| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-01-28 19:27:25 -0700 |
| HMDB ID |
HMDB00693 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
Heparan sulfate |
| Description |
Heparan 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- alpha-Idosane
- Heparan N-sulfate
- Heparan N-sulphate
- Heparan sulfate
- Heparan sulphate
- Heparatan sulfate
- Heparatan sulphate
- Heparitin
- Heparitin monosulfate
- Heparitin monosulphate
- Heparitin sulfate
- Heparitin sulphate
- HHS 5
- N-Acetylheparan sulfate
- N-Acetylheparan sulphate
- Suleparoid
- Tavidan
|
| Chemical Formula |
C14H23NO21S3 |
| Average Molecular Weight |
637.522 |
| Monoisotopic Molecular Weight |
636.992468873 |
| IUPAC Name |
(2S,3R,4R,5S,6R)-4-hydroxy-3-methoxy-6-{[(2S,3R,4S,5S,6R)-6-methoxy-4-oxido-5-[(sulfooxy)amino]-2-[(sulfooxy)methyl]oxan-3-yl]oxy}-5-(sulfooxy)oxane-2-carboxylate |
| Traditional IUPAC Name |
(2S,3R,4R,5S,6R)-4-hydroxy-3-methoxy-6-{[(2S,3R,4S,5S,6R)-6-methoxy-4-oxido-5-[(sulfooxy)amino]-2-[(sulfooxy)methyl]oxan-3-yl]oxy}-5-(sulfooxy)oxane-2-carboxylate |
| CAS Registry Number |
9050-30-0 |
| SMILES |
Not Available |
| InChI Identifier |
InChI=1S/C14H24NO21S3/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/h4-11,13-15,17H,3H2,1-2H3,(H,18,19)(H,20,21,22)(H,23,24,25)(H,26,27,28)/q-1/p-1/t4-,5-,6-,7+,8-,9+,10-,11-,13+,14+/m0/s1 |
| InChI Key |
WKPUACLQLIIVJJ-RHKLHVFKSA-M |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Carbohydrates and Carbohydrate Conjugates |
| Class |
Disaccharides |
| Sub Class |
Dihexoses |
| Other Descriptors |
- Aliphatic Heteropolycyclic Compounds
|
| Substituents |
- Acetal
- Carboxylic Acid Salt
- Dialkyl Ether
- Glucosamine
- Glucuronic Acid Or Derivative
- Glucuronide
- Glycosyl Compound
- Mannosamine
- O Glycosyl Compound
- Organic Hydroxylamine
- Organic Hyponitrite
- Organic Sulfuric Acid
- Organic Sulfuric Acid Monoester
- Oxane
- Secondary Alcohol
- Sugar Acid
- Sulfate Ester
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| Direct Parent |
Dihexoses |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
Not Available
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| Application |
Not Available
|
| Cellular locations |
Not Available
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| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
Not Available |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
|
| Predicted Properties |
|
| Spectra |
|---|
|
|
| Biological Properties |
|---|
| Cellular Locations |
Not Available
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| Biofluid Locations |
|
| Tissue Location |
- Muscle
- Skeletal Muscle
- Fibroblasts
- Intestine
- Neuron
- Pancreas
- Placenta
- Testes
- Kidney
- Liver
- Epidermis
- Nerve Cells
- Platelet
- Spleen
- Uterus
|
| Pathways |
Not Available
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| Normal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
0.5 (0.0-1.0) uM |
Adult (>18 years old) |
Both |
Normal
|
|
|
| Abnormal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
2.6 (1.4-6.1) uM |
Adult (>18 years old) |
Both |
Liver disease with gastrointestinal bleeding
|
|
|
| Associated Disorders and Diseases |
|---|
| Disease References |
| Liver disease |
|---|
- 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 IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| DrugBank Metabolite ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB022184 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
Not Available |
| KEGG Compound ID |
C00925 |
| BioCyc ID |
CPD-7177 |
| BiGG ID |
Not Available |
| Wikipedia Link |
Heparan sulfate |
| NuGOwiki Link |
HMDB00693 |
| Metagene Link |
HMDB00693 |
| METLIN ID |
Not Available |
| PubChem Compound |
53477714 |
| PDB ID |
Not Available |
| ChEBI ID |
Not Available |
| References |
|---|
| Synthesis Reference |
Meier, 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 |
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
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