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]
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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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEBI:37537
CAS Number: 16561-29-8
UNII: NI40JAQ945
DrugBank ID: DB17045
TTD ID: D09DHT

Repurposed Drugs (RPD)

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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]

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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]
3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMGCR)	OTRT3F3U	HMDH_HUMAN	Gene/Protein Processing	[8]
5-hydroxytryptamine receptor 1A (HTR1A)	OT38K9MK	5HT1A_HUMAN	Gene/Protein Processing	[9]
72 kDa type IV collagenase (MMP2)	OT5NIWA2	MMP2_HUMAN	Gene/Protein Processing	[10]
ADP-ribosylation factor 1 (ARF1)	OT5C4C3L	ARF1_HUMAN	Protein Interaction/Cellular Processes	[11]
ADP-ribosylation factor 6 (ARF6)	OTVV7KJO	ARF6_HUMAN	Protein Interaction/Cellular Processes	[11]
Albumin (ALB)	OTVMM513	ALBU_HUMAN	Gene/Protein Processing	[12]
Aldo-keto reductase family 1 member B10 (AKR1B10)	OTOA4HTH	AK1BA_HUMAN	Gene/Protein Processing	[13]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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	PPAR gamma ligands, troglitazone and pioglitazone, up-regulate expression of HMG-CoA synthase and HMG-CoA reductase gene in THP-1 macrophages. FEBS Lett. 2002 Jun 5;520(1-3):177-81.
9	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.
10	Sulfated glucosamine inhibits MMP-2 and MMP-9 expressions in human fibrosarcoma cells. Bioorg Med Chem. 2007 Jul 15;15(14):4891-6.
11	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.
12	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.
13	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.