heparin   

GtoPdb Ligand ID: 4214

Synonyms: HepFlush®
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.
2D Structure
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Physico-chemical Properties
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
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
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
(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
INN number INN
392 heparin sodium
Synonyms
HepFlush®
Database Links
CAS Registry No. 9005-49-6
ChEBI CHEBI:28304
ChEMBL Ligand CHEMBL526514
DrugBank Ligand DB01109
GtoPdb PubChem SID 178101031
PubChem CID 22833565
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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
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Wikipedia Heparin