(S)-2-Amino-4-((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)(pent-2-yn-1-yl)amino)butanoic Acid

ID: ALA5202371

PubChem CID: 168292678

Max Phase: Preclinical

Molecular Formula: C19H27N7O5

Molecular Weight: 433.47

Names and Identifiers

Canonical SMILES:  CCC#CCN(CC[C@H](N)C(=O)O)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C19H27N7O5/c1-2-3-4-6-25(7-5-11(20)19(29)30)8-12-14(27)15(28)18(31-12)26-10-24-13-16(21)22-9-23-17(13)26/h9-12,14-15,18,27-28H,2,5-8,20H2,1H3,(H,29,30)(H2,21,22,23)/t11-,12+,14+,15+,18+/m0/s1

Standard InChI Key:  ACRZBOXAKRENTK-URQYDQELSA-N

Molfile:  

 
     RDKit          2D

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    2.7922    0.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1251    0.8477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3799    1.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2046    1.6319    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4594    0.8477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2102    0.5128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8790   -0.4605    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9245    0.9252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5811   -1.0681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3530   -0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4959    1.6496    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9245    0.8248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2101   -0.4123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0672   -0.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7816   -1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  1  1  0
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  6  7  1  0
  3  7  1  1
  7  8  1  0
  8  9  2  0
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 10  6  2  0
 10 11  1  0
 12 11  2  0
 13 12  1  0
 14 13  2  0
  6 14  1  0
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  2 16  1  6
  1 17  1  6
  5 18  1  1
 18 19  1  0
 20 19  1  0
 20 21  1  0
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 19 24  1  0
 22 25  1  1
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 24 28  1  0
 28 29  3  0
 29 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5202371

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 433.47

Molecular Weight (Monoisotopic): 433.2074

AlogP: -1.45

#Rotatable Bonds: 8

Polar Surface Area: 185.87

Molecular Species: ZWITTERION

HBA: 11

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.81

CX Basic pKa: 9.19

CX LogP: -3.22

CX LogD: -3.23

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.31

Np Likeness Score: 0.65

References

1. Schwickert M, Fischer TR, Zimmermann RA, Hoba SN, Meidner JL, Weber M, Weber M, Stark MM, Koch J, Jung N, Kersten C, Windbergs M, Lyko F, Helm M, Schirmeister T..  (2022)  Discovery of Inhibitors of DNA Methyltransferase 2, an Epitranscriptomic Modulator and Potential Target for Cancer Treatment.,  65  (14.0): [PMID:35849534] [10.1021/acs.jmedchem.2c00388]

Source

Source(1):

• Scientific Literature