N-[2-Chloro-4-({7-methyl-5-oxo-8-[meso-3,4,5-trimethylpiperazin-1-yl]-1,5-dihydro-2H-chromeno[3,4-c]pyridin-3(4H)-yl}carbonyl)phenyl]methanesulfonamide

ID: ALA4584730

PubChem CID: 134560537

Max Phase: Preclinical

Molecular Formula: C28H33ClN4O5S

Molecular Weight: 573.12

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1c(N2C[C@@H](C)N(C)[C@@H](C)C2)ccc2c3c(c(=O)oc12)CN(C(=O)c1ccc(NS(C)(=O)=O)c(Cl)c1)CC3

Standard InChI:  InChI=1S/C28H33ClN4O5S/c1-16-13-33(14-17(2)31(16)4)25-9-7-21-20-10-11-32(15-22(20)28(35)38-26(21)18(25)3)27(34)19-6-8-24(23(29)12-19)30-39(5,36)37/h6-9,12,16-17,30H,10-11,13-15H2,1-5H3/t16-,17+

Standard InChI Key:  CKHTVWRHUUKZSV-CALCHBBNSA-N

Molfile:  

 
     RDKit          2D

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   28.0276  -14.8437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7353  -15.2553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7353  -16.0744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0276  -16.4819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3157  -16.0744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6080  -16.4846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6110  -17.3030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3149  -17.7094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0268  -17.2974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9029  -17.7106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   24.4827  -18.5300    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4826  -17.7106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1907  -17.3030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7746  -17.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7746  -18.9418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   30.1509  -15.2554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.4431  -14.8437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8631  -14.8436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8631  -14.0282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5712  -15.2554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2795  -14.8438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9881  -15.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9881  -16.0746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2820  -16.4813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5712  -16.0757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2820  -17.3007    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   33.6962  -16.4823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.4042  -16.0746    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   35.1123  -16.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8171  -15.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   28.0276  -14.0284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  4  3  2  0
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  6  5  2  0
  1  6  1  0
  6  7  1  0
  7  8  2  0
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  8 11  1  0
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 11 16  1  0
 15 17  1  1
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  7 20  1  0
  4 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
  3 24  1  0
 23 25  1  0
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 32 31  2  0
 27 32  1  0
 31 33  1  0
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 34 35  1  0
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 35 38  2  0
  2 39  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4584730

   ---

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: 573.12

Molecular Weight (Monoisotopic): 572.1860

AlogP: 3.85

#Rotatable Bonds: 4

Polar Surface Area: 103.17

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.01

CX Basic pKa: 8.13

CX LogP: 2.45

CX LogD: 1.92

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.47

Np Likeness Score: -1.20

References

1. Kawai J, Toki T, Ota M, Inoue H, Takata Y, Asahi T, Suzuki M, Shimada T, Ono K, Suzuki K, Takaishi S, Ohki H, Matsui S, Tsutsumi S, Hirota Y, Nakayama K..  (2019)  Discovery of a Potent, Selective, and Orally Available MTHFD2 Inhibitor (DS18561882) with in Vivo Antitumor Activity.,  62  (22): [PMID:31638799] [10.1021/acs.jmedchem.9b01113]

Source

Source(1):

• Scientific Literature