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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-20 07:58:54 UTC
HMDB IDHMDB0001394
Secondary Accession Numbers
  • HMDB0005027
  • HMDB0015356
  • HMDB01394
  • HMDB05027
  • HMDB15356
Metabolite 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, lung, mast cells, etc., 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 Molecular WeightNot Available
Monoisotopic Molecular WeightNot 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
Chemical Taxonomy
DescriptionThis compound 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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

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
logP-2.4ALOGPS
logS-2ALOGPS
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Bladder
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Lung
  • Mast Cell
  • Muscle
  • Nerve Cells
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Spleen
  • Stratum Corneum
  • Testes
  • Thyroid Gland
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not SpecifiedNot SpecifiedTaking drug identified by DrugBank entry DB01225 details
BloodDetected and Quantified5.193 +/- 1.635 uMNot SpecifiedNot Specified
Normal
details
UrineExpected but not Quantified Not SpecifiedNot SpecifiedTaking drug identified by DrugBank entry DB01225 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022599
KNApSAcK IDNot Available
Chemspider ID7988167
KEGG Compound IDC00374
BioCyc IDHEPARIN
BiGG IDNot Available
Wikipedia LinkHeparin
METLIN IDNot Available
PubChem Compound46507594
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceKuberan, 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
  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 ]

Only showing the first 10 proteins. There are 34 proteins in total.

Enzymes

General function:
Involved in peroxidase activity
Specific function:
Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity.
Gene Name:
MPO
Uniprot ID:
P05164
Molecular weight:
83867.71
References
  1. Rudolph TK, Rudolph V, Witte A, Klinke A, Szoecs K, Lau D, Heitzer T, Meinertz T, Baldus S: Liberation of vessel adherent myeloperoxidase by enoxaparin improves endothelial function. Int J Cardiol. 2010 Apr 1;140(1):42-7. doi: 10.1016/j.ijcard.2008.10.035. Epub 2008 Dec 2. [PubMed:19049846 ]
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 protein kinase activity
Specific function:
Receptor for basic fibroblast growth factor. Receptor for FGF23 in the presence of KL. A shorter form of the receptor could be a receptor for FGF1 (aFGF)
Gene Name:
FGFR1
Uniprot ID:
P11362
Molecular weight:
91866.9
General function:
Involved in heparin binding
Specific function:
Peptides at the N-terminal of HC-II have chemotactic activity for both monocytes and neutrophils
Gene Name:
SERPIND1
Uniprot ID:
P05546
Molecular weight:
57070.2
General function:
Involved in serine-type endopeptidase inhibitor activity
Specific function:
Most important serine protease inhibitor in plasma that regulates the blood coagulation cascade. AT-III inhibits thrombin as well as factors IXa, Xa and XIa. Its inhibitory activity is greatly enhanced in the presence of heparin
Gene Name:
SERPINC1
Uniprot ID:
P01008
Molecular weight:
52601.9

Only showing the first 10 proteins. There are 34 proteins in total.