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

ID: ALA5094437

PubChem CID: 166634143

Max Phase: Preclinical

Molecular Formula: C26H28N4O

Molecular Weight: 412.54

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1nc(N2C[C@H](Cc3ccccc3)C[C@H]2CO)c2c(n1)[nH]c1c(C3CC3)cccc12

Standard InChI:  InChI=1S/C26H28N4O/c1-16-27-25-23(22-9-5-8-21(19-10-11-19)24(22)29-25)26(28-16)30-14-18(13-20(30)15-31)12-17-6-3-2-4-7-17/h2-9,18-20,31H,10-15H2,1H3,(H,27,28,29)/t18-,20+/m1/s1

Standard InChI Key:  HLTNLSHVMKDQCW-QUCCMNQESA-N

Molfile:  

 
     RDKit          2D

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   13.4037   -9.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8601   -9.0443    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9949   -9.9879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.2031   -9.4782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6959   -8.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.0951  -12.6916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5782  -12.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3954  -12.0359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8010  -12.7453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6532  -12.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9084  -12.5757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8290  -11.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0851  -11.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4204  -11.9019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5045  -12.7190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2486  -13.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1 21  1  0
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  5 19  1  0
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  1 25  1  1
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 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5094437

   ---

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: 412.54

Molecular Weight (Monoisotopic): 412.2263

AlogP: 4.73

#Rotatable Bonds: 5

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: 7.57

CX LogP: 5.41

CX LogD: 5.01

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.50

Np Likeness Score: -0.18

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