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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-06-29 00:47:02 UTC
NP-MRD IDNP0000533
Secondary Accession NumbersNone
Natural Product Identification
Common NameHeparin
DescriptionHeparin is a highly acidic heterogeneous mucopolysaccharide consisting of a variably sulfated repeating disaccharide unit. The most common repeating unit is a trisulfated disaccharide composed of a 2-O-sulfated iduronic acid and 6-O-sulfated, N-sulfated glucosamine, IdoA(2S)-GlcNS(6S). Heparin is formed from equal parts 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, lungs, and mast cells of vertebrates. Its function is unknown, but it is used to prevent blood clotting, in vivo and in vitro, in the form of many different salts. Enoxaparin is a low molecular weight heparin. It is used to prevent and treat deep vein thrombosis or pulmonary embolism, and is given as a subcutaneous injection. Enoxaparin binds to and accelerates the activity of antithrombin III. By activating antithrombin III, enoxaparin preferentially potentiates the inhibition of coagulation factors Xa and IIa. Factor Xa catalyzes the conversion of prothrombin to thrombin, so enoxaparin's inhibition of this process results in decreased thrombin and ultimately the prevention of fibrin clot formation. Low molecular weight heparins are less effective at inactivating factor IIa due to their shorter length compared to unfractionated heparin.
Structure
Thumb
Synonyms
ValueSource
alpha-HeparinHMDB
ClivarineHMDB
Heparin sodiumHMDB
ArtevenHMDB
BemiparinHMDB
CertoparinHMDB
ClexaneHMDB
DalteparinHMDB
EnoxaparinHMDB
EparinaHMDB
FraxiparinHMDB
Heparin sulfateHMDB
Heparin sulphateHMDB
HeparinateHMDB
Heparinic acidHMDB
HeparinsodiumsaltHMDB
ThromboliquineHMDB
Chemical Formula(C12H19NO19S3)nH2O
Average MassNot Available
Monoisotopic MassNot Available
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number9005-49-6
SMILES
[H]O[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](O[C@@H]2O[C@H]([C@@H](O)[C@H](O)[C@H]2OS(O)(=O)=O)C(O)=O)[C@H](O)[C@H]1NS(O)(=O)=O
InChI Identifier
InChI=1S/C12H21NO20S3/c14-4-3(13-34(20,21)22)11(19)30-2(1-29-35(23,24)25)7(4)31-12-9(33-36(26,27)28)6(16)5(15)8(32-12)10(17)18/h2-9,11-16,19H,1H2,(H,17,18)(H,20,21,22)(H,23,24,25)(H,26,27,28)/t2-,3-,4-,5+,6+,7-,8-,9-,11+,12-/m1/s1
InChI KeyOHJKXVLJWUPWQG-PNRHKHKDSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
  • Animalia
  • 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
    • Beta-hydroxy acid
    • Hydroxy acid
    • Sulfuric acid monoamide
    • Oxane
    • Pyran
    • Sulfuric acid monoester
    • Sulfate-ester
    • Sulfuric acid ester
    • Alkyl sulfate
    • Organic sulfuric acid or derivatives
    • Hemiacetal
    • Secondary alcohol
    • Carboxylic acid
    • Organoheterocyclic compound
    • Oxacycle
    • Carboxylic acid derivative
    • Monocarboxylic acid or derivatives
    • Acetal
    • Organopnictogen compound
    • Organonitrogen compound
    • Organic nitrogen compound
    • Organic oxide
    • Carbonyl group
    • Hydrocarbon derivative
    • Alcohol
    • Aliphatic heteromonocyclic compound
    Molecular FrameworkAliphatic heteromonocyclic compounds
    External DescriptorsNot Available
    Physical Properties
    StateSolid
    Experimental Properties
    PropertyValueReference
    Melting PointNot AvailableNot Available
    Boiling PointNot AvailableNot Available
    Water Solubility10.8 g/LNot Available
    LogP-13.2Not Available
    Predicted Properties
    PropertyValueSource
    Water Solubility14.4 g/LALOGPS
    logP10(-2.4) g/LALOGPS
    logS10(-2) g/LALOGPS
    Rule of FiveNoChemAxon
    Ghose FilterNoChemAxon
    HMDB IDHMDB0001394
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB022599
    KNApSAcK IDNot Available
    Chemspider ID7988167
    KEGG Compound IDC00374
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkHeparin
    METLIN IDNot Available
    PubChem Compound9812414
    PDB IDNot Available
    ChEBI ID151315
    Good Scents IDrw1370481
    References
    General References
    1. 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 ]
    2. 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 ]
    3. 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 ]
    4. Kandrotas RJ: Heparin pharmacokinetics and pharmacodynamics. Clin Pharmacokinet. 1992 May;22(5):359-74. [PubMed:1505142 ]
    5. 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 ]
    6. 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 ]
    7. 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 ]
    8. 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 ]
    9. 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 ]
    10. 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 ]
    11. 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 ]
    12. 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 ]
    13. 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 ]
    14. 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 ]
    15. 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 ]
    16. 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 ]
    17. 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 ]