heparin   Click here for help

GtoPdb Ligand ID: 4214

Synonyms: HepFlush®
Approved drug
heparin is an approved drug (FDA (1939))
Comment: Heparin is an endogenous secretory glycosaminoglycan (GAG) that is released predominantly from connective tissue mast cells. Isolated heparin is used clinically as an anti-coagulant. Structurally, heparins (generally known as unfractionated heparin) are a heterogeneous group of anionic, sulfated GAGs. Commercial preparations usually vary in size from 12-15 kDa, while a low molecular weight (fractionated) versions are also available. Database entries may specify the sodium salt forms.

SARS-CoV-2: There is strong experimental evidence which shows that heparin interacts directly with GAG-binding motifs on the Spike glycoprotein of SARS-CoV-2 [3], and that inhibiting this interaction can reduce SARS-CoV-2 infection of host cells [6,8]. These findings suggest that heparin may offer repurposing potential as a prophylactic COVID-19 therapeutic [2], in addition to its benefit as a treatment for COVID-19-related thrombotic complications.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 35
Hydrogen bond donors 14
Rotatable bonds 19
Topological polar surface area 588.61
Molecular weight 1039.04
XLogP -11.46
No. Lipinski's rules broken 3
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Canonical SMILES CC(=O)NC1C(OC2C(OC(C(C2O)O)OC2C(O)OC(C(C2CS(=O)(=O)O)OS(=O)(=O)O)OC2C(OC(C(C2O)OS(=O)(=O)O)O)C(=O)O)C(=O)O)OC(C(C1O)O)COS(=O)(=O)O
Isomeric SMILES CC(=O)N[C@H]1[C@@H](O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)O)O[C@@H]2[C@@H](O)O[C@@H]([C@@H]([C@H]2CS(=O)(=O)O)OS(=O)(=O)O)O[C@@H]2[C@@H](OC([C@@H]([C@H]2O)OS(=O)(=O)O)O)C(=O)O)C(=O)O)O[C@@H]([C@H]([C@@H]1O)O)COS(=O)(=O)O
InChI 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
Classification Click here for help
Compound class Metabolite or derivative
Approved drug? Yes (FDA (1939))
WHO Essential Medicine WHO Essential Medicines List (EML) (22nd List, 2021). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(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
International Nonproprietary Names Click here for help
INN number INN
392 heparin sodium
Synonyms Click here for help
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9693067
Reactome Reaction Reactome logo R-HSA-140791, R-HSA-140806, R-HSA-140870, R-HSA-140872
Other databases
CAS Registry No. 9005-49-6
ChEMBL Ligand CHEMBL526514
DrugBank Ligand DB01109
GtoPdb PubChem SID 178101031
PubChem CID 22833565
Search Google for chemical match using the InChIKey ZFGMDIBRIDKWMY-PASTXAENSA-N
Search Google for chemicals with the same backbone ZFGMDIBRIDKWMY
Search PubMed clinical trials heparin sodium
Search PubMed titles heparin sodium
Search PubMed titles/abstracts heparin sodium
UniChem Compound Search for chemical match using the InChIKey ZFGMDIBRIDKWMY-PASTXAENSA-N
UniChem Connectivity Search for chemical match using the InChIKey ZFGMDIBRIDKWMY-PASTXAENSA-N
Wikipedia Heparin