enoxaparin   Click here for help

GtoPdb Ligand ID: 6811

Synonyms: Clexane® | enoxaparin sodium | Lovenox® | PK-10169 | RP-54563
Approved drug
enoxaparin is an approved drug (FDA (1993), FDA (2016))
Compound class: Synthetic organic
Comment: A Low-Molecular-Weight Heparin antithrombin-III activator. It consists of fractionated material from pig mucosa but the PubChem structure represents the major form.

Biosimilar drugs: The EMA approved enoxaparin biosimilars named Inhixa and Thorinane in 2016.
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View more information in the IUPHAR Pharmacology Education Project: enoxaparin

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 39
Hydrogen bond donors 15
Rotatable bonds 22
Topological polar surface area 652.39
Molecular weight 1134.01
XLogP -13.27
No. Lipinski's rules broken 3

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES OCC1OC(OC2C(OC(C(C2O)OS(=O)(=O)O)OC2C(COS(=O)(=O)O)OC(C(C2O)NC(=O)C)O)C(=O)O)C(C(C1OC1OC(C(=O)O)C(C(C1OS(=O)(=O)O)O)O)OS(=O)(=O)O)NS(=O)(=O)O
Isomeric SMILES OCC1OC(OC2C(OC(C(C2O)OS(=O)(=O)O)OC2C(COS(=O)(=O)O)OC(C(C2O)NC(=O)C)O)C(=O)O)C(C(C1OC1OC(C(=O)O)C(C(C1OS(=O)(=O)O)O)O)OS(=O)(=O)O)NS(=O)(=O)O
InChI InChI=1S/C26H42N2O37S5/c1-4(30)27-7-9(31)13(6(56-23(7)39)3-55-67(43,44)45)58-26-19(65-70(52,53)54)12(34)16(20(62-26)22(37)38)60-24-8(28-66(40,41)42)15(63-68(46,47)48)14(5(2-29)57-24)59-25-18(64-69(49,50)51)11(33)10(32)17(61-25)21(35)36/h5-20,23-26,28-29,31-34,39H,2-3H2,1H3,(H,27,30)(H,35,36)(H,37,38)(H,40,41,42)(H,43,44,45)(H,46,47,48)(H,49,50,51)(H,52,53,54)
InChI Key HTTJABKRGRZYRN-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. de Haan CA, Li Z, te Lintelo E, Bosch BJ, Haijema BJ, Rottier PJ. (2005)
Murine coronavirus with an extended host range uses heparan sulfate as an entry receptor.
J Virol, 79 (22): 14451-6. [PMID:16254381]
2. Eriksson BI, Söderberg K, Widlund L, Wandeli B, Tengborn L, Risberg B. (1995)
A comparative study of three low-molecular weight heparins (LMWH) and unfractionated heparin (UH) in healthy volunteers.
Thromb Haemost, 73 (3): 398-401. [PMID:7667822]
3. Lang J, Yang N, Deng J, Liu K, Yang P, Zhang G, Jiang C. (2011)
Inhibition of SARS pseudovirus cell entry by lactoferrin binding to heparan sulfate proteoglycans.
PLoS ONE, 6 (8): e23710. [PMID:21887302]