(R,E)-3-(4-(3-(4-((2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)methyl)phenyl)allyl)piperazin-1-yl)propane-1,2-diol

ID: ALA4217603

PubChem CID: 68378925

Max Phase: Preclinical

Molecular Formula: C27H37N5O2

Molecular Weight: 463.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1nn2c(C)cc(C)nc2c1Cc1ccc(/C=C/CN2CCN(C[C@@H](O)CO)CC2)cc1

Standard InChI:  InChI=1S/C27H37N5O2/c1-4-26-25(27-28-20(2)16-21(3)32(27)29-26)17-23-9-7-22(8-10-23)6-5-11-30-12-14-31(15-13-30)18-24(34)19-33/h5-10,16,24,33-34H,4,11-15,17-19H2,1-3H3/b6-5+/t24-/m1/s1

Standard InChI Key:  ABWOWIYOHHZBRY-QQHIZMLBSA-N

Molfile:  

     RDKit          2D

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   15.8944   -9.6851    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1862   -9.2755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.3098   -9.6883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0184   -9.2812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 31 33  1  1
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M  END

Alternative Forms

1. Parent:

   

   ALA4217603

   (2R)-3-[4-[(E)-3-[4-[(2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)methyl]phenyl]prop-2-enyl]piperazin-1-yl]propane-1,2-diol

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: 463.63

Molecular Weight (Monoisotopic): 463.2947

AlogP: 2.48

#Rotatable Bonds: 9

Polar Surface Area: 77.13

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 14.00

CX Basic pKa: 7.65

CX LogP: 2.99

CX LogD: 2.54

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.51

Np Likeness Score: -0.98

References

1. Velcicky J, Miltz W, Oberhauser B, Orain D, Vaupel A, Weigand K, Dawson King J, Littlewood-Evans A, Nash M, Feifel R, Loetscher P..  (2017)  Development of Selective, Orally Active GPR4 Antagonists with Modulatory Effects on Nociception, Inflammation, and Angiogenesis.,  60  (9): [PMID:28445047] [10.1021/acs.jmedchem.6b01703]

Source

Source(1):

• Scientific Literature