Showing metabocard for Hyaluronic acid (BMDB0002061)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (16) Show 16 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:50:35 UTC
Update Date2020-04-22 15:09:36 UTC
BMDB IDBMDB0002061
Secondary Accession Numbers
  • BMDB02061
Metabolite Identification
Common NameHyaluronic acid
DescriptionHyaluronic acid, also known as hyaluronate, 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. Hyaluronic acid is a moderately basic compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
HyaluronateGenerator
(2S,3S,4R,5R,6S)-4,5-Dihydroxy-6-{[(2R,3S,4R,5R,6R)-3-hydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxy}-3-methoxyoxane-2-carboxylateGenerator
Chemical FormulaC16H27NO12
Average Molecular Weight425.387
Monoisotopic Molecular Weight425.153325313
IUPAC Name(2S,3S,4R,5R,6S)-4,5-dihydroxy-6-{[(2R,3S,4R,5R,6R)-3-hydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxy}-3-methoxyoxane-2-carboxylic acid
Traditional Namehyaluronate
CAS Registry NumberNot Available
SMILES
[H][C@]1(CO)O[C@@]([H])(OC)[C@]([H])(N=C(C)O)[C@@]([H])(O[C@@]2([H])O[C@]([H])(C(O)=O)[C@@]([H])(OC)[C@]([H])(O)[C@@]2([H])O)[C@]1([H])O
InChI Identifier
InChI=1S/C16H27NO12/c1-5(19)17-7-11(8(20)6(4-18)27-15(7)26-3)28-16-10(22)9(21)12(25-2)13(29-16)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+/m1/s1
InChI KeyOEANUJAFZLQYOD-RFLIHGOWSA-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
  • N-acyl-alpha-hexosamine
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Oxane
  • Pyran
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Primary alcohol
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Lysosome
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-2.7ChemAxon
logS-0.76ALOGPS
pKa (Strongest Acidic)3.14ChemAxon
pKa (Strongest Basic)1.31ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area196.96 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity89.33 m³·mol⁻¹ChemAxon
Polarizability39.4 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, Positivesplash10-05pc-0194700000-fe6f4bd1bb166e48c0bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014u-0491000000-0976e3d7c3960a6a50d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-5690000000-5e11eb0ed1b61a8ca95bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05gi-3649700000-99dd5c6de8d610c9f187View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06sl-4496200000-ce3029a76a103bb6de93View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9300000000-97898344d6cb9083991cView in MoNA
Biological Properties
Cellular Locations
  • Lysosome
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDNot Available
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 Compound57504018
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceTan, Wensong; Hu, Yihong; Zhang, Xu; Cai, Haibo. Method for preparing hyaluronic acid from microbial fermentation broth. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 10pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. 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
2. 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
3. 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
4. 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
5. 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
6. 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
7. 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
8. 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
9. 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
10. 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
11. 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
12. 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
13. 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
14. 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
15. 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
16. BCAN protein
General function:
Involved in hyaluronic acid binding
Specific function:
Not Available
Gene Name:
BCAN
Uniprot ID:
A4IF65
Molecular weight:
72137.0