(R)-5-(4-(1H-indazol-4-yl)phenyl)-6-((1-(cyclopropanecarbonyl)pyrrolidin-3-yl)methyl)-4,6-diazaspiro[2.4]hept-4-en-7-one

ID: ALA4129431

PubChem CID: 89993632

Max Phase: Preclinical

Molecular Formula: C27H27N5O2

Molecular Weight: 453.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(C1CC1)N1CC[C@@H](CN2C(=O)C3(CC3)N=C2c2ccc(-c3cccc4[nH]ncc34)cc2)C1

Standard InChI:  InChI=1S/C27H27N5O2/c33-25(20-8-9-20)31-13-10-17(15-31)16-32-24(29-27(11-12-27)26(32)34)19-6-4-18(5-7-19)21-2-1-3-23-22(21)14-28-30-23/h1-7,14,17,20H,8-13,15-16H2,(H,28,30)/t17-/m1/s1

Standard InChI Key:  PFUABCQWXXOJGR-QGZVFWFLSA-N

Molfile:  

     RDKit          2D

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   18.1869  -11.9385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.9393   -8.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7436   -8.5084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6832   -7.5620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3562   -9.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5224   -8.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7482  -10.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3637  -10.5266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1843  -10.5200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4316   -9.7375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7638   -9.2605    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1039   -9.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
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 19 18  1  1
 19 20  1  0
 20 21  1  0
 21 22  1  0
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 22 24  1  0
 24 25  1  0
 24 26  2  0
 27 25  1  0
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 25 28  1  0
 16 29  2  0
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 31 32  1  0
 32 33  1  0
 33 34  2  0
 34 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4129431

   6-[[(3R)-1-(cyclopropanecarbonyl)pyrrolidin-3-yl]methyl]-5-[4-(1H-indazol-4-yl)phenyl]-4,6-diazaspiro[2.4]hept-4-en-7-one

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: 453.55

Molecular Weight (Monoisotopic): 453.2165

AlogP: 3.61

#Rotatable Bonds: 5

Polar Surface Area: 81.66

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.95

CX Basic pKa: 3.58

CX LogP: 2.73

CX LogD: 2.73

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.64

Np Likeness Score: -1.14

References

1. Lu T, Schubert C, Cummings MD, Bignan G, Connolly PJ, Smans K, Ludovici D, Parker MH, Meyer C, Rocaboy C, Alexander R, Grasberger B, De Breucker S, Esser N, Fraiponts E, Gilissen R, Janssens B, Peeters D, Van Nuffel L, Vermeulen P, Bischoff J, Meerpoel L..  (2018)  Design and synthesis of a series of bioavailable fatty acid synthase (FASN) KR domain inhibitors for cancer therapy.,  28  (12): [PMID:29779975] [10.1016/j.bmcl.2018.05.014]

Source

Source(1):

• Scientific Literature