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

ID: ALA4130300

PubChem CID: 117992981

Max Phase: Preclinical

Molecular Formula: C28H29N5O2

Molecular Weight: 467.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1ncc2cc(-c3ccc(C4=NC5(CC5)C(=O)N4C[C@H]4CCN(C(=O)C5CC5)C4)cc3)ccc21

Standard InChI:  InChI=1S/C28H29N5O2/c1-31-24-9-8-22(14-23(24)15-29-31)19-2-4-20(5-3-19)25-30-28(11-12-28)27(35)33(25)17-18-10-13-32(16-18)26(34)21-6-7-21/h2-5,8-9,14-15,18,21H,6-7,10-13,16-17H2,1H3/t18-/m0/s1

Standard InChI Key:  KYFZEWZCYBWMGN-SFHVURJKSA-N

Molfile:  

     RDKit          2D

 35 41  0  0  0  0  0  0  0  0999 V2000
   13.2525   -5.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6694   -4.7133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8477   -4.7087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6220   -4.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4415   -4.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6184   -3.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2111   -4.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3945   -4.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9844   -3.5776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1638   -3.5797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7524   -4.2933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1716   -5.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9908   -4.9965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4411   -3.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8517   -4.2811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6517   -4.1038    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7330   -3.2892    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9832   -2.9616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2657   -4.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9311   -4.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4453   -3.6365    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6692   -3.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4510   -4.9627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6984   -2.8540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5011   -2.6805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1136   -3.2204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8194   -2.8086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6459   -2.0059    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8287   -1.9243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1940   -1.3919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9982   -1.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9379   -0.6118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6109   -2.1019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7771   -1.2977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0029   -3.4094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  1  3  1  0
  4  5  2  0
  5 15  1  0
 14  6  1  0
  6  7  2  0
  7  4  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  7  8  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 14  1  0
 16 19  1  0
 11 20  1  0
 20 21  1  0
 21 22  1  0
 22  2  1  0
  2 23  1  0
 23 20  2  0
 21 24  1  0
 25 24  1  6
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 25  1  0
 28 30  1  0
 30 31  1  0
 30 32  2  0
 33 31  1  0
 34 33  1  0
 31 34  1  0
 22 35  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4130300

   6-[[(3S)-1-(cyclopropanecarbonyl)pyrrolidin-3-yl]methyl]-5-[4-(1-methylindazol-5-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: 467.57

Molecular Weight (Monoisotopic): 467.2321

AlogP: 3.62

#Rotatable Bonds: 5

Polar Surface Area: 70.80

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.53

CX LogP: 2.85

CX LogD: 2.85

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.58

Np Likeness Score: -1.10

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