Details of the Drug

General Information of Drug (ID: DM8IC5H)

Drug Name
TRICIRIBINE
Synonyms
NSC154020; Akt Inhibitor V, Triciribine; MLS002702033; Akt/PKB Signaling Inhibitor-2; NSC-154020; TCN; Akt inhibitor V; AC1Q7CGY; AC1L6DVE; tricyclic nucleoside (TCN); SCHEMBL61269; GTPL5920; CHEMBL1892348; CHEBI:91697; HMS3268N05; HMS3654C06; HMS3229A09; HSCI1_000386; CCG-206732; 5-methyl-1-pentofuranosyl-1,5-dihydro-1,4,5,6,8-pentaazaacenaphthylen-3-amine; SMR001565606; SC-89664; NCI60_001091; Akt/protein kinase B signaling inhibitor-2; BRD-A42649439-001-01-0; BRD-A42649439-001-02-8; 1,5,6,8-Pentaazaacennaphthylen-3-amine, 1,5-dih
Indication
Disease Entry ICD 11 Status REF
Solid tumour/cancer 2A00-2F9Z Phase 1/2 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 320.3
Logarithm of the Partition Coefficient (xlogp) -1.6
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 8
Chemical Identifiers
Formula
C13H16N6O4
IUPAC Name
(2R,3R,4S,5R)-2-(5-amino-7-methyl-2,6,7,9,11-pentazatricyclo[6.3.1.04,12]dodeca-1(12),3,5,8,10-pentaen-2-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Canonical SMILES
CN1C2=NC=NC3=C2C(=CN3[C@H]4[C@@H]([C@@H]([C@H](O4)CO)O)O)C(=N1)N
InChI
InChI=1S/C13H16N6O4/c1-18-11-7-5(10(14)17-18)2-19(12(7)16-4-15-11)13-9(22)8(21)6(3-20)23-13/h2,4,6,8-9,13,20-22H,3H2,1H3,(H2,14,17)/t6-,8-,9-,13-/m1/s1
InChIKey
HOGVTUZUJGHKPL-HTVVRFAVSA-N
Cross-matching ID
PubChem CID
65399
ChEBI ID
CHEBI:65310
CAS Number
35943-35-2
DrugBank ID
DB12405
TTD ID
D04GSV
INTEDE ID
DR1821
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
Human immunodeficiency virus Reverse transcriptase (HIV RT) TT84ETX POL_HV1B1 Inhibitor [2]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Adenosine kinase (ADK)
Main DME 		DE7T5VX ADK_HUMAN Substrate [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Gene/Protein Processing [4]
Follitropin subunit beta (FSHB) OTGLS283 FSHB_HUMAN Gene/Protein Processing [5]
Histone H2AX (H2AX) OT18UX57 H2AX_HUMAN Gene/Protein Processing [4]
Poly polymerase 1 (PARP1) OT310QSG PARP1_HUMAN Gene/Protein Processing [4]
RAC-alpha serine/threonine-protein kinase (AKT1) OT8H2YY7 AKT1_HUMAN Post-Translational Modifications [6]
RAC-beta serine/threonine-protein kinase (AKT2) OTBB632K AKT2_HUMAN Post-Translational Modifications [6]
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: 5920).
2 Design, synthesis and antiviral activity of novel 4,5-disubstituted 7-(beta-D-ribofuranosyl)pyrrolo[2,3-d][1,2,3]triazines and the novel 3-amino-5-... J Med Chem. 2005 Jun 2;48(11):3840-51.
3 Phosphorylation of triciribine is necessary for activity against HIV type 1. AIDS Res Hum Retroviruses. 1998 Oct 10;14(15):1315-22.
4 Metformin and epothilone A treatment up regulate pro-apoptotic PARP-1, Casp-3 and H2AX genes and decrease of AKT kinase level to control cell death of human hepatocellular carcinoma and ovary adenocarcinoma cells. Toxicol In Vitro. 2018 Mar;47:48-62. doi: 10.1016/j.tiv.2017.11.001. Epub 2017 Nov 5.
5 Inhibitory roles of prohibitin and chemerin in FSH-induced rat granulosa cell steroidogenesis. Endocrinology. 2013 Feb;154(2):956-67. doi: 10.1210/en.2012-1836. Epub 2012 Dec 18.
6 Preclinical testing of the Akt inhibitor triciribine in T-cell acute lymphoblastic leukemia. J Cell Physiol. 2011 Mar;226(3):822-31. doi: 10.1002/jcp.22407.