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 CDK toolkit. 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
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.

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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
References
1. Chun E, Han CK, Yoon JH, Sim TB, Kim YK, Lee KY. (2005)
Novel inhibitors targeted to methionine aminopeptidase 2 (MetAP2) strongly inhibit the growth of cancers in xenografted nude model.
Int J Cancer, 114 (1): 124-30. [PMID:15523682]
2. Joharapurkar AA, Dhanesha NA, Jain MR. (2014)
Inhibition of the methionine aminopeptidase 2 enzyme for the treatment of obesity.
Diabetes Metab Syndr Obes, 7: 73-84. [PMID:24611021]
3. Kim YM, An JJ, Jin YJ, Rhee Y, Cha BS, Lee HC, Lim SK. (2007)
Assessment of the anti-obesity effects of the TNP-470 analog, CKD-732.
J Mol Endocrinol, 38 (4): 455-65. [PMID:17446235]
4. Lee HS, Choi WK, Son HJ, Lee SS, Kim JK, Ahn SK, Hong CI, Min HK, Kim M, Myung SW. (2004)
Absorption, distribution, metabolism, and excretion of CKD-732, a novel antiangiogenic fumagillin derivative, in rats, mice, and dogs.
Arch Pharm Res, 27 (2): 265-72. [PMID:15029870]
5. McCandless SE, Yanovski JA, Miller J, Fu C, Bird LM, Salehi P, Chan CL, Stafford D, Abuzzahab MJ, Viskochil D et al.. (2017)
Effects of MetAP2 inhibition on hyperphagia and body weight in Prader-Willi syndrome: A randomized, double-blind, placebo-controlled trial.
Diabetes Obes Metab, 19 (12): 1751-1761. [PMID:28556449]
6. Shin SJ, Ahn JB, Park KS, Lee YJ, Hong YS, Kim TW, Kim HR, Rha SY, Roh JK, Kim DH et al.. (2012)
A Phase Ib pharmacokinetic study of the anti-angiogenic agent CKD-732 used in combination with capecitabine and oxaliplatin (XELOX) in metastatic colorectal cancer patients who progressed on irinotecan-based chemotherapy.
Invest New Drugs, 30 (2): 672-80. [PMID:21188464]
7. Yin SQ, Wang JJ, Zhang CM, Liu ZP. (2012)
The development of MetAP-2 inhibitors in cancer treatment.
Curr Med Chem, 19 (7): 1021-35. [PMID:22229417]