beloranib   Click here for help

GtoPdb Ligand ID: 8445

Synonyms: CKD-732 [2] | O-(4-(2-Dimethylaminoethoxy)-trans-cinnamoyl)fumagillol | ZGN 440 | ZGN-440
Compound class: Synthetic organic
Comment: Beloranib is an investigational drug candidate for the treatment of obesity. The compound is a synthetic derivative of the antimicrobial agent fumagillin, from Aspergillus fumigatus. Beloranib is administered by subcutaneous injection.
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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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 6
Hydrogen bond donors 0
Rotatable bonds 12
Topological polar surface area 73.06
Molecular weight 499.29
XLogP 3.91
No. Lipinski's rules broken 1

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 COC1C(CCC2(C1C1(C)OC1CC=C(C)C)CO2)OC(=O)C=Cc1ccc(cc1)OCCN(C)C
Isomeric SMILES CO[C@@H]1[C@@H](CC[C@@]2([C@H]1[C@@]1(C)O[C@@H]1CC=C(C)C)CO2)OC(=O)/C=C/c1ccc(cc1)OCCN(C)C
InChI InChI=1S/C29H41NO6/c1-20(2)7-13-24-28(3,36-24)27-26(32-6)23(15-16-29(27)19-34-29)35-25(31)14-10-21-8-11-22(12-9-21)33-18-17-30(4)5/h7-12,14,23-24,26-27H,13,15-19H2,1-6H3/b14-10+/t23-,24-,26-,27-,28+,29+/m1/s1
InChI Key ZEZFKUBILQRZCK-MJSCXXSSSA-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/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
[(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl] (E)-3-[4-(2-dimethylaminoethoxy)phenyl]prop-2-enoate
International Nonproprietary Names Click here for help
INN number INN
9056 beloranib
Synonyms Click here for help
CKD-732 [2] | O-(4-(2-Dimethylaminoethoxy)-trans-cinnamoyl)fumagillol | ZGN 440 | ZGN-440
Database Links Click here for help
CAS Registry No. 251111-30-5
GtoPdb PubChem SID 252166655
PubChem CID 6918502
Search Google for chemical match using the InChIKey ZEZFKUBILQRZCK-MJSCXXSSSA-N
Search Google for chemicals with the same backbone ZEZFKUBILQRZCK
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UniChem Compound Search for chemical match using the InChIKey ZEZFKUBILQRZCK-MJSCXXSSSA-N
UniChem Connectivity Search for chemical match using the InChIKey ZEZFKUBILQRZCK-MJSCXXSSSA-N