Details of the Drug

General Information of Drug (ID: DMZRQU7)

Drug Name
[3H]cAMP
Synonyms
Cyclic AMP; cAMP; 60-92-4; Adenosine 3',5'-cyclic monophosphate; 3',5'-cyclic AMP; Adenosine 3',5'-phosphate; Adenosine 3',5'-cyclophosphate; cyclic 3',5'-AMP; Adenosine cyclic monophosphate; cyclic 3',5'-Adenylic acid; Adenosine 3',5'-monophosphate; Adenosine-3',5'-cyclophosphate; Adenosine cyclophosphate; Cyclic Adenosine Monophosphate; cyclic Adenosine 3',5'-phosphate; Cyclic adenylic acid; Adenosine cyclic 3',5'-monophosphate; 3',5'-AMP; cyclic Adenosine 3',5'-monophosphate; Adenosine cyclic 3',5'-phosphate; [3H]-cAMP
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Affected Organisms
Humans and other mammals
Drug Type
Small molecular drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 329.21
Logarithm of the Partition Coefficient (xlogp) -2.6
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 10
Chemical Identifiers
Formula
C10H12N5O6P
IUPAC Name
(4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
Canonical SMILES
C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C(N=CN=C43)N)O)OP(=O)(O1)O
InChI
InChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
InChIKey
IVOMOUWHDPKRLL-KQYNXXCUSA-N
Cross-matching ID
PubChem CID
6076
ChEBI ID
CHEMBL316966
CAS Number
60-92-4
UNII
E0399OZS9N
DrugBank ID
DB02527
TTD ID
D0UB2J
VARIDT ID
DR00295
INTEDE ID
DR2052
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Adenylate cyclase (ADCY) TT2QM9D NOUNIPROTAC Inhibitor [2]
cAMP protein kinase type II-beta (PRKAR2B) TTW4Y2M KAP3_HUMAN Inhibitor [2]
cAMP-dependent protein kinase A type I (PRKAR1A) TTNAHEX KAP0_HUMAN Inhibitor [2]
Fungal Protein kinase A (Fung ypkA) TTYVI76 Q56921_YEREN Activator [3]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Multidrug resistance-associated protein 5 (ABCC5) DTYVM24 MRP5_HUMAN Substrate [4]
Multidrug resistance-associated protein 4 (ABCC4) DTCSGPB MRP4_HUMAN Substrate [5]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Phosphodiesterase 7B (PDE7B)
Main DME 		DEON3ED PDE7B_HUMAN Substrate [6]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2 (HSD3B2) OT02MSKN 3BHS2_HUMAN Gene/Protein Processing [7]
5-hydroxytryptamine receptor 7 (HTR7) OT44DEWB 5HT7R_HUMAN Regulation of Drug Effects [8]
ATP-binding cassette sub-family C member 4 (ABCC4) OTO27PAL MRP4_HUMAN Regulation of Drug Effects [9]
Beta-1 adrenergic receptor (ADRB1) OTQBWN4U ADRB1_HUMAN Regulation of Drug Effects [10]
Beta-2 adrenergic receptor (ADRB2) OTSDOX4Q ADRB2_HUMAN Biotransformations [11]
Beta-3 adrenergic receptor (ADRB3) OTPMG4V7 ADRB3_HUMAN Regulation of Drug Effects [12]
Calcitonin (CALCA) OTZ11LHB CALC_HUMAN Regulation of Drug Effects [13]
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A (PDE10A) OT74EK7Z PDE10_HUMAN Biotransformations [14]
cAMP-dependent protein kinase catalytic subunit beta (PRKACB) OT6RMDCE KAPCB_HUMAN Drug Response [15]
Choriogonadotropin subunit beta 3 (CGB3) OTVM2SU3 CGB3_HUMAN Regulation of Drug Effects [16]
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: 5096).
2 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
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: 1694).
4 The multidrug resistance protein 5 functions as an ATP-dependent export pump for cyclic nucleotides. J Biol Chem. 2000 Sep 29;275(39):30069-74.
5 cAMP regulates expression of the cyclic nucleotide transporter MRP4 (ABCC4) through the EPAC pathway. Pharmacogenet Genomics. 2014 Oct;24(10):522-6.
6 Cloning and characterization of the human and mouse PDE7B, a novel cAMP-specific cyclic nucleotide phosphodiesterase. Biochem Biophys Res Commun. 2000 May 27;272(1):186-92.
7 Inhibitory effects of cholesterol sulfate on progesterone production in human granulosa-like tumor cell line, KGN. Endocr J. 2008 Jul;55(3):575-81.
8 Presence of a 5-HT7 receptor positively coupled to adenylate cyclase activation in human granulosa-lutein cells. J Clin Endocrinol Metab. 2000 Mar;85(3):1277-86. doi: 10.1210/jcem.85.3.6448.
9 The MRP4/ABCC4 gene encodes a novel apical organic anion transporter in human kidney proximal tubules: putative efflux pump for urinary cAMP and cGMP. J Am Soc Nephrol. 2002 Mar;13(3):595-603.
10 Constitutive activity of the human beta(1)-adrenergic receptor in beta(1)-receptor transgenic mice. Mol Pharmacol. 2001 Oct;60(4):712-7.
11 A polymorphism-specific "memory" mechanism in the (2)-adrenergic receptor. Sci Signal. 2011 Aug 9;4(185):ra53. doi: 10.1126/scisignal.2001681.
12 Comparative pharmacology of human beta-adrenergic receptor subtypes--characterization of stably transfected receptors in CHO cells. Naunyn Schmiedebergs Arch Pharmacol. 2004 Feb;369(2):151-9. doi: 10.1007/s00210-003-0860-y. Epub 2004 Jan 17.
13 Volatile anesthetics inhibit calcitonin gene-related peptide receptor-mediated responses in pithed rats and human neuroblastoma cells. J Pharmacol Exp Ther. 2004 Dec;311(3):1016-22. doi: 10.1124/jpet.104.071936. Epub 2004 Aug 5.
14 Cloning and characterization of a novel human phosphodiesterase that hydrolyzes both cAMP and cGMP (PDE10A). J Biol Chem. 1999 Jun 25;274(26):18438-45. doi: 10.1074/jbc.274.26.18438.
15 Activating PRKACB somatic mutation in cortisol-producing adenomas. JCI Insight. 2018 Apr 19;3(8):e98296. doi: 10.1172/jci.insight.98296. eCollection 2018 Apr 19.
16 Upregulation of peripubertal rat Leydig cell steroidogenesis following 24 h in vitro and in vivo exposure to atrazine. Toxicol Sci. 2010 Nov;118(1):52-60. doi: 10.1093/toxsci/kfq227. Epub 2010 Jul 28.