Details of the Drug

General Information of Drug (ID: DMKYXJW)

Drug Name
Dorsomorphin
Synonyms
dorsomorphin; 866405-64-3; 6-(4-(2-(Piperidin-1-yl)ethoxy)phenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine; BML-275; Compound C; AMPK Inhibitor, Compound C; 6-[4-(2-Piperidin-1-ylethoxy)phenyl]-3-pyridin-4-ylpyrazolo[1,5-a]pyrimidine; CHEMBL478629; CHEBI:78510; 4-(6-{4-[2-(piperidin-1-yl)ethoxy]phenyl}pyrazolo[1,5-a]pyrimidin-3-yl)pyridine; 6-[4-(2-Piperidin-1-yl-ethoxy)-phenyl)]-3-pyridin-4-yl-pyrrazolo[1,5-a]-pyrimidine; AMPK Inhibitor
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 399.5
Logarithm of the Partition Coefficient (xlogp) 3.4
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C24H25N5O
IUPAC Name
6-[4-(2-piperidin-1-ylethoxy)phenyl]-3-pyridin-4-ylpyrazolo[1,5-a]pyrimidine
Canonical SMILES
C1CCN(CC1)CCOC2=CC=C(C=C2)C3=CN4C(=C(C=N4)C5=CC=NC=C5)N=C3
InChI
InChI=1S/C24H25N5O/c1-2-12-28(13-3-1)14-15-30-22-6-4-19(5-7-22)21-16-26-24-23(17-27-29(24)18-21)20-8-10-25-11-9-20/h4-11,16-18H,1-3,12-15H2
InChIKey
XHBVYDAKJHETMP-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
11524144
ChEBI ID
CHEMBL478629
CAS Number
866405-64-3
UNII
10K52CIC1Z
DrugBank ID
DB08597
TTD ID
D0Y0BK
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
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
AMP-activated protein kinase (AMPK) TTLAFZV AAPK1_HUMAN ; AAKB1_HUMAN ; AAKG1_HUMAN Inhibitor [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
5'-AMP-activated protein kinase catalytic subunit alpha-1 (PRKAA1) OT7TNF0L AAPK1_HUMAN Gene/Protein Processing [3]
Acetyl-CoA carboxylase 1 (ACACA) OT5CQPZY ACACA_HUMAN Gene/Protein Processing [4]
Bcl-2-like protein 1 (BCL2L1) OTRC5K9O B2CL1_HUMAN Gene/Protein Processing [3]
Bone morphogenetic protein receptor type-1A (BMPR1A) OTQOA4ZH BMR1A_HUMAN Gene/Protein Processing [5]
Bone morphogenetic protein receptor type-1B (BMPR1B) OTGFN0OD BMR1B_HUMAN Gene/Protein Processing [5]
Cyclin-dependent kinase inhibitor 1 (CDKN1A) OTQWHCZE CDN1A_HUMAN Gene/Protein Processing [6]
Endoplasmic reticulum membrane sensor NFE2L1 (NFE2L1) OT1QHOS2 NF2L1_HUMAN Gene/Protein Processing [4]
Eukaryotic translation initiation factor 2 subunit 1 (EIF2S1) OTM0GDTP IF2A_HUMAN Post-Translational Modifications [7]
Forkhead box protein P3 (FOXP3) OTA9Z9OC FOXP3_HUMAN Gene/Protein Processing [3]
Hemojuvelin (HJV) OT4235J2 RGMC_HUMAN Gene/Protein Processing [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction 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: 4907).
2 The rational design of a novel potent analogue of the 5'-AMP-activated protein kinase inhibitor compound C with improved selectivity and cellular a... Bioorg Med Chem Lett. 2010 Nov 15;20(22):6394-9.
3 Compound C induces autophagy and apoptosis in parental and hydroquinone-selected malignant leukemia cells through the ROS/p38 MAPK/AMPK/TET2/FOXP3 axis. Cell Biol Toxicol. 2020 Aug;36(4):315-331. doi: 10.1007/s10565-019-09495-3. Epub 2020 Jan 3.
4 Metformin leads to accumulation of reactive oxygen species by inhibiting the NFE2L1 expression in human hepatocellular carcinoma cells. Toxicol Appl Pharmacol. 2021 Jun 1;420:115523. doi: 10.1016/j.taap.2021.115523. Epub 2021 Apr 8.
5 A HAMP promoter bioassay system for identifying chemical compounds that modulate hepcidin expression. Exp Hematol. 2015 May;43(5):404-413.e5. doi: 10.1016/j.exphem.2015.01.005. Epub 2015 Jan 26.
6 p53 modulates the AMPK inhibitor compound C induced apoptosis in human skin cancer cells. Toxicol Appl Pharmacol. 2013 Feb 15;267(1):113-24. doi: 10.1016/j.taap.2012.12.016. Epub 2012 Dec 27.
7 Acute exposure to resveratrol inhibits AMPK activity in human skeletal muscle cells. Diabetologia. 2012 Nov;55(11):3051-60. doi: 10.1007/s00125-012-2691-1. Epub 2012 Aug 17.