| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-05-15 14:23:41 -0600 |
| HMDB ID |
HMDB01394 |
| Secondary Accession Numbers |
|
| Metabolite Identification |
|---|
| Common Name |
Heparin |
| Description |
Heparin is a highly acidic mucopolysaccharide formed of equal parts of sulfated D-glucosamine and D-glucuronic acid with sulfaminic bridges. The molecular weight ranges from six to twenty thousand. Heparin occurs in and is obtained from liver, lung, mast cells, etc., of vertebrates. Its function is unknown, but it is used to prevent blood clotting in vivo and vitro, in the form of many different salts. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- alpha-Heparin
- Clivarine
- Heparin Sodium
- Arteven
- Bemiparin
- Certoparin
- Clexane
- Dalteparin
- Enoxaparin
- Eparina
- Fraxiparin
- Heparin
- Heparin sulfate
- Heparinate
- Heparinic acid
- Heparinsodiumsalt
- Thromboliquine
|
| Chemical Formula |
C26H41NO34S4 |
| Average Molecular Weight |
1039.85 |
| Monoisotopic Molecular Weight |
1039.039280225 |
| IUPAC Name |
(2S,3S,4R,5R,6R)-6-{[(2S,3S,4S,5R,6S)-6-{[(2R,3S,4S,5R)-2-carboxy-4,6-dihydroxy-5-(sulfooxy)oxan-3-yl]oxy}-2-hydroxy-4-(sulfomethyl)-5-(sulfooxy)oxan-3-yl]oxy}-3-{[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-[(sulfooxy)methyl]oxan-2-yl]oxy}-4,5-dihydroxyoxane-2-carboxylic acid |
| Traditional IUPAC Name |
(2S,3S,4R,5R,6R)-6-{[(2S,3S,4S,5R,6S)-6-{[(2R,3S,4S,5R)-2-carboxy-4,6-dihydroxy-5-(sulfooxy)oxan-3-yl]oxy}-2-hydroxy-4-(sulfomethyl)-5-(sulfooxy)oxan-3-yl]oxy}-3-{[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-[(sulfooxy)methyl]oxan-2-yl]oxy}-4,5-dihydroxy |
| CAS Registry Number |
9005-49-6 |
| SMILES |
CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](COS(O)(=O)=O)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@@H]2[C@@H](O)O[C@H](O[C@H]3[C@H](O)[C@@H](OS(O)(=O)=O)C(O)O[C@H]3C(O)=O)[C@H](OS(O)(=O)=O)[C@H]2CS(O)(=O)=O)O[C@@H]1C(O)=O |
| InChI Identifier |
InChI=1S/C26H41NO34S4/c1-4(28)27-7-9(30)8(29)6(2-52-63(43,44)45)53-24(7)56-15-10(31)11(32)25(58-19(15)21(36)37)55-13-5(3-62(40,41)42)14(60-64(46,47)48)26(59-22(13)38)57-16-12(33)17(61-65(49,50)51)23(39)54-18(16)20(34)35/h5-19,22-26,29-33,38-39H,2-3H2,1H3,(H,27,28)(H,34,35)(H,36,37)(H,40,41,42)(H,43,44,45)(H,46,47,48)(H,49,50,51)/t5-,6+,7+,8+,9+,10+,11+,12-,13-,14+,15-,16-,17+,18+,19-,22-,23?,24+,25+,26-/m0/s1 |
| InChI Key |
ZFGMDIBRIDKWMY-PASTXAENSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Carbohydrates and Carbohydrate Conjugates |
| Class |
Tetrasaccharides |
| Sub Class |
Tetrahexoses |
| Other Descriptors |
- Aliphatic Heteropolycyclic Compounds
|
| Substituents |
- 1,2 Diol
- Acetal
- Alkanesulfonic Acid Derivative
- Carboxamide Group
- Carboxylic Acid
- Dicarboxylic Acid Derivative
- Glucosamine
- Glucuronic Acid Or Derivative
- Glucuronide
- Glycosyl Compound
- Hemiacetal
- Mannosamine
- O Glycosyl Compound
- Organic Sulfuric Acid Monoester
- Oxane
- Secondary Alcohol
- Secondary Carboxylic Acid Amide
- Sugar Acid
- Sulfate Ester
- Sulfonic Acid
- Sulfonyl
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| Direct Parent |
Tetrahexoses |
| Ontology |
|---|
| Status |
Expected and Not Quantified |
| Origin |
|
| Biofunction |
|
| Application |
|
| Cellular locations |
Not Available |
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
Not Available |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
1.08e+01 g/L |
Not Available |
| LogP |
-13.2 |
Not Available |
|
| Predicted Properties |
|
| Spectra |
|---|
|
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| Biological Properties |
|---|
| Cellular Locations |
Not Available
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| Biofluid Locations |
Not Available
|
| Tissue Location |
- Muscle
- Skeletal Muscle
- Bladder
- Fibroblasts
- Intestine
- Neuron
- Pancreas
- Placenta
- Testes
- Kidney
- Liver
- Epidermis
- Thyroid Gland
- Prostate
- Adrenal Gland
- Adipose Tissue
- Adrenal Cortex
- Lung
- Nerve Cells
- Platelet
- Spleen
- Stratum Corneum
- Mast Cell
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| Pathways |
Not Available
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| Normal Concentrations |
|---|
|
Not Available |
| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
DB01109  |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB022599 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
17216115 |
| KEGG Compound ID |
C00374 |
| BioCyc ID |
HEPARIN |
| BiGG ID |
Not Available |
| Wikipedia Link |
Heparin |
| NuGOwiki Link |
HMDB01394 |
| Metagene Link |
HMDB01394 |
| METLIN ID |
Not Available |
| PubChem Compound |
46507594 |
| PDB ID |
Not Available |
| ChEBI ID |
28304 |
| References |
|---|
| Synthesis Reference |
Kuberan, Balagurunathan; Beeler, David L.; Lawrence, Roger; Lech, Miroslaw; Rosenberg, Robert D. Rapid Two-Step Synthesis of Mitrin from Heparosan: A Replacement for Heparin. Journal of the American Chemical Society (2003), 125(41), 12424-12425. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- Betz G, Nowbakht P, Imboden R, Imanidis G: Heparin penetration into and permeation through human skin from aqueous and liposomal formulations in vitro. Int J Pharm. 2001 Oct 9;228(1-2):147-59.
Pubmed: 11576777
- Sun Y, Chai TC: Effects of dimethyl sulphoxide and heparin on stretch-activated ATP release by bladder urothelial cells from patients with interstitial cystitis. BJU Int. 2002 Sep;90(4):381-5.
Pubmed: 12175393
- Kandrotas RJ: Heparin pharmacokinetics and pharmacodynamics. Clin Pharmacokinet. 1992 May;22(5):359-74.
Pubmed: 1505142
- Delhumeau A, Moreau X, Chapotte C, Houi N, Bigorgne JC: Heparin-associated thrombocytopenia syndrome: an underestimated etiology of adrenal hemorrhage. Intensive Care Med. 1993;19(8):475-7.
Pubmed: 8294632
- Lortat-Jacob H, Brisson C, Guerret S, Morel G: Non-receptor-mediated tissue localization of human interferon-gamma: role of heparan sulfate/heparin-like molecules. Cytokine. 1996 Jul;8(7):557-66.
Pubmed: 8891437
- Harig F, Meier C, Hakami L, Strasser R, Bretzger J, Munch F, Vestweber-Wilmes E, Singer H, Weyand M, Cesnjevar R: Does the additional use of heparin-coated extracorporeal circuits (ECC) optimize the effect of modified ultrafiltration (MUF) in pediatric perfusion? Thorac Cardiovasc Surg. 2006 Apr;54(3):168-72.
Pubmed: 16639677
- Tonda R, Galan AM, Pino M, Hernandez MR, Ayats C, Pomar JL, Ordinas A, Escolar G: In vitro evaluation of platelet reactivity toward annuloplasty devices treated with heparin coating: studies under flow conditions. J Biomed Mater Res A. 2005 Oct 1;75(1):192-8.
Pubmed: 16044416
- Haram K, Bjorge L, Sandset PM: Successful preconceptional prophylactic treatment with combined acetyl salicylic acid and low-molecular heparin (Fragmin) in a case of antiphospholipid-antibody syndrome with prior life-threatening hemolysis, elevated liver enzymes and low-platelet syndrome: a case report. Acta Obstet Gynecol Scand. 2005 Dec;84(12):1213-4.
Pubmed: 16305714
- Harding SA, Din JN, Sarma J, Josephs DH, Fox KA, Newby DE: Promotion of proinflammatory interactions between platelets and monocytes by unfractionated heparin. Heart. 2006 Nov;92(11):1635-8. Epub 2006 May 18.
Pubmed: 16709700
- Christensen K, Larsson R, Emanuelsson H, Elgue G, Larsson A: Effects on blood compatibility in vitro by combining a direct P2Y12 receptor inhibitor and heparin coating of stents. Platelets. 2006 Aug;17(5):318-27.
Pubmed: 16928604
- Applebaum DM, Goldberg AP, Pykalisto OJ, Brunzell JD, Hazzard WR: Effect of estrogen on post-heparin lipolytic activity. Selective decline in hepatic triglyceride lipase. J Clin Invest. 1977 Apr;59(4):601-8.
Pubmed: 845252
- Yeh RW, Everett BM, Foo SY, Dorer DJ, Laposata M, Van Cott EM, Jang IK: Predictors for the development of elevated anti-heparin/platelet factor 4 antibody titers in patients undergoing cardiac catheterization. Am J Cardiol. 2006 Aug 1;98(3):419-21. Epub 2006 Jun 12.
Pubmed: 16860036
- Harel A, Fainaru M, Rubinstein M, Tal N, Schwartz M: Fish apolipoprotein-A-I has heparin binding activity: implication for nerve regeneration. J Neurochem. 1990 Oct;55(4):1237-43.
Pubmed: 2118944
- Bengtsson E, Aspberg A, Heinegard D, Sommarin Y, Spillmann D: The amino-terminal part of PRELP binds to heparin and heparan sulfate. J Biol Chem. 2000 Dec 29;275(52):40695-702.
Pubmed: 11007795
- Brunnee T, Reddigari SR, Shibayama Y, Kaplan AP, Silverberg M: Mast cell derived heparin activates the contact system: a link to kinin generation in allergic reactions. Clin Exp Allergy. 1997 Jun;27(6):653-63.
Pubmed: 9208186
- Weaver JC, Vanbever R, Vaughan TE, Prausnitz MR: Heparin alters transdermal transport associated with electroporation. Biochem Biophys Res Commun. 1997 May 29;234(3):637-40.
Pubmed: 9175766
- Williams MS, Ng'alla LS: Heparin therapy leads to platelet activation and prolongation of PFA-100 closure time. J Cardiovasc Pharmacol Ther. 2005 Dec;10(4):273-80.
Pubmed: 16382263
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