Human Metabolome Database Version 3.5

Showing metabocard for Heparin (HMDB01394)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-07-24 11:52:15 -0600
HMDB ID HMDB01394
Secondary Accession Numbers
  • HMDB05027
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 Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. alpha-Heparin
  2. Clivarine
  3. Heparin Sodium
  4. Arteven
  5. Bemiparin
  6. Certoparin
  7. Clexane
  8. Dalteparin
  9. Enoxaparin
  10. Eparina
  11. Fraxiparin
  12. Heparin
  13. Heparin sulfate
  14. Heparin sulphate
  15. Heparinate
  16. Heparinic acid
  17. Heparinsodiumsalt
  18. 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
Direct Parent Tetrahexoses
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Anticoagulants
  • Heparins
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
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
Property Value Source
Water Solubility 14.4 g/L ALOGPS
LogP -1.65 ALOGPS
LogP -15 ChemAxon
LogS -1.86 ALOGPS
pKa (strongest acidic) -2.6 ChemAxon
pKa (strongest basic) -4.4 ChemAxon
Hydrogen Acceptor Count 31 ChemAxon
Hydrogen Donor Count 14 ChemAxon
Polar Surface Area 555.09 A2 ChemAxon
Rotatable Bond Count 18 ChemAxon
Refractivity 182.32 ChemAxon
Polarizability 86.52 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -6 ChemAxon
Spectra
1H NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
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
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB01109 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022599
KNApSAcK ID Not Available
Chemspider ID 17216115 Link_out
KEGG Compound ID C00374 Link_out
BioCyc ID HEPARIN Link_out
BiGG ID Not Available
Wikipedia Link Heparin Link_out
NuGOwiki Link HMDB01394 Link_out
Metagene Link HMDB01394 Link_out
METLIN ID Not Available
PubChem Compound 46507594 Link_out
PDB ID Not Available
ChEBI ID 28304 Link_out
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
  1. 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 Link_out
  2. 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 Link_out
  3. Kandrotas RJ: Heparin pharmacokinetics and pharmacodynamics. Clin Pharmacokinet. 1992 May;22(5):359-74. Pubmed: 1505142 Link_out
  4. 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 Link_out
  5. 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 Link_out
  6. 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 Link_out
  7. 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 Link_out
  8. 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 Link_out
  9. 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 Link_out
  10. 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 Link_out
  11. 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 Link_out
  12. 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 Link_out
  13. 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 Link_out
  14. 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 Link_out
  15. 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 Link_out
  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 Link_out
  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 Link_out

Enzymes
Name: UDP-glucuronosyltransferase 2B4
Reactions: Not Available
Gene Name: UGT2B4
Uniprot ID: P06133 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-4
Reactions: Not Available
Gene Name: UGT1A4
Uniprot ID: P22310 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2B7
Reactions: Not Available
Gene Name: UGT2B7
Uniprot ID: P16662 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-1
Reactions: Not Available
Gene Name: UGT1A1
Uniprot ID: P22309 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-9
Reactions: Not Available
Gene Name: UGT1A9
Uniprot ID: O60656 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-6
Reactions: Not Available
Gene Name: UGT1A6
Uniprot ID: P19224 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Basic fibroblast growth factor receptor 1
Reactions: Not Available
Gene Name: FGFR1
Uniprot ID: P11362 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Heparin cofactor 2
Reactions: Not Available
Gene Name: SERPIND1
Uniprot ID: P05546 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Antithrombin-III
Reactions: Not Available
Gene Name: SERPINC1
Uniprot ID: P01008 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Apolipoprotein E
Reactions: Not Available
Gene Name: APOE
Uniprot ID: P02649 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Amyloid beta A4 protein
Reactions: Not Available
Gene Name: APP
Uniprot ID: P05067 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fibronectin
Reactions: Not Available
Gene Name: FN1
Uniprot ID: P02751 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Apolipoprotein B-100
Reactions: Not Available
Gene Name: APOB
Uniprot ID: P04114 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Heparin-binding growth factor 2
Reactions: Not Available
Gene Name: FGF2
Uniprot ID: P09038 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Vascular endothelial growth factor A
Reactions: Not Available
Gene Name: VEGFA
Uniprot ID: P15692 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Pleiotrophin
Reactions: Not Available
Gene Name: PTN
Uniprot ID: P21246 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Heparin-binding growth factor 1
Reactions: Not Available
Gene Name: FGF1
Uniprot ID: P05230 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Midkine
Reactions: Not Available
Gene Name: MDK
Uniprot ID: P21741 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Proheparin-binding EGF-like growth factor
Reactions: Not Available
Gene Name: HBEGF
Uniprot ID: Q99075 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Keratinocyte growth factor
Reactions: Not Available
Gene Name: FGF7
Uniprot ID: P21781 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Heparanase
Reactions: Not Available
Gene Name: HPSE
Uniprot ID: Q9Y251 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Amyloid-like protein 1
Reactions: Not Available
Gene Name: APLP1
Uniprot ID: P51693 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Azurocidin
Reactions: Not Available
Gene Name: AZU1
Uniprot ID: P20160 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fibroblast growth factor 4
Reactions: Not Available
Gene Name: FGF4
Uniprot ID: P08620 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 60S ribosomal protein L29
Reactions: Not Available
Gene Name: RPL29
Uniprot ID: P47914 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 60S ribosomal protein L22
Reactions: Not Available
Gene Name: RPL22
Uniprot ID: P35268 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fibroblast growth factor 5
Reactions: Not Available
Gene Name: FGF5
Uniprot ID: P12034 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fibroblast growth factor 6
Reactions: Not Available
Gene Name: FGF6
Uniprot ID: P10767 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fibroblast growth factor-binding protein 1
Reactions: Not Available
Gene Name: FGFBP1
Uniprot ID: Q14512 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hepatoma-derived growth factor
Reactions: Not Available
Gene Name: HDGF
Uniprot ID: P51858 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fibroblast growth factor 8
Reactions: Not Available
Gene Name: FGF8
Uniprot ID: P55075 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fibroblast growth factor 3
Reactions: Not Available
Gene Name: FGF3
Uniprot ID: P11487 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA