(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-((2-aminoethylthio)methyl)tetrahydrofuran-3,4-diol

ID: ALA563938

Chembl Id: CHEMBL563938

PubChem CID: 445762

Max Phase: Preclinical

Molecular Formula: C12H18N6O3S

Molecular Weight: 326.38

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  NCCSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C12H18N6O3S/c13-1-2-22-3-6-8(19)9(20)12(21-6)18-5-17-7-10(14)15-4-16-11(7)18/h4-6,8-9,12,19-20H,1-3,13H2,(H2,14,15,16)/t6-,8-,9-,12-/m1/s1

Standard InChI Key:  APAPOJUCRZTCHD-WOUKDFQISA-N

Alternative Forms

Associated Targets(Human)

DNMT1 Tclin DNA (cytosine-5)-methyltransferase 1 (978 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DNMT3B Tchem DNA (cytosine-5)-methyltransferase 3B (150 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DOT1L Tchem Histone-lysine N-methyltransferase, H3 lysine-79 specific (648 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PNMT Tchem Phenylethanolamine N-methyltransferase (540 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Trypanosoma brucei brucei (13300 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Adra2a Alpha-2a adrenergic receptor (204 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 326.38Molecular Weight (Monoisotopic): 326.1161AlogP: -1.28#Rotatable Bonds: 5
Polar Surface Area: 145.33Molecular Species: BASEHBA: 10HBD: 4
#RO5 Violations: HBA (Lipinski): 9HBD (Lipinski): 6#RO5 Violations (Lipinski): 1
CX Acidic pKa: 12.47CX Basic pKa: 9.71CX LogP: -1.67CX LogD: -3.90
Aromatic Rings: 2Heavy Atoms: 22QED Weighted: 0.49Np Likeness Score: 0.69

References

1. Isakovic L, Saavedra OM, Llewellyn DB, Claridge S, Zhan L, Bernstein N, Vaisburg A, Elowe N, Petschner AJ, Rahil J, Beaulieu N, Gauthier F, MacLeod AR, Delorme D, Besterman JM, Wahhab A..  (2009)  Constrained (l-)-S-adenosyl-l-homocysteine (SAH) analogues as DNA methyltransferase inhibitors.,  19  (10): [PMID:19364644] [10.1016/j.bmcl.2009.03.132]
2. Sufrin JR, Spiess AJ, Marasco CJ, Rattendi D, Bacchi CJ..  (2008)  Novel trypanocidal analogs of 5'-(methylthio)-adenosine.,  52  (1): [PMID:17954686] [10.1128/aac.00480-07]
3. Anglin JL, Deng L, Yao Y, Cai G, Liu Z, Jiang H, Cheng G, Chen P, Dong S, Song Y..  (2012)  Synthesis and structure-activity relationship investigation of adenosine-containing inhibitors of histone methyltransferase DOT1L.,  55  (18): [PMID:22924785] [10.1021/jm300917h]
4. Lu J,Bart AG,Wu Q,Criscione KR,McLeish MJ,Scott EE,Grunewald GL.  (2020)  Structure-Based Drug Design of Bisubstrate Inhibitors of Phenylethanolamine N-Methyltransferase Possessing Low Nanomolar Affinity at Both Substrate Binding Domains.,  63  (22): [PMID:33147410] [10.1021/acs.jmedchem.0c01475]

Source