Details of the Drug

General Information of Drug (ID: DMJWD62)

Drug Name
phorbol 12-myristate 13-acetate
Synonyms TPA; 12-O-tetradecanoylphorbol-13-acetate; tetradecanoyl-beta-phorbol acetate
Indication
Disease Entry ICD 11 Status REF
Acute myeloid leukaemia 2A60 Phase 2 [1]
Hodgkin lymphoma 2B30 Phase 2 [1]
Drug Type
Small molecular drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 3 Molecular Weight (mw) 616.8
Logarithm of the Partition Coefficient (xlogp) 6.5
Rotatable Bond Count (rotbonds) 17
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 8
Chemical Identifiers
Formula
C36H56O8
IUPAC Name
[(1S,2S,6R,10S,11R,13S,14R,15R)-13-acetyloxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] tetradecanoate
Canonical SMILES
CCCCCCCCCCCCCC(=O)O[C@@H]1[C@H]([C@]2([C@@H](C=C(C[C@]3([C@H]2C=C(C3=O)C)O)CO)[C@H]4[C@@]1(C4(C)C)OC(=O)C)O)C
InChI
InChI=1S/C36H56O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-29(39)43-32-24(3)35(42)27(30-33(5,6)36(30,32)44-25(4)38)20-26(22-37)21-34(41)28(35)19-23(2)31(34)40/h19-20,24,27-28,30,32,37,41-42H,7-18,21-22H2,1-6H3/t24-,27+,28-,30-,32-,34-,35-,36-/m1/s1
InChIKey
PHEDXBVPIONUQT-RGYGYFBISA-N
Cross-matching ID
PubChem CID
27924
ChEBI ID
CHEMBL279115
CAS Number
16561-29-8
UNII
NI40JAQ945
DrugBank ID
DB17045
TTD ID
D09DHT
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
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Calcium-activated potassium channel KCa4.1 (KCNT1) TTGJFK1 KCNT1_HUMAN Activator [2]
Calcium-activated potassium channel KCa4.2 (KCNT2) TTLU5FO KCNT2_HUMAN Inhibitor (gating inhibitor) [2]
Inward rectifier potassium channel Kir3.4 (KCNJ5) TTEO25X KCNJ5_HUMAN Inhibitor (gating inhibitor) [3]
Transient receptor potential cation channel V4 (TRPV4) TTKP2SU TRPV4_HUMAN Activator [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-2 (PLCB2) OTPAHDGO PLCB2_HUMAN Protein Interaction/Cellular Processes [5]
15-hydroxyprostaglandin dehydrogenase (HPGD) OTYZI6JB PGDH_HUMAN Gene/Protein Processing [6]
26S proteasome complex subunit SEM1 (SEM1) OTASLBM1 SEM1_HUMAN Gene/Protein Processing [7]
5-hydroxytryptamine receptor 1A (HTR1A) OT38K9MK 5HT1A_HUMAN Gene/Protein Processing [8]
ADP-ribosylation factor 6 (ARF6) OTVV7KJO ARF6_HUMAN Protein Interaction/Cellular Processes [9]
Albumin (ALB) OTVMM513 ALBU_HUMAN Gene/Protein Processing [10]
Aldo-keto reductase family 1 member B10 (AKR1B10) OTOA4HTH AK1BA_HUMAN Gene/Protein Processing [11]
Aldo-keto reductase family 1 member C2 (AKR1C2) OTQ2XMO3 AK1C2_HUMAN Gene/Protein Processing [12]
Alpha-(1,3)-fucosyltransferase 4 (FUT4) OTIBXRTL FUT4_HUMAN Gene/Protein Processing [13]
Amyloid beta precursor like protein 2 (APLP2) OTTFE53M APLP2_HUMAN Protein Interaction/Cellular Processes [14]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
2 Opposite regulation of Slick and Slack K+ channels by neuromodulators. J Neurosci. 2006 May 10;26(19):5059-68.
3 Molecular basis for the inhibition of G protein-coupled inward rectifier K(+) channels by protein kinase C. Proc Natl Acad Sci U S A. 2004 Jan 27;101(4):1087-92.
4 Activation of TRPV4 channels (hVRL-2/mTRP12) by phorbol derivatives. J Biol Chem. 2002 Apr 19;277(16):13569-77.
5 Protein kinase CbetaII activation by 1-beta-D-arabinofuranosylcytosine is antagonistic to stimulation of apoptosis and Bcl-2alpha down-regulation. J Biol Chem. 1997 Sep 19;272(38):23481-4. doi: 10.1074/jbc.272.38.23481.
6 Indomethacin increases 15-PGDH mRNA expression in HL60 cells differentiated by PMA. Prostaglandins Leukot Essent Fatty Acids. 2001 Feb;64(2):87-93. doi: 10.1054/plef.2001.0246.
7 Arsenic exposure in utero exacerbates skin cancer response in adulthood with contemporaneous distortion of tumor stem cell dynamics. Cancer Res. 2008 Oct 15;68(20):8278-85. doi: 10.1158/0008-5472.CAN-08-2099.
8 Mechanisms of regulation of agonist efficacy at the 5-HT(1A) receptor by phospholipid-derived signaling components. J Pharmacol Exp Ther. 2001 Jun;297(3):1025-35.
9 A regulatory role for ADP-ribosylation factor 6 (ARF6) in activation of the phagocyte NADPH oxidase. J Biol Chem. 2000 Oct 20;275(42):32566-71. doi: 10.1074/jbc.M005406200.
10 Atrazine represses S100A4 gene expression and TPA-induced motility in HepG2 cells. Toxicol In Vitro. 2014 Mar;28(2):156-63. doi: 10.1016/j.tiv.2013.10.019. Epub 2013 Nov 6.
11 Down-regulation of aldo-keto reductase AKR1B10 gene expression by a phorbol ester via the ERK/c-Jun signaling pathway. Chem Biol Interact. 2015 Jun 5;234:274-81.
12 Oxidative stress mechanisms do not discriminate between genotoxic and nongenotoxic liver carcinogens. Chem Res Toxicol. 2015 Aug 17;28(8):1636-46.
13 Structurally diverse c-Myc inhibitors share a common mechanism of action involving ATP depletion. Oncotarget. 2015 Jun 30;6(18):15857-70. doi: 10.18632/oncotarget.4327.
14 Shedding of the amyloid precursor protein-like protein APLP2 by disintegrin-metalloproteinases. FEBS J. 2005 Nov;272(22):5808-20. doi: 10.1111/j.1742-4658.2005.04976.x.