Showing metabocard for Hyaluronan (BMDB0010366)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (20) Show 20 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:05:12 UTC
Update Date2020-04-22 15:40:24 UTC
BMDB IDBMDB0010366
Secondary Accession Numbers
  • BMDB10366
Metabolite Identification
Common NameHyaluronan
DescriptionHyaluronan belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group. Hyaluronan is a moderately basic compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
HyaluronateGenerator
HyaluronanHMDB
(2R,3R,4S,5S,6R)-4,5-Dihydroxy-3-{[(2R,3S,4R,5R,6S)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-4-methoxyoxan-2-yl]oxy}-6-methoxyoxane-2-carboxylateGenerator
Chemical FormulaC16H27NO12
Average Molecular Weight425.387
Monoisotopic Molecular Weight425.153325313
IUPAC Name(2R,3R,4S,5S,6R)-4,5-dihydroxy-3-{[(2R,3S,4R,5R,6S)-5-hydroxy-3-[(Z)-(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-4-methoxyoxan-2-yl]oxy}-6-methoxyoxane-2-carboxylic acid
Traditional Name(2R,3R,4S,5S,6R)-4,5-dihydroxy-3-{[(2R,3S,4R,5R,6S)-5-hydroxy-3-[(Z)-(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-4-methoxyoxan-2-yl]oxy}-6-methoxyoxane-2-carboxylic acid
CAS Registry Number9004-61-9
SMILES
CO[C@@H]1O[C@H]([C@H](O[C@H]2O[C@@H](CO)[C@H](O)[C@H](OC)[C@@H]2\N=C(\C)O)[C@@H](O)[C@@H]1O)C(O)=O
InChI Identifier
InChI=1S/C16H27NO12/c1-5(19)17-7-11(25-2)8(20)6(4-18)27-15(7)28-12-9(21)10(22)16(26-3)29-13(12)14(23)24/h6-13,15-16,18,20-22H,4H2,1-3H3,(H,17,19)(H,23,24)/t6-,7-,8-,9-,10-,11+,12+,13+,15+,16+/m0/s1
InChI KeyOHCSCOHNKUCRPF-QWWNONHYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentN-acyl-alpha-hexosamines
Alternative Parents
Substituents
  • Fatty acyl glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • N-acyl-alpha-hexosamine
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Fatty acyl
  • Pyran
  • Oxane
  • Secondary alcohol
  • Acetal
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organoheterocyclic compound
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Primary alcohol
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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-1.9ALOGPS
logP-2.6ChemAxon
logS-0.78ALOGPS
pKa (Strongest Acidic)3.44ChemAxon
pKa (Strongest Basic)1.32ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area196.96 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity89.33 m³·mol⁻¹ChemAxon
Polarizability39.99 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6u-0215900000-fa3f130d54c93e72a0e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-2975200000-b166b8b6a00dfa7b91c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-7933000000-86cebc7227c2b2f982e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05g0-3359600000-7ade34673fef30155596View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-4298200000-3d50612eb50fbafa0d52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9470000000-be5e833b2d72be3bbfa4View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0010366
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHyaluronic acid
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Hyaluronidase-2
General function:
Involved in hyalurononglucosaminidase activity
Specific function:
Hydrolyzes high molecular weight hyaluronic acid to produce an intermediate-sized product which is further hydrolyzed by sperm hyaluronidase to give small oligosaccharides. Displays very low levels of activity. Associates with and negatively regulates MST1R (By similarity).
Gene Name:
HYAL2
Uniprot ID:
Q8SQG8
Molecular weight:
53881.0
Enzyme Details
2. Hyaluronidase-1
General function:
Involved in hyalurononglucosaminidase activity
Specific function:
May have a role in promoting tumor progression. May block the TGFB1-enhanced cell growth (By similarity).
Gene Name:
HYAL1
Uniprot ID:
Q5E985
Molecular weight:
50508.0
Enzyme Details
3. Hyaluronan synthase 2
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Catalyzes the addition of GlcNAc or GlcUA monosaccharides to the nascent hyaluronan polymer. Therefore, it is essential to hyaluronan synthesis a major component of most extracellular matrices that has a structural role in tissues architectures and regulates cell adhesion, migration and differentiation. This is one of the isozymes catalyzing that reaction and it is particularly responsible for the synthesis of high molecular mass hyaluronan. Required for the transition of endocardial cushion cells into mesenchymal cells, a process crucial for heart development. May also play a role in vasculogenesis. High molecular mass hyaluronan also play a role in early contact inhibition a process which stops cell growth when cells come into contact with each other or the extracellular matrix (By similarity).
Gene Name:
HAS2
Uniprot ID:
O97711
Molecular weight:
63459.0
Enzyme Details
4. Brevican core protein
General function:
Involved in hyaluronic acid binding
Specific function:
May play a role in the terminally differentiating and the adult nervous system during postnatal development. Could stabilize interactions between hyaluronan (HA) and brain proteoglycans.
Gene Name:
BCAN
Uniprot ID:
Q28062
Molecular weight:
99554.0
Enzyme Details
5. Aggrecan core protein
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
This proteoglycan is a major component of extracellular matrix of cartilagenous tissues. A major function of this protein is to resist compression in cartilage. It binds avidly to hyaluronic acid via an N-terminal globular region. May play a regulatory role in the matrix assembly of the cartilage.
Gene Name:
ACAN
Uniprot ID:
P13608
Molecular weight:
246362.0
Enzyme Details
6. Versican core protein
General function:
Cell motility
Specific function:
May play a role in intercellular signaling and in connecting cells with the extracellular matrix. May take part in the regulation of cell motility, growth and differentiation. Binds hyaluronic acid.
Gene Name:
VCAN
Uniprot ID:
P81282
Molecular weight:
369990.0
Enzyme Details
7. Aggrecan
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q6XL67
Molecular weight:
246477.0
Enzyme Details
8. HAPLN3 protein
General function:
Involved in hyaluronic acid binding
Specific function:
Not Available
Gene Name:
HAPLN3
Uniprot ID:
A5PK97
Molecular weight:
41156.0
Enzyme Details
9. Hyaluronan and proteoglycan link protein 2
General function:
Involved in hyaluronic acid binding
Specific function:
Not Available
Gene Name:
HAPLN2
Uniprot ID:
Q0VD13
Molecular weight:
37910.0
Enzyme Details
10. Aggrecan
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q6XL68
Molecular weight:
220970.0
Enzyme Details
11. LYVE-1 protein
General function:
Involved in hyaluronic acid binding
Specific function:
Not Available
Gene Name:
LYVE-1
Uniprot ID:
A5D7P9
Molecular weight:
35561.0
Enzyme Details
12. Lymphatic vessel endothelial hyaluronic acid receptor 1
General function:
Involved in cell adhesion
Specific function:
Ligand-specific transporter trafficking between intracellular organelles (TGN) and the plasma membrane. Plays a role in autocrine regulation of cell growth mediated by growth regulators containing cell surface retention sequence binding (CRS). May act as a hyaluronan (HA) transporter, either mediating its uptake for catabolism within lymphatic endothelial cells themselves, or its transport into the lumen of afferent lymphatic vessels for subsequent re-uptake and degradation in lymph nodes.
Gene Name:
LYVE1
Uniprot ID:
Q6UC88
Molecular weight:
35561.0
Enzyme Details
13. Receptor for hyaluronic acid mediated motility
General function:
Involved in receptor activity
Specific function:
Not Available
Gene Name:
rhamm
Uniprot ID:
Q8SPM2
Molecular weight:
9452.0
Enzyme Details
14. TNF alpha induced protein 6
General function:
Involved in hyaluronic acid binding
Specific function:
Not Available
Gene Name:
TNFAIP6
Uniprot ID:
Q5W1C4
Molecular weight:
31425.0
Enzyme Details
15. CD44 antigen
General function:
Involved in hyaluronic acid binding
Specific function:
Not Available
Gene Name:
CD44
Uniprot ID:
Q0VD03
Molecular weight:
40087.0
Enzyme Details
16. Putative hyaluronan receptor for endocytosis
General function:
Involved in hyaluronic acid binding
Specific function:
Not Available
Gene Name:
hare
Uniprot ID:
Q864U4
Molecular weight:
54481.0
Enzyme Details
17. Hyaluronan binding protein 4
General function:
Not Available
Specific function:
Not Available
Gene Name:
HABP4
Uniprot ID:
A2VDN1
Molecular weight:
46017.0
Enzyme Details
18. Hyaluronan and proteoglycan link protein 1
General function:
Involved in hyaluronic acid binding
Specific function:
Stabilizes the aggregates of proteoglycan monomers with hyaluronic acid in the extracellular cartilage matrix.
Gene Name:
HAPLN1
Uniprot ID:
P55252
Molecular weight:
40288.0
Enzyme Details
19. CD44 antigen
General function:
Involved in hyaluronic acid binding
Specific function:
Cell-surface receptor that plays a role in cell-cell interactions, cell adhesion and migration, helping them to sense and respond to changes in the tissue microenvironment. Participates thereby in a wide variety of cellular functions including the activation, recirculation and homing of T-lymphocytes, hematopoiesis, inflammation and response to bacterial infection. Engages, through its ectodomain, extracellular matrix components such as hyaluronan/HA, collagen, growth factors, cytokines or proteases and serves as a platform for signal transduction by assembling, via its cytoplasmic domain, protein complexes containing receptor kinases and membrane proteases. Such effectors include PKN2, the RhoGTPases RAC1 and RHOA, Rho-kinases and phospholipase C that coordinate signaling pathways promoting calcium mobilization and actin-mediated cytoskeleton reorganization essential for cell migration and adhesion.
Gene Name:
CD44
Uniprot ID:
Q29423
Molecular weight:
40002.0
Enzyme Details
20. BCAN protein
General function:
Involved in hyaluronic acid binding
Specific function:
Not Available
Gene Name:
BCAN
Uniprot ID:
A4IF65
Molecular weight:
72137.0