N-(3-chloro-1,4-dihydro-1,4-dioxo-2-naphthalenyl)-L-tryptophan

ID: ALA5204726

Cas Number: 185351-23-9

PubChem CID: 1427125

Max Phase: Preclinical

Molecular Formula: C21H15ClN2O4

Molecular Weight: 394.81

Names and Identifiers

Canonical SMILES:  O=C1C(Cl)=C(N[C@@H](Cc2c[nH]c3ccccc23)C(=O)O)C(=O)c2ccccc21

Standard InChI:  InChI=1S/C21H15ClN2O4/c22-17-18(20(26)14-7-2-1-6-13(14)19(17)25)24-16(21(27)28)9-11-10-23-15-8-4-3-5-12(11)15/h1-8,10,16,23-24H,9H2,(H,27,28)/t16-/m0/s1

Standard InChI Key:  ZKNQSBBALRSDBQ-INIZCTEOSA-N

Molfile:  

 
     RDKit          2D

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   -2.4377    1.6054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7258    1.1936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7258    0.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4359   -0.0433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1523    0.3647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0112    1.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2967    1.1935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2967    0.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0112   -0.0441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0112    2.4312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0112   -0.8692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4178    1.6060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4178   -0.0441    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1324    1.1935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8470    1.6060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1324    0.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8470    2.4312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5616    1.1935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8470   -0.0441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6004    0.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1523   -0.3216    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7399   -1.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9332   -0.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9934   -1.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4416   -2.4312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6385   -2.2623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3791   -1.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  3  7  1  0
  8  7  1  0
  9  8  2  0
 10  9  1  0
  4 10  1  0
  7 11  2  0
 10 12  2  0
  8 13  1  0
  9 14  1  0
 13 15  1  0
 15 16  1  6
 15 17  1  0
 16 18  2  0
 16 19  1  0
 17 20  1  0
 21 20  2  0
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 23 24  2  0
 24 20  1  0
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 26 25  2  0
 27 26  1  0
 28 27  2  0
 24 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5204726

   Cl-NQTrp

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 394.81

Molecular Weight (Monoisotopic): 394.0720

AlogP: 3.28

#Rotatable Bonds: 5

Polar Surface Area: 99.26

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.88

CX Basic pKa: ┄

CX LogP: 2.96

CX LogD: -0.26

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.62

Np Likeness Score: -0.03

References

1. Wang L, Bharti, Kumar R, Pavlov PF, Winblad B..  (2021)  Small molecule therapeutics for tauopathy in Alzheimer's disease: Walking on the path of most resistance.,  209  [PMID:33139110] [10.1016/j.ejmech.2020.112915]

Source

Source(1):

• Scientific Literature