethyl-4-methyloxan-3-yl]oxy}-3,5-dimethyloxan-2-yl]methoxy}-6-ethyl-5-{[(3R,4S,5R,6R)-6-ethyl-3,4,5-trimethyloxan-2-yl]oxy}-4-methyloxan-3-yl]acetamide
SMILESCC[C@H]1OC(OC2[C@H](C)[C@@H](NC(C)=O)C(OC[C@H]3OC(OC4[C@H](C)[C@@H](NC(C)=O)C(OCC5OC(OC6[C@@H](C)OC(C)[C@H](C)[C@H]6C)[C@H](C)C(OC6O[C@H](CC)[C@H](C)C(OC7O[C@H](CC)[C@H](C)[C@H](C)[C@H]7C)[C@H]6NC(C)=O)[C@H]5C)O[C@@H]4CC)[C@H](C)C(OC4O[C@H](CC)[C@H](C)C(OC5O[C@H](CC)[C@H](C)[C@H](C)[C@H]5C)[C@H]4NC(C)=O)[C@H]3C)O[C@@H]2CC)[C@H](C)[C@@H](C)[C@H]1C
InChI IdentifierInChI=1S/C95H168N4O23/c1-33-67-46(12)42(8)50(16)87(107-67)119-83-57(23)76(96-63(29)100)92(112-72(83)38-6)105-41-75-56(22)81(117-95-79(99-66(32)103)86(54(20)71(37-5)111-95)122-89-52(18)44(10)48(14)69(35-3)109-89)60(26)91(115-75)120-84-58(24)77(97-64(30)101)93(113-73(84)39-7)104-40-74-55(21)80(59(25)90(114-74)118-82-49(15)45(11)61(27)106-62(82)28)116-94-78(98-65(31)102)85(53(19)70(36-4)110-94)121-88-51(17)43(9)47(13)68(34-2)108-88/h42-62,67-95H,33-41H2,1-32H3,(H,96,100)(H,97,101)(H,98,102)(H,99,103)/t42-,43-,44-,45+,46+,47+,48+,49+,50+,51+,52+,53-,54-,55-,56-,57+,58+,59+,60+,61?,62+,67+,68+,69+,70+,71+,72+,73+,74?,75+,76+,77+,78+,79+,80?,81?,82?,83?,84?,85?,86?,87?,88?,89?,90?,91?,92?,93?,94?,95?/m0/s1
InChI KeySJQVFWDWZSSQJI-RIIJGTCGSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharides
Alternative Parents
Substituents
  • Monosaccharide
  • Oxane
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Acetal
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.003 g/LALOGPS
logP6.45ALOGPS
logP16.37ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)12.22ChemAxon
pKa (Strongest Basic)0.063ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count23ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area291.77 ŲChemAxon
Rotatable Bond Count31ChemAxon
Refractivity456.74 m³·mol⁻¹ChemAxon
Polarizability200.68 ųChemAxon
Number of Rings10ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-4408089120-9c1aa6124c4d66a69862Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06rx-8339035210-97265c47a0356ad4740dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-057u-9200022010-4491299716214b1b22b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01r6-2209075200-43456e8a2b39cb07bc13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0300-0434497400-a5461effe194dcf883e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-2903401200-ed99538b03b8df1c6c63Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0089-1603010900-0b727372a596779a88c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0102223900-71a75a4248ed6ae25b12Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001m-2706439710-67b2cd35d4694a39e6e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0200144900-fe91aca74e071250eb82Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00uu-3900112500-7a934b8546e21a6900abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001l-6912520200-22880362940beb2c35e7Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0006650
FooDB IDFDB024018
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID21427281
ChEBI IDNot Available
PubChem Compound ID53477880
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Chai W, Piskarev VE, Zhang Y, Lawson AM, Kogelberg H: Structural determination of novel lacto-N-decaose and its monofucosylated analogue from human milk by electrospray tandem mass spectrometry and 1H NMR spectroscopy. Arch Biochem Biophys. 2005 Feb 1;434(1):116-27.
2. Coppa GV, Pierani P, Zampini L, Bruni S, Carloni I, Gabrielli O: Characterization of oligosaccharides in milk and feces of breast-fed infants by high-performance anion-exchange chromatography. Adv Exp Med Biol. 2001;501:307-14.
3. Von Seggern CE, Cotter RJ: Fragmentation studies of noncovalent sugar-sugar complexes by infrared atmospheric pressure MALDI. J Am Soc Mass Spectrom. 2003 Oct;14(10):1158-65.
4. Ninonuevo MR, Park Y, Yin H, Zhang J, Ward RE, Clowers BH, German JB, Freeman SL, Killeen K, Grimm R, Lebrilla CB: A strategy for annotating the human milk glycome. J Agric Food Chem. 2006 Oct 4;54(20):7471-80.