(rac)-(1R,2S)-5'-methoxy-2-(3-(6-morpholinopyridin-3-yl)-1H-indazol-6-yl)spiro[cyclopropane-1,3'-indolin]-2'-one

ID: ALA4590185

PubChem CID: 58486131

Max Phase: Preclinical

Molecular Formula: C27H25N5O3

Molecular Weight: 467.53

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1)[C@]1(C[C@H]1c1ccc3c(-c4ccc(N5CCOCC5)nc4)n[nH]c3c1)C(=O)N2

Standard InChI:  InChI=1S/C27H25N5O3/c1-34-18-4-6-22-20(13-18)27(26(33)29-22)14-21(27)16-2-5-19-23(12-16)30-31-25(19)17-3-7-24(28-15-17)32-8-10-35-11-9-32/h2-7,12-13,15,21H,8-11,14H2,1H3,(H,29,33)(H,30,31)/t21-,27-/m0/s1

Standard InChI Key:  ZWOUJAABXJJBDH-IDISGSTGSA-N

Molfile:  

 
     RDKit          2D

 35 41  0  0  0  0  0  0  0  0999 V2000
    2.4202   -6.6057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6244   -6.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8383   -7.1886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8717   -6.7246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3279   -6.1058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7442   -5.3947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5547   -5.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1153   -4.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667   -4.1737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0521   -3.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4951   -4.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6915   -7.5296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1492   -6.2196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8450   -6.6603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9002   -5.0111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1745   -5.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6041   -5.4495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5760   -6.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3543   -6.5593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8635   -5.9064    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3997   -5.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6659   -4.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4764   -4.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7416   -3.5027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1974   -2.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3847   -3.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1232   -3.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4623   -2.1038    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2724   -1.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5373   -1.1661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9955   -0.5434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1853   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9169   -1.4866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4216   -3.5692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730   -2.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  1  3  1  0
  2  4  1  1
  2  7  1  0
  6  5  1  0
  5  4  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  4 12  2  0
  1 13  1  6
 13 14  2  0
 14 18  1  0
 17 15  1  0
 15 16  2  0
 16 13  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 17  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 21 22  1  0
 28 29  1  0
 28 33  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 25 28  1  0
 34 35  1  0
  9 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4590185

   (1R*,2S*)-5'-Methoxy-2-(3-(6-morpholinopyridin-3-yl)-1H-indazol-6-yl)spiro[cyclopropane-1,3'-indolin]-2'-one

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 467.53

Molecular Weight (Monoisotopic): 467.1957

AlogP: 3.85

#Rotatable Bonds: 4

Polar Surface Area: 92.37

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.38

CX Basic pKa: 5.37

CX LogP: 3.59

CX LogD: 3.59

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.47

Np Likeness Score: -0.69

References

1. Li SW, Liu Y, Sampson PB, Patel NK, Forrest BT, Edwards L, Laufer R, Feher M, Ban F, Awrey DE, Hodgson R, Beletskaya I, Mao G, Mason JM, Wei X, Luo X, Kiarash R, Green E, Mak TW, Pan G, Pauls HW..  (2016)  Design and optimization of (3-aryl-1H-indazol-6-yl)spiro[cyclopropane-1,3'-indolin]-2'-ones as potent PLK4 inhibitors with oral antitumor efficacy.,  26  (19): [PMID:27592744] [10.1016/j.bmcl.2016.08.063]

Source

Source(1):

• Scientific Literature