ID: ALA2012686

Max Phase: Preclinical

Molecular Formula: C18H22ClN5O2

Molecular Weight: 375.86

Molecule Type: Small molecule

Representations

Synonyms (1): MRS-5474
Synonyms from Alternative Forms(1):

Canonical SMILES:  O[C@@H]1[C@H](O)[C@@H]2C[C@@H]2[C@H]1n1cnc2c(NC(C3CC3)C3CC3)nc(Cl)nc21

Standard InChI:  InChI=1S/C18H22ClN5O2/c19-18-22-16(21-11(7-1-2-7)8-3-4-8)12-17(23-18)24(6-20-12)13-9-5-10(9)14(25)15(13)26/h6-11,13-15,25-26H,1-5H2,(H,21,22,23)/t9-,10+,13+,14+,15-/m0/s1

Standard InChI Key:  XJBGUZYJXHUHPS-HLXQIYJLSA-N

Molecule Features

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

Properties

Molecular Weight: 375.86

Molecular Weight (Monoisotopic): 375.1462

AlogP: 1.99

#Rotatable Bonds: 5

Polar Surface Area: 96.09

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.35

CX Basic pKa: 1.74

CX LogP: 1.55

CX LogD: 1.55

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.69

Np Likeness Score: 0.06

References

1. Tosh DK, Phan K, Deflorian F, Wei Q, Gao ZG, Jacobson KA..  (2011)  Truncated (N)-Methanocarba Nucleosides as A(1) Adenosine Receptor Agonists and Partial Agonists: Overcoming Lack of a Recognition Element.,  2  (8): [PMID:21858244] [10.1021/ml200114q]

2. Tosh DK, Paoletta S, Deflorian F, Phan K, Moss SM, Gao ZG, Jiang X, Jacobson KA..  (2012)  Structural sweet spot for A1 adenosine receptor activation by truncated (N)-methanocarba nucleosides: receptor docking and potent anticonvulsant activity.,  55  (18): [PMID:22921089] [10.1021/jm300965a]

3. Tosh DK, Ciancetta A, Warnick E, Crane S, Gao ZG, Jacobson KA..  (2016)  Structure-Based Scaffold Repurposing for G Protein-Coupled Receptors: Transformation of Adenosine Derivatives into 5HT2B/5HT2C Serotonin Receptor Antagonists.,  59  (24): [PMID:27933810] [10.1021/acs.jmedchem.6b01183]

4. Yu J, Mannes P, Jung YH, Ciancetta A, Bitant A, Lieberman DI, Khaznadar S, Auchampach JA, Gao ZG, Jacobson KA..  (2018)  Structure activity relationship of 2-arylalkynyl-adenine derivatives as human A₃ adenosine receptor antagonists.,  9  (11): [PMID:30568760] [10.1039/C8MD00317C]

5. Tosh DK, Rao H, Bitant A, Salmaso V, Mannes P, Lieberman DI, Vaughan KL, Mattison JA, Rothwell AC, Auchampach JA, Ciancetta A, Liu N, Cui Z, Gao ZG, Reitman ML, Gavrilova O, Jacobson KA..  (2019)  Design and in Vivo Characterization of A₁ Adenosine Receptor Agonists in the Native Ribose and Conformationally Constrained (N)-Methanocarba Series.,  62  (3): [PMID:30605331] [10.1021/acs.jmedchem.8b01662]

6. Tosh DK,Toti KS,Hurst BL,Julander JG,Jacobson KA.  (2020)  Structure activity relationship of novel antiviral nucleosides against Enterovirus A71.,  30  (23): [PMID:33031923] [10.1016/j.bmcl.2020.127599]

Source

Source(1):

• Scientific Literature