Details of the Drug

General Information of Drug (ID: DMTNQCE)

• Drug Name: L-betagamma-meATP
• Synonyms: UFZTZBNSLXELAL-IOSLPCCCSA-N; AMP-PCP; beta,gamma-Methylene ATP; phosphomethylphosphonic acid adenylate ester; CHEMBL133463; CHEBI:40532; 5'-O-(hydroxy{[hydroxy(phosphonomethyl)phosphoryl]oxy}phosphoryl)adenosine; ADENOSINE 5'-[BETA,GAMMA-METHYLENE]TRIPHOSPHATE; ADENOSINE-5'-[BETA, GAMMA-METHYLENE]TRIPHOSPHATE; 3469-78-1; adenosine 5'-beta,gamma-mu-methylenetriphosphate; ({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}methyl)phosphonic acid; AMPPCP; betagamma-methylene-adenosine 5'-triphosphate; Adenosine-5'-[Beta, Gamma-Methylene]Triphosphate

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1], [2]

• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 4:
  Molecular Weight (mw); 505.21
  Topological Polar Surface Area (xlogp); -5.9
  Rotatable Bond Count (rotbonds); 8
  Hydrogen Bond Donor Count (hbonddonor); 7
  Hydrogen Bond Acceptor Count (hbondacc); 16
• Chemical Identifiers:
  Formula: C11H18N5O12P3
  IUPAC Name: [[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]methylphosphonic acid
  Canonical SMILES: C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)OP(=O)(CP(=O)(O)O)O)O)O)N
  InChI: InChI=1S/C11H18N5O12P3/c12-9-6-10(14-2-13-9)16(3-15-6)11-8(18)7(17)5(27-11)1-26-31(24,25)28-30(22,23)4-29(19,20)21/h2-3,5,7-8,11,17-18H,1,4H2,(H,22,23)(H,24,25)(H2,12,13,14)(H2,19,20,21)/t5-,7-,8-,11-/m1/s1
  InChIKey: UFZTZBNSLXELAL-IOSLPCCCSA-N
• Cross-matching ID:
  PubChem CID: 91532
  ChEBI ID: CHEBI:40532
  CAS Number: 3469-78-1
  DrugBank ID: DB03909
  TTD ID: D0UG4S

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Insulin receptor (INSR)	TTCBFJO	INSR_HUMAN	Inhibitor	[1]
P2X purinoceptor 1 (P2RX1)	TTJW7B3	P2RX1_HUMAN	Agonist	[3]
Pyridoxal kinase (PDXK)	TTXI3KF	PDXK_HUMAN	Inhibitor	[1]

Molecular Expression Atlas of This Drug

• The Studied Disease: Discovery agent
• ICD Disease Classification: N.A.

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Insulin receptor (INSR)	DTT	INSR	1.03E-05	0.26	0.66

References

• [1] How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
• [2] 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: 4236).
• [3] 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. (Target id: 478).
• [4] Trinitrophenyl-substituted nucleotides are potent antagonists selective for P2X1, P2X3, and heteromeric P2X2/3 receptors. Mol Pharmacol. 1998 Jun;53(6):969-73.
• [5] A pyridoxine cyclic phosphate and its 6-azoaryl derivative selectively potentiate and antagonize activation of P2X1 receptors. J Med Chem. 1998 Jun 18;41(13):2201-6.
• [6] Structure-activity relationships of analogues of NF449 confirm NF449 as the most potent and selective known P2X1 receptor antagonist. Eur J Med Chem. 2004 Apr;39(4):345-57.
• [7] New drugs for type 2 diabetes mellitus: what is their place in therapy Drugs. 2008;68(15):2131-62.
• [8] Knockouts model the 100 best-selling drugs--will they model the next 100 Nat Rev Drug Discov. 2003 Jan;2(1):38-51.
• [9] Acidic residues on the N-terminus of proinsulin C-Peptide are important for the folding of insulin precursor. J Biochem. 2002 Jun;131(6):855-9.
• [10] Metformin (Glucophage) inhibits tyrosine phosphatase activity to stimulate the insulin receptor tyrosine kinase. Biochem Pharmacol. 2004 Jun 1;67(11):2081-91.
• [11] Hope for insulin mimetic oral antidiabetic drugs. Eur J Endocrinol. 1999 Dec;141(6):561-2.
• [12] Insulin glulisine: a review of its use in the management of diabetes mellitus. Drugs. 2009;69(8):1035-57.
• [13] 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. (Target id: 1800).