3-((3R,4R)-3,4-Diaminopyrrolidin-1-carbonyl)-4,11-dihydroxy-2-methyl-1H-naphtho[2,3-f]indole-5,10-dione

ID: ALA4792180

PubChem CID: 162670590

Max Phase: Preclinical

Molecular Formula: C22H20N4O5

Molecular Weight: 420.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1[nH]c2c(O)c3c(c(O)c2c1C(=O)N1C[C@@H](N)[C@H](N)C1)C(=O)c1ccccc1C3=O

Standard InChI:  InChI=1S/C22H20N4O5/c1-8-13(22(31)26-6-11(23)12(24)7-26)14-17(25-8)21(30)16-15(20(14)29)18(27)9-4-2-3-5-10(9)19(16)28/h2-5,11-12,25,29-30H,6-7,23-24H2,1H3/t11-,12-/m1/s1

Standard InChI Key:  MBZKGALYKMBSMJ-VXGBXAGGSA-N

Molfile:  

 
     RDKit          2D

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    1.8641   -3.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8629   -4.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5710   -4.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5692   -3.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2778   -3.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2766   -4.2926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9867   -4.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9891   -3.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7038   -3.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7025   -4.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4118   -4.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4103   -3.0599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1201   -3.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1205   -4.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9022   -4.5414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3850   -3.8763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9016   -3.2118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9891   -2.2363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9862   -5.5211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4079   -2.2427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4131   -5.5175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1538   -2.4345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9530   -2.2642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6067   -1.8275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5561   -2.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2636   -2.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0933   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2806   -1.5160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0103   -2.7322    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2022   -3.8759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6398   -0.9933    0.0000 N   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  6
 16 30  1  0
 27 31  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4792180

   ---

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: 420.43

Molecular Weight (Monoisotopic): 420.1434

AlogP: 0.77

#Rotatable Bonds: 1

Polar Surface Area: 162.74

Molecular Species: BASE

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.64

CX Basic pKa: 8.67

CX LogP: 0.70

CX LogD: 0.46

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.28

Np Likeness Score: 0.06

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