Details of the Drug

General Information of Drug (ID: DMNLQHK)

Drug Name
Tanespimycin
Synonyms
CNF-101; [(3S,5S,6R,7S,8E,10R,11S,12E,14E)-6-Hydroxy-5,11-dimethoxy-3,7,9,15-tetramethyl-16,20,22-trioxo-21-(prop-2-enylamino)-17-azabicyclo[16.3.1]docosa-8,12,14,18,21-pentaen-10-yl] carbamate; [(3R,5S,6R,7S,8E,10S,11S,12Z,14E)-6-hydroxy-5,11-dimethoxy-3,7,9,15-tetramethyl-16,20,22-trioxo-21-(prop-2-enylamino)-17-azabicyclo[16.3.1]docosa-1(21),8,12,14,18-pentaen-10-yl] carbamate; 17AAG, Tanespimycin, Geldanamycin, NSC330507, 17-(Allylamino)-17-demethoxygeldanamycin, CP 127374
Indication
Disease Entry ICD 11 Status REF
Breast cancer 2C60-2C65 Phase 2 [1]
Multiple myeloma 2A83 Discontinued in Phase 3 [1]
Therapeutic Class
Anticancer Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 585.7
Logarithm of the Partition Coefficient (xlogp) 2.6
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 9
Chemical Identifiers
Formula
C31H43N3O8
IUPAC Name
[(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-19-(prop-2-enylamino)-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl] carbamate
Canonical SMILES
C[C@H]1C[C@@H]([C@@H]([C@H](/C=C(/[C@@H]([C@H](/C=C\\C=C(\\C(=O)NC2=CC(=O)C(=C(C1)C2=O)NCC=C)/C)OC)OC(=O)N)\\C)C)O)OC
InChI
InChI=1S/C31H43N3O8/c1-8-12-33-26-21-13-17(2)14-25(41-7)27(36)19(4)15-20(5)29(42-31(32)39)24(40-6)11-9-10-18(3)30(38)34-22(28(21)37)16-23(26)35/h8-11,15-17,19,24-25,27,29,33,36H,1,12-14H2,2-7H3,(H2,32,39)(H,34,38)/b11-9-,18-10+,20-15+/t17-,19+,24+,25+,27-,29+/m1/s1
InChIKey
AYUNIORJHRXIBJ-TXHRRWQRSA-N
Cross-matching ID
PubChem CID
6505803
ChEBI ID
CHEMBL64153
CAS Number
75747-14-7
UNII
4GY0AVT3L4
DrugBank ID
DB05134
TTD ID
D0SC2J
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Heat shock protein 90 alpha (HSP90A) TT78R5H HS90A_HUMAN Inhibitor [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
A disintegrin and metalloproteinase with thrombospondin motifs 1 (ADAMTS1) OTTLJH8W ATS1_HUMAN Gene/Protein Processing [3]
Albumin (ALB) OTVMM513 ALBU_HUMAN Drug Response [4]
Alpha-enolase (ENO1) OTB1KWJS ENOA_HUMAN Gene/Protein Processing [5]
Annexin A1 (ANXA1) OT5OFDJC ANXA1_HUMAN Gene/Protein Processing [5]
Anterior gradient protein 2 homolog (AGR2) OTRRZT7W AGR2_HUMAN Gene/Protein Processing [5]
Apoptotic protease-activating factor 1 (APAF1) OTJWIVY0 APAF_HUMAN Gene/Protein Processing [6]
ATP synthase subunit beta, mitochondrial (ATP5F1B) OTLFZUQK ATPB_HUMAN Gene/Protein Processing [5]
Bcl-2-like protein 1 (BCL2L1) OTRC5K9O B2CL1_HUMAN Gene/Protein Processing [7]
Bcl-2-like protein 11 (BCL2L11) OTNQQWFJ B2L11_HUMAN Gene/Protein Processing [8]
Dehydrogenase/reductase SDR family member 2, mitochondrial (DHRS2) OTFHWIY8 DHRS2_HUMAN Gene/Protein Processing [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

ICD Disease Classification 02 Neoplasm
Disease Class ICD-11: 2C82 Prostate cancer
The Studied Tissue Bone marrow
The Studied Disease Multiple myeloma [ICD-11:2C82]
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Heat shock protein 90 alpha (HSP90A) DTT HSP90AA1 5.98E-06 1.3 4.35
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7751).
2 Tanespimycin: the opportunities and challenges of targeting heat shock protein 90. Expert Opin Investig Drugs. 2009 Jun;18(6):861-8.
3 Candidate therapeutic agents for hepatocellular cancer can be identified from phenotype-associated gene expression signatures. Cancer. 2009 Aug 15;115(16):3738-48. doi: 10.1002/cncr.24417.
4 Stability of the Hsp90 inhibitor 17AAG hydroquinone and prevention of metal-catalyzed oxidation. J Pharm Sci. 2008 Dec;97(12):5147-57. doi: 10.1002/jps.21394.
5 Impact of Heat Shock Protein 90 Inhibition on the Proteomic Profile of Lung Adenocarcinoma as Measured by Two-Dimensional Electrophoresis Coupled with Mass Spectrometry. Cells. 2019 Jul 31;8(8):806. doi: 10.3390/cells8080806.
6 Apoptosis induction in human leukemic cells by a novel protein Bengalin, isolated from Indian black scorpion venom: through mitochondrial pathway and inhibition of heat shock proteins. Chem Biol Interact. 2010 Jan 27;183(2):293-303. doi: 10.1016/j.cbi.2009.11.006. Epub 2009 Nov 12.
7 Analysis of expression of heat shock protein-90 (HSP90) and the effects of HSP90 inhibitor (17-AAG) in multiple myeloma. Leuk Lymphoma. 2006 Jul;47(7):1369-78. doi: 10.1080/10428190500472123.
8 FGFR3 translocations in bladder cancer: differential sensitivity to HSP90 inhibition based on drug metabolism. Mol Cancer Res. 2014 Jul;12(7):1042-54. doi: 10.1158/1541-7786.MCR-14-0004. Epub 2014 Apr 30.