(E)-methyl 3-(4-amino-7-(3-hydroxypropyl)-5-p-tolyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)acrylate

ID: ALA4065469

PubChem CID: 16662748

Max Phase: Preclinical

Molecular Formula: C20H22N4O3

Molecular Weight: 366.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)/C=C/c1c(-c2ccc(C)cc2)c2c(N)ncnc2n1CCCO

Standard InChI:  InChI=1S/C20H22N4O3/c1-13-4-6-14(7-5-13)17-15(8-9-16(26)27-2)24(10-3-11-25)20-18(17)19(21)22-12-23-20/h4-9,12,25H,3,10-11H2,1-2H3,(H2,21,22,23)/b9-8+

Standard InChI Key:  SUWNTOBZXIAHKB-CMDGGOBGSA-N

Molfile:  

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   26.9508   -6.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6656   -7.0983    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.6638   -5.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3792   -5.8544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3841   -6.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1759   -6.9377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.6605   -6.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1680   -5.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4354   -7.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8869   -8.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1464   -9.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5980   -9.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.6613   -4.6204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.4183   -4.8071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2235   -4.6364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4739   -3.8510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   28.8619   -4.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1673   -2.4539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4854   -6.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9021   -6.9697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7271   -6.9647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1438   -7.6767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.1354   -6.2479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.9603   -6.2430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA4065469

   (E)-Methyl 3-(4-amino-7-(3-hydroxypropyl)-5-p-tolyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)acrylate

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

Calculated Properties

Molecular Weight: 366.42

Molecular Weight (Monoisotopic): 366.1692

AlogP: 2.56

#Rotatable Bonds: 6

Polar Surface Area: 103.26

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.05

CX LogP: 2.50

CX LogD: 2.48

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.51

Np Likeness Score: -0.33

References

1. Jackson PA, Widen JC, Harki DA, Brummond KM..  (2017)  Covalent Modifiers: A Chemical Perspective on the Reactivity of α,β-Unsaturated Carbonyls with Thiols via Hetero-Michael Addition Reactions.,  60  (3): [PMID:27996267] [10.1021/acs.jmedchem.6b00788]

Source

Source(1):

• Scientific Literature