(R)-(3-(3-Aminopyrrolidin-1-carbonyl))-4,11-dihydroxy-2-methylnaphtho[2,3-f]indole-5,10-dione

ID: ALA4788897

PubChem CID: 162670138

Max Phase: Preclinical

Molecular Formula: C22H19N3O5

Molecular Weight: 405.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1[nH]c2c(O)c3c(c(O)c2c1C(=O)N1CC[C@@H](N)C1)C(=O)c1ccccc1C3=O

Standard InChI:  InChI=1S/C22H19N3O5/c1-9-13(22(30)25-7-6-10(23)8-25)14-17(24-9)21(29)16-15(20(14)28)18(26)11-4-2-3-5-12(11)19(16)27/h2-5,10,24,28-29H,6-8,23H2,1H3/t10-/m1/s1

Standard InChI Key:  WAQPMWBELPXNNM-SNVBAGLBSA-N

Molfile:  

 
     RDKit          2D

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   26.7513   -2.5960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7501   -3.4155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4582   -3.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4564   -2.1871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1650   -2.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1638   -3.4176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8739   -3.8289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8763   -2.1785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5909   -2.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5897   -3.4155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2990   -3.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2974   -2.1849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0073   -2.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0077   -3.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7894   -3.6665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.2722   -3.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7888   -2.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8763   -1.3613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8734   -4.6461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.2951   -1.3677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3003   -4.6426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.0409   -1.5595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8402   -1.3892    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.4939   -0.9525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.4433   -1.9342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1508   -1.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9805   -0.7259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1678   -0.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8975   -1.8573    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.0894   -3.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5  8  1  0
  6  7  1  0
  7 10  1  0
  9  8  1  0
  9 10  2  0
 10 11  1  0
 11 14  2  0
 13 12  2  0
 12  9  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 13  1  0
  8 18  2  0
  7 19  2  0
 12 20  1  0
 11 21  1  0
 17 22  1  0
 22 23  1  0
 22 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 23  1  0
 26 29  1  1
 16 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4788897

   ---

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: 405.41

Molecular Weight (Monoisotopic): 405.1325

AlogP: 1.84

#Rotatable Bonds: 1

Polar Surface Area: 136.72

Molecular Species: BASE

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.65

CX Basic pKa: 9.00

CX LogP: 1.43

CX LogD: 1.17

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.36

Np Likeness Score: -0.14

References

1. Tikhomirov AS,Litvinova VA,Andreeva DV,Tsvetkov VB,Dezhenkova LG,Volodina YL,Kaluzhny DN,Treshalin ID,Schols D,Ramonova AA,Moisenovich MM,Shtil AA,Shchekotikhin AE.  (2020)  Amides of pyrrole- and thiophene-fused anthraquinone derivatives: A role of the heterocyclic core in antitumor properties.,  199  [PMID:32428792] [10.1016/j.ejmech.2020.112294]

Source

Source(1):

• Scientific Literature