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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-06-07 00:22:47 UTC
HMDB IDHMDB0000693
Secondary Accession Numbers
  • HMDB00693
Metabolite Identification
Common NameHeparan sulfate
DescriptionHeparan sulfate is a heteropolysaccharide that is similar in structure to heparin. It accumulates in individuals with mucopolysaccharidosis. Heparan sulfate (HS) is a linear polysaccharide found in all animal tissues. It occurs as a proteoglycan (PG) in which two or three HS chains are attached in close proximity to cell suface or extracellular matrix proteins.[1][2] It is in this form that HS binds to a variety of protein ligands and regulates a wide variety of biological activities, including developmental processes, angiogenesis, blood coagulation and tumour metastasis. (Wikipedia).
Structure
Thumb
Synonyms
ValueSource
Heparan sulfuric acidGenerator
Heparan sulphateGenerator
Heparan sulphuric acidGenerator
alpha-IdosaneHMDB
Heparan N-sulfateHMDB
Heparan N-sulphateHMDB
Heparatan sulfateHMDB
Heparatan sulphateHMDB
HeparitinHMDB
Heparitin monosulfateHMDB
Heparitin monosulphateHMDB
Heparitin sulfateHMDB
Heparitin sulphateHMDB
HHS 5HMDB
N-Acetylheparan sulfateHMDB
N-Acetylheparan sulphateHMDB
SuleparoidHMDB
TavidanHMDB
Chemical FormulaC14H25NO21S3
Average Molecular Weight639.52
Monoisotopic Molecular Weight639.008120351
IUPAC Name(2S,3R,4R,5S,6R)-4-hydroxy-6-{[(2S,3R,4S,5S,6R)-4-hydroxy-6-methoxy-5-[(sulfooxy)amino]-2-[(sulfooxy)methyl]oxan-3-yl]oxy}-3-methoxy-5-(sulfooxy)oxane-2-carboxylic acid
Traditional Name(2S,3R,4R,5S,6R)-4-hydroxy-6-{[(2S,3R,4S,5S,6R)-4-hydroxy-6-methoxy-5-[(sulfooxy)amino]-2-[(sulfooxy)methyl]oxan-3-yl]oxy}-3-methoxy-5-(sulfooxy)oxane-2-carboxylic acid
CAS Registry Number9050-30-0
SMILES
CO[C@@H]1O[C@@H](COS(O)(=O)=O)[C@H](O[C@@H]2O[C@@H]([C@H](OC)[C@@H](O)[C@@H]2OS(O)(=O)=O)C(O)=O)[C@@H](O)[C@@H]1NOS(O)(=O)=O
InChI Identifier
InChI=1S/C14H25NO21S3/c1-29-9-7(17)10(35-38(23,24)25)14(34-11(9)12(18)19)33-8-4(3-31-37(20,21)22)32-13(30-2)5(6(8)16)15-36-39(26,27)28/h4-11,13-17H,3H2,1-2H3,(H,18,19)(H,20,21,22)(H,23,24,25)(H,26,27,28)/t4-,5-,6-,7+,8-,9+,10-,11-,13+,14+/m0/s1
InChI KeyAUQASCCBXZRMEG-RHKLHVFKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as disaccharide sulfates. These are disaccharides carrying one or more sulfate group on a sugar unit.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentDisaccharide sulfates
Alternative Parents
Substituents
  • Disaccharide sulfate
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Glycosyl compound
  • O-glycosyl compound
  • Sulfuric acid ester
  • Alkyl sulfate
  • Sulfate-ester
  • Sulfuric acid monoester
  • Pyran
  • Oxane
  • Organic sulfuric acid or derivatives
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

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-2.2ALOGPS
logP-8.1ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)-3.3ChemAxon
pKa (Strongest Basic)1.99ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area326.74 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity121.6 m³·mol⁻¹ChemAxon
Polarizability52.51 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0kai-9400000000-404fa85a4342eafffaecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9400000000-eec3b32ccab8e708c47bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9400000000-ad221bda41e892ec4944View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue Locations
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Muscle
  • Nerve Cells
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Skeletal Muscle
  • Spleen
  • Testes
  • Uterus
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.5 (0.0-1.0) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.6 (1.4-6.1) uMAdult (>18 years old)BothLiver disease with gastrointestinal bleeding details
Associated Disorders and Diseases
Disease References
Liver disease
  1. McKee RF, Hodson S, Dawes J, Garden OJ, Carter DC: Plasma concentrations of endogenous heparinoids in portal hypertension. Gut. 1992 Nov;33(11):1549-52. [PubMed:1452082 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022184
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC00925
BioCyc IDCPD-7177
BiGG IDNot Available
Wikipedia LinkHeparan sulfate
METLIN IDNot Available
PubChem Compound53477715
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceMeier, Bernd Horst; Meier, Nele. Manufacture and use of modified adducts of polysaccharides and chitosan or chitin and a process to improve the preparation of polysaccharide-drug conjugates. PCT Int. Appl. (2007), 67pp. CODEN: PIXXD2 WO 2007122269 A1 20071101 CAN 147:487869 AN 2007:1237349
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Dempsey LA, Plummer TB, Coombes SL, Platt JL: Heparanase expression in invasive trophoblasts and acute vascular damage. Glycobiology. 2000 May;10(5):467-75. [PubMed:10764835 ]
  2. Wasserman L, Abramovici A, Shlesinger H, Goldman JA, Allalouf D: Histochemical localization of acidic glycosaminoglycans in normal human placentae. Placenta. 1983 Jan-Apr;4(1):101-8. [PubMed:6406996 ]
  3. Inoue H, Otsu K, Yoneda M, Kimata K, Suzuki S, Nakanishi Y: Glycosaminoglycan sulfotransferases in human and animal sera. J Biol Chem. 1986 Apr 5;261(10):4460-9. [PubMed:3457007 ]
  4. Nader HB, Lopes CC, Rocha HA, Santos EA, Dietrich CP: Heparins and heparinoids: occurrence, structure and mechanism of antithrombotic and hemorrhagic activities. Curr Pharm Des. 2004;10(9):951-66. [PubMed:15078126 ]
  5. Henriquez JP, Casar JC, Fuentealba L, Carey DJ, Brandan E: Extracellular matrix histone H1 binds to perlecan, is present in regenerating skeletal muscle and stimulates myoblast proliferation. J Cell Sci. 2002 May 15;115(Pt 10):2041-51. [PubMed:11973346 ]
  6. Hjelm Cluff A, Malmstrom A, Tingaker B, David G, Ekman-Ordeberg G: Normal labor associated with changes in uterine heparan sulfate proteoglycan expression and localization. Acta Obstet Gynecol Scand. 2005 Mar;84(3):217-24. [PubMed:15715528 ]
  7. Yu WH, Yu S, Meng Q, Brew K, Woessner JF Jr: TIMP-3 binds to sulfated glycosaminoglycans of the extracellular matrix. J Biol Chem. 2000 Oct 6;275(40):31226-32. [PubMed:10900194 ]
  8. Subramanian G, LeBlanc RA, Wardley RC, Fuller AO: Defective entry of herpes simplex virus types 1 and 2 into porcine cells and lack of infection in infant pigs indicate species tropism. J Gen Virol. 1995 Sep;76 ( Pt 9):2375-9. [PubMed:7561780 ]
  9. Jenniskens GJ, Veerkamp JH, van Kuppevelt TH: Heparan sulfates in skeletal muscle development and physiology. J Cell Physiol. 2006 Feb;206(2):283-94. [PubMed:15991249 ]
  10. Maeda T, Alexander CM, Friedl A: Induction of syndecan-1 expression in stromal fibroblasts promotes proliferation of human breast cancer cells. Cancer Res. 2004 Jan 15;64(2):612-21. [PubMed:14744776 ]
  11. Sher I, Zisman-Rozen S, Eliahu L, Whitelock JM, Maas-Szabowski N, Yamada Y, Breitkreutz D, Fusenig NE, Arikawa-Hirasawa E, Iozzo RV, Bergman R, Ron D: Targeting perlecan in human keratinocytes reveals novel roles for perlecan in epidermal formation. J Biol Chem. 2006 Feb 24;281(8):5178-87. Epub 2005 Nov 2. [PubMed:16269412 ]
  12. Savas PS, Hemsley KM, Hopwood JJ: Intracerebral injection of sulfamidase delays neuropathology in murine MPS-IIIA. Mol Genet Metab. 2004 Aug;82(4):273-85. [PubMed:15308125 ]
  13. Chernousov MA, Rothblum K, Tyler WA, Stahl RC, Carey DJ: Schwann cells synthesize type V collagen that contains a novel alpha 4 chain. Molecular cloning, biochemical characterization, and high affinity heparin binding of alpha 4(V) collagen. J Biol Chem. 2000 Sep 8;275(36):28208-15. [PubMed:10852920 ]
  14. Chikama S, Iida S, Inoue M, Kawagoe N, Tomiyasu K, Matsuoka K, Noda S, Takazono I: Role of heparan sulfate proteoglycan (syndecan-1) on the renal epithelial cells during calcium oxalate monohydrate crystal attachment. Kurume Med J. 2002;49(4):201-10. [PubMed:12652971 ]
  15. Kosir MA, Foley-Loudon PA, Finkenauer R, Tennenberg SD: Multiple heparanases are expressed in polymorphonuclear cells. J Surg Res. 2002 Mar;103(1):100-8. [PubMed:11855924 ]
  16. Myette JR, Shriver Z, Liu J, Venkataraman G, Rosenberg R, Sasisekharan R: Expression in Escherichia coli, purification and kinetic characterization of human heparan sulfate 3-O-sulfotransferase-1. Biochem Biophys Res Commun. 2002 Feb 1;290(4):1206-13. [PubMed:11811991 ]
  17. Barnett MW, Fisher CE, Perona-Wright G, Davies JA: Signalling by glial cell line-derived neurotrophic factor (GDNF) requires heparan sulphate glycosaminoglycan. J Cell Sci. 2002 Dec 1;115(Pt 23):4495-503. [PubMed:12414995 ]
  18. Haimov-Kochman R, Friedmann Y, Prus D, Goldman-Wohl DS, Greenfield C, Anteby EY, Aviv A, Vlodavsky I, Yagel S: Localization of heparanase in normal and pathological human placenta. Mol Hum Reprod. 2002 Jun;8(6):566-73. [PubMed:12029075 ]
  19. Leu SJ, Chen N, Chen CC, Todorovic V, Bai T, Juric V, Liu Y, Yan G, Lam SC, Lau LF: Targeted mutagenesis of the angiogenic protein CCN1 (CYR61). Selective inactivation of integrin alpha6beta1-heparan sulfate proteoglycan coreceptor-mediated cellular functions. J Biol Chem. 2004 Oct 15;279(42):44177-87. Epub 2004 Aug 17. [PubMed:15322081 ]
  20. Lensen JF, Rops AL, Wijnhoven TJ, Hafmans T, Feitz WF, Oosterwijk E, Banas B, Bindels RJ, van den Heuvel LP, van der Vlag J, Berden JH, van Kuppevelt TH: Localization and functional characterization of glycosaminoglycan domains in the normal human kidney as revealed by phage display-derived single chain antibodies. J Am Soc Nephrol. 2005 May;16(5):1279-88. Epub 2005 Mar 23. [PubMed:15788473 ]

Only showing the first 10 proteins. There are 13 proteins in total.

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:
UGT2B4
Uniprot ID:
P06133
Molecular weight:
60512.035
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:
UGT1A4
Uniprot ID:
P22310
Molecular weight:
60024.535
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:
UGT2B7
Uniprot ID:
P16662
Molecular weight:
60720.15
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:
UGT1A9
Uniprot ID:
O60656
Molecular weight:
59940.495
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:
UGT1A6
Uniprot ID:
P19224
Molecular weight:
60750.215
General function:
Involved in galactosylgalactosylxylosylprotein 3-beta-glucuronosyltransferase activity
Specific function:
Glycosaminoglycans biosynthesis. Involved in forming the linkage tetrasaccharide present in heparan sulfate and chondroitin sulfate. Transfers a glucuronic acid moiety from the uridine diphosphate-glucuronic acid (UDP-GlcUA) to the common linkage region trisaccharide Gal-beta-1,3-Gal-beta-1,4-Xyl covalently bound to a Ser residue at the glycosaminylglycan attachment site of proteoglycans. Can also play a role in the biosynthesis of l2/HNK-1 carbohydrate epitope on glycoproteins. Shows strict specificity for Gal-beta-1,3-Gal-beta-1,4-Xyl, exhibiting negligible incorporation into other galactoside substrates including Galbeta1-3Gal beta1-O-benzyl, Galbeta1-4GlcNAc and Galbeta1-4Glc.
Gene Name:
B3GAT3
Uniprot ID:
O94766
Molecular weight:
37121.52
General function:
Involved in catalytic activity
Specific function:
Required for the lysosomal degradation of heparan sulfate and dermatan sulfate.
Gene Name:
IDS
Uniprot ID:
P22304
Molecular weight:
Not Available
General function:
Involved in cell adhesion
Specific function:
The LG3 peptide has anti-angiogenic properties that require binding of calcium ions for full activity
Gene Name:
HSPG2
Uniprot ID:
P98160
Molecular weight:
468794.4
General function:
Involved in cytoskeletal protein binding
Specific function:
Cell surface proteoglycan that bears both heparan sulfate and chondroitin sulfate and that links the cytoskeleton to the interstitial matrix
Gene Name:
SDC1
Uniprot ID:
P18827
Molecular weight:
32461.4

Only showing the first 10 proteins. There are 13 proteins in total.