2-amino-9-[(2R,3R,4S,5R)-5-{[({[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphinato]oxy}phosphinato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-7-methyl-6-oxido-9H-purin-7-ium

ID: ALA3351000

PubChem CID: 136845173

Max Phase: Preclinical

Molecular Formula: C21H29N10O18P3

Molecular Weight: 802.44

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Bioactivity Summary Target Summary Assay Summary

Names and Identifiers

Canonical SMILES: C[n+]1cn([C@@H]2O[C@H](COP(=O)(O)OP(=O)([O-])OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(=O)[nH]c(N)nc54)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)c2nc(N)nc(O)c21

Standard InChI: InChI=1S/C21H29N10O18P3/c1-29-5-31(15-9(29)17(37)28-21(23)26-15)19-13(35)11(33)7(47-19)3-45-51(40,41)49-52(42,43)48-50(38,39)44-2-6-10(32)12(34)18(46-6)30-4-24-8-14(30)25-20(22)27-16(8)36/h4-7,10-13,18-19,32-35H,2-3H2,1H3,(H8-,22,23,25,26,27,28,36,37,38,39,40,41,42,43)/t6-,7-,10-,11-,12-,13-,18-,19-/m1/s1

Standard InChI Key: FHHZHGZBHYYWTG-INFSMZHSSA-N

Molfile:

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M  END

Associated Targets(Human)

DCPS Tchem Scavenger mRNA-decapping enzyme DcpS (115 Activities)

Discover Target: DCPS

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

EIF4E Tchem Eukaryotic translation initation factor (600 Activities)

Discover Target: EIF4E

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Eif4e Eukaryotic translation initiation factor 4E (654 Activities)

Discover Target: Eif4e

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

EIF4E Eukaryotic translation initiation factor 4E (100 Activities)

Discover Target: EIF4E

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Natural Product: No	Oral: No	Chemical Probe: No	Parenteral: No
Molecule Type: Small molecule	Topical: No	First In Class: No	Black Box: No
Chirality: No	Availability: No	Prodrug: No

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 802.44	Molecular Weight (Monoisotopic): 802.0874	AlogP: -4.77	#Rotatable Bonds: 12
Polar Surface Area: 421.46	Molecular Species: ACID	HBA: 24	HBD: 10
#RO5 Violations: 3	HBA (Lipinski): 28	HBD (Lipinski): 12	#RO5 Violations (Lipinski): 3
CX Acidic pKa: 0.86	CX Basic pKa: 1.88	CX LogP: -9.66	CX LogD: -14.32
Aromatic Rings: 4	Heavy Atoms: 52	QED Weighted: 0.05	Np Likeness Score: 0.70

References

1. Kowalska J, Lukaszewicz M, Zuberek J, Ziemniak M, Darzynkiewicz E, Jemielity J.. (2009) Phosphorothioate analogs of m7GTP are enzymatically stable inhibitors of cap-dependent translation., 19 (7): [PMID:19269171] [10.1016/j.bmcl.2009.02.053]
2. Rydzik AM, Kulis M, Lukaszewicz M, Kowalska J, Zuberek J, Darzynkiewicz ZM, Darzynkiewicz E, Jemielity J.. (2012) Synthesis and properties of mRNA cap analogs containing imidodiphosphate moiety--fairly mimicking natural cap structure, yet resistant to enzymatic hydrolysis., 20 (5): [PMID:22316555] [10.1016/j.bmc.2012.01.013]
3. Warminski M, Kowalska J, Buck J, Zuberek J, Lukaszewicz M, Nicola C, Kuhn AN, Sahin U, Darzynkiewicz E, Jemielity J.. (2013) The synthesis of isopropylidene mRNA cap analogs modified with phosphorothioate moiety and their evaluation as promoters of mRNA translation., 23 (13): [PMID:23726029] [10.1016/j.bmcl.2013.05.001]
4. Ziemniak M, Kowalska J, Lukaszewicz M, Zuberek J, Wnek K, Darzynkiewicz E, Jemielity J.. (2015) Phosphate-modified analogues of m(7)GTP and m(7)Gppppm(7)G-Synthesis and biochemical properties., 23 (17): [PMID:26264844] [10.1016/j.bmc.2015.07.052]
5. (2009) Inhibition of DCPS,

2-amino-9-[(2R,3R,4S,5R)-5-{[({[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphinato]oxy}phosphinato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-7-methyl-6-oxido-9H-purin-7-ium

Names and Identifiers

Alternative Forms

Associated Targets(Human)

Associated Targets(non-human)

Molecule Features

Drug Indications

Mechanisms of Action

Biocomponents

Calculated Properties

References

Source