(S)-(1-(8-cyclopropyl-2-methyl-9H-pyrimido[4,5-b]indol-4-yl)pyrrolidin-2-yl)methanol

ID: ALA5094187

PubChem CID: 166633820

Max Phase: Preclinical

Molecular Formula: C19H22N4O

Molecular Weight: 322.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1nc(N2CCC[C@H]2CO)c2c(n1)[nH]c1c(C3CC3)cccc12

Standard InChI:  InChI=1S/C19H22N4O/c1-11-20-18-16(19(21-11)23-9-3-4-13(23)10-24)15-6-2-5-14(12-7-8-12)17(15)22-18/h2,5-6,12-13,24H,3-4,7-10H2,1H3,(H,20,21,22)/t13-/m0/s1

Standard InChI Key:  KSJZZGFTBGBHFN-ZDUSSCGKSA-N

Molfile:  

 
     RDKit          2D

 24 28  0  0  0  0  0  0  0  0999 V2000
    4.1107  -12.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1974   -8.4484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8603   -8.9306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6041   -9.7047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1460  -10.3116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9441  -10.1456    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1975   -9.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6540   -8.7636    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7888   -9.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5390   -8.9316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7439   -8.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1978   -9.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4523  -10.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2468  -10.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9969   -9.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4897   -7.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6608   -7.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8832   -7.4398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946  -11.0886    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1163  -11.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8890  -12.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3720  -11.7518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1892  -11.7552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5948  -12.4646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  4  1  0
  3  2  1  0
  2 10  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  7 15  1  0
 17 16  1  0
 18 17  1  0
 16 18  1  0
 11 16  1  0
 19 20  1  0
 20  1  1  0
  1 21  1  0
 21 22  1  0
 22 19  1  0
  5 19  1  0
 22 23  1  6
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5094187

   ---

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: 322.41

Molecular Weight (Monoisotopic): 322.1794

AlogP: 3.26

#Rotatable Bonds: 3

Polar Surface Area: 65.04

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.22

CX Basic pKa: 7.58

CX LogP: 3.45

CX LogD: 3.05

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.78

Np Likeness Score: -0.38

References

1. Bessho Y, Akaki T, Hara Y, Yamakawa M, Obika S, Mori G, Ubukata M, Yasue K, Nakane Y, Terasako Y, Orita T, Doi S, Iwanaga T, Fujishima A, Adachi T, Ueno H, Motomura T..  (2021)  Structure-based drug design of novel and highly potent pyruvate dehydrogenase kinase inhibitors.,  52  [PMID:34808405] [10.1016/j.bmc.2021.116514]

Source

Source(1):

• Scientific Literature