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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-24 15:59:23 UTC
Update Date2021-09-14 15:18:07 UTC
HMDB IDHMDB0006588
Secondary Accession Numbers
  • HMDB06588
Metabolite Identification
Common NameDisialosyl galactosyl globoside
DescriptionDisialylgalactosylgloboside is a renal cell carcinoma (RCC)-associated antigen which mediates adhesion of RCC TOS-1 cells to certain lung tissue target cells. This adhesion process may initiate preferential lung metastasis of RCC (PMID: 10675485 ). Biosynthesis of disialylgalactosylgloboside (DSGG) is mediated by sialyltransferases from MSGG (monosialylgalactosylgloboside) (PMID: 17123352 ). Antidisialosyl antibodies have been found in some patients with chronic idiopathic ataxic neuropathy (CIAN) (PMID: 12420092 ). Globosides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Globosides are cerebrosides that contain additional carbohydrates, predominantly galactose, glucose or GalNAc. Lactosyl ceramide is a globoside found in erythrocyte plasma membranes. Globotriaosylceramide (also called ceramide trihexoside) contains glucose and two moles of galactose and accumulates, primarily in the kidneys, of patients suffering from Fabry disease.
Structure
Data?1582752393
Synonyms
ValueSource
DisialosylgalactosylglobosideHMDB
DSGGHMDB
Neuacalpha2-3galbeta1-3(neuacalpha2-6)galnacHMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->6)-O-[O-(N-acetyl-alpha-neuraminosyl)-(2->3)-beta-D-galactopyranosyl-(1->3)]-2-(acetylamino)-2-deoxy-D-galactoseHMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->6)-O-[O-(N-acetyl-alpha-neuraminosyl)-(2->3)-beta-delta-galactopyranosyl-(1->3)]-2-(acetylamino)-2-deoxy-delta-galactoseHMDB
DisialylgalactosylglobosideMeSH, HMDB
(2R,4S,5R,6R)-2-{[(2R,3S,4R,5R)-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}-2,3-dihydroxy-5-[(1-hydroxyethylidene)amino]-6-oxohexyl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylateGenerator, HMDB
Disialosyl galactosyl globosideMeSH
Chemical FormulaC36H59N3O27
Average Molecular Weight965.8576
Monoisotopic Molecular Weight965.333593697
IUPAC Name(2R,4S,5R,6R)-2-{[(2R,3S,4R,5R)-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}-5-acetamido-2,3-dihydroxy-6-oxohexyl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Traditional Name(2R,4S,5R,6R)-2-{[(2R,3S,4R,5R)-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}-5-acetamido-2,3-dihydroxy-6-oxohexyl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
CAS Registry Number71764-07-3
SMILES
[H][C@]1(O[C@@](C[C@H](O)[C@H]1NC(C)=O)(OC[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O[C@@]2(C[C@H](O)[C@@H](NC(C)=O)[C@@]([H])(O2)[C@H](O)[C@H](O)CO)C(O)=O)[C@H]1O)[C@@H](NC(C)=O)C=O)C(O)=O)[C@H](O)[C@H](O)CO
InChI Identifier
InChI=1S/C36H59N3O27/c1-11(44)37-14(6-40)28(25(54)19(51)10-61-35(33(57)58)4-15(47)21(38-12(2)45)29(64-35)23(52)17(49)7-41)63-32-27(56)31(26(55)20(9-43)62-32)66-36(34(59)60)5-16(48)22(39-13(3)46)30(65-36)24(53)18(50)8-42/h6,14-32,41-43,47-56H,4-5,7-10H2,1-3H3,(H,37,44)(H,38,45)(H,39,46)(H,57,58)(H,59,60)/t14-,15-,16-,17+,18+,19+,20+,21+,22+,23+,24+,25-,26-,27+,28+,29+,30+,31-,32-,35+,36-/m0/s1
InChI KeySKJCZIMWAATHMG-CZYIXMLQSA-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
  • N-acylneuraminic acid
  • Neuraminic acid
  • Fatty acyl glycoside of mono- or disaccharide
  • Fatty acyl glycoside
  • C-glucuronide
  • Alkyl glycoside
  • C-glycosyl compound
  • O-glycosyl compound
  • Glycosyl compound
  • Ketal
  • Amino saccharide
  • Pyran
  • Dicarboxylic acid or derivatives
  • Oxane
  • Monosaccharide
  • Fatty acyl
  • Acetamide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Aldehyde
  • Organic nitrogen compound
  • Primary alcohol
  • Organopnictogen compound
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility34.4 g/LALOGPS
logP10(-2.5) g/LALOGPS
logP10(-10) g/LChemAxon
logS10(-1.4) g/LALOGPS
pKa (Strongest Acidic)2.6ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count27ChemAxon
Hydrogen Donor Count18ChemAxon
Polar Surface Area497.34 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity201.4 m³·mol⁻¹ChemAxon
Polarizability90.53 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disialosyl galactosyl globoside 10V, Positive-QTOFsplash10-052b-0000213009-b5afc95a9679009dfda22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disialosyl galactosyl globoside 20V, Positive-QTOFsplash10-0a59-2114119001-63997878e38b8b3b3d012017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disialosyl galactosyl globoside 40V, Positive-QTOFsplash10-03di-7189436001-dfe5ac83e6e05b29f69f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disialosyl galactosyl globoside 10V, Negative-QTOFsplash10-059w-1611010109-d42a43930e46c88385312017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disialosyl galactosyl globoside 20V, Negative-QTOFsplash10-0a4i-6549111113-2e571a92e098b86503552017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disialosyl galactosyl globoside 40V, Negative-QTOFsplash10-0a4i-7359121100-6c9aa0b6e112328fd50c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disialosyl galactosyl globoside 10V, Positive-QTOFsplash10-014i-0000112009-acd1278d76e2cc2fd17a2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disialosyl galactosyl globoside 20V, Positive-QTOFsplash10-0fmj-2551905328-68cf4bab4557987c3d4a2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disialosyl galactosyl globoside 40V, Positive-QTOFsplash10-069r-9630400122-5157de188ab207e611992021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disialosyl galactosyl globoside 10V, Negative-QTOFsplash10-08mr-9051000045-d1d82c4a04bb936939322021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disialosyl galactosyl globoside 20V, Negative-QTOFsplash10-053r-5090000053-10f39d35d81f67abec312021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disialosyl galactosyl globoside 40V, Negative-QTOFsplash10-0pdi-8791211231-90f6bc39ee21fec166462021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023988
KNApSAcK IDNot Available
Chemspider ID112280
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound126334
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Senda M, Ito A, Tsuchida A, Hagiwara T, Kaneda T, Nakamura Y, Kasama K, Kiso M, Yoshikawa K, Katagiri Y, Ono Y, Ogiso M, Urano T, Furukawa K, Oshima S, Furukawa K: Identification and expression of a sialyltransferase responsible for the synthesis of disialylgalactosylgloboside in normal and malignant kidney cells: downregulation of ST6GalNAc VI in renal cancers. Biochem J. 2007 Mar 15;402(3):459-70. [PubMed:17123352 ]
  2. Satoh M, Nejad FM, Ohtani H, Ito A, Ohyama C, Saito S, Orikasa S, Hakomori S: Association of renal cell carcinoma antigen, disialylgalactosylgloboside, with c-Src and Rho A in clustered domains at the surface membrane. Int J Oncol. 2000 Mar;16(3):529-36. [PubMed:10675485 ]
  3. Serrano-Munuera C, Rojas-Garcia R, Gallardo E, De Luna N, Buenaventura I, Ferrero M, Garcia T, Garcia-Merino JA, Gonzalez-Rodriguez C, Guerriero A, Marco M, Marquez C, Grau JM, Graus F, Illa I: Antidisialosyl antibodies in chronic idiopathic ataxic neuropathy. J Neurol. 2002 Nov;249(11):1525-8. [PubMed:12420092 ]

Enzymes

General function:
Involved in sialyltransferase activity
Specific function:
Alpha-2,6-sialyltransferase involved in the synthesis of alpha-series gangliosides. Has activity toward GD1a, GT1b and GM1b. Has no activity toward glycoproteins. Responsible for the biosynthesis of DSGG (disialylgalactosylgloboside) from MSGG (monosialylgalactosylgloboside) in normal and malignant kidney. Participates in the synthesis of disialyl Lewis a (Le(a)), a representative tumor-associated antigen in cancers of the pancreas and colon, in colon tissues
Gene Name:
ST6GALNAC6
Uniprot ID:
Q969X2
Molecular weight:
38067.3