heparin   Click here for help

GtoPdb Ligand ID: 4214

Synonyms: HepFlush®
Approved drug
heparin is an approved drug (FDA (1939))
Comment: The exact structure of commercial heparin varies according to the conformation of its disaccharide subunits. Heparin is a polymer made up from carbohydrate subunits. The structure shown here matches the structure for the CAS registry number 9005-49-6. A natural product, found in various species, heparin is used clinically as an anti-coagulant. Commercial preparations usually vary in size from 12-15 kDa, while a low molecular weight variant is also available. Database entries may specify the sodium salt forms.
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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
SMILES / InChI / InChIKey
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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
InChI Key ZFGMDIBRIDKWMY-PASTXAENSA-N
Classification Click here for help
Compound class Metabolite or derivative
Approved drug? Yes (FDA (1939))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
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
HepFlush®
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
ChEBI CHEBI:28304
ChEMBL Ligand CHEMBL526514
DrugBank Ligand DB01109
GtoPdb PubChem SID 178101031
PubChem CID 22833565
Search Google for chemical match using the InChIKey ZFGMDIBRIDKWMY-PASTXAENSA-N
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Search PubMed clinical trials heparin sodium
Search PubMed titles heparin sodium
Search PubMed titles/abstracts heparin sodium
Search UniChem for chemical match using the InChIKey ZFGMDIBRIDKWMY-PASTXAENSA-N
Search UniChem for chemicals with the same backbone ZFGMDIBRIDKWMY
Wikipedia Heparin