(S)-3-(3-Aminopyrrolidin-1-carbonyl)-4,11-dihydroxy-1,2-dimethyl-1H-naphtho[2,3-f]indole-5,10-dione

ID: ALA4776692

PubChem CID: 162643150

Max Phase: Preclinical

Molecular Formula: C23H21N3O5

Molecular Weight: 419.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1c(C(=O)N2CC[C@H](N)C2)c2c(O)c3c(c(O)c2n1C)C(=O)c1ccccc1C3=O

Standard InChI:  InChI=1S/C23H21N3O5/c1-10-14(23(31)26-8-7-11(24)9-26)15-18(25(10)2)22(30)17-16(21(15)29)19(27)12-5-3-4-6-13(12)20(17)28/h3-6,11,29-30H,7-9,24H2,1-2H3/t11-/m0/s1

Standard InChI Key:  SJXVHGYTJTYPSG-NSHDSACASA-N

Molfile:  

 
     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
    2.1654  -10.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1642  -11.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8723  -11.8024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705  -10.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5791  -10.5703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5779  -11.3955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2880  -11.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2904  -10.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0050  -10.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0038  -11.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7131  -11.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7115  -10.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4214  -10.5690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4218  -11.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2035  -11.6444    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6863  -10.9793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2029  -10.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2904   -9.3393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2875  -12.6240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7092   -9.3457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7144  -12.6205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4550   -9.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2543   -9.3672    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9080   -8.9304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5035  -10.9789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8604   -9.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5679   -9.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3976   -8.7005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5849   -8.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3146   -9.8318    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4563  -12.4215    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
 16 25  1  0
 23 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 23  1  0
 27 30  1  6
 15 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4776692

   ---

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: 419.44

Molecular Weight (Monoisotopic): 419.1481

AlogP: 1.85

#Rotatable Bonds: 1

Polar Surface Area: 125.86

Molecular Species: BASE

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.62

CX Basic pKa: 9.57

CX LogP: 1.65

CX LogD: 1.41

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.40

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