Rhopaladin B

ID: ALA3809172

PubChem CID: 135464244

Max Phase: Preclinical

Molecular Formula: C21H14N4O3

Molecular Weight: 370.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1N=C(C(=O)c2c[nH]c3ccccc23)N/C1=C\c1c[nH]c2cc(O)ccc12

Standard InChI:  InChI=1S/C21H14N4O3/c26-12-5-6-13-11(9-22-17(13)8-12)7-18-21(28)25-20(24-18)19(27)15-10-23-16-4-2-1-3-14(15)16/h1-10,22-23,26H,(H,24,25,28)/b18-7-

Standard InChI Key:  DOCOAQYXWJFYRB-WSVATBPTSA-N

Molfile:  

     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
    3.6500    2.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2449    4.2986    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7359    4.1352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0412    2.6666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7388    1.9224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5429    5.0233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1812    2.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3808    3.5211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4059    2.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0322   -1.7765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4410   -0.3950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5540    0.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8414   -0.1781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2705    0.2906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3872   -0.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0650   -2.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6181   -2.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5191   -1.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9522   -3.0080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  1  5  1  0
  3  6  2  0
  7  8  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
  9 17  1  0
 12 17  2  0
  7 11  1  0
  1  7  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 19 27  1  0
 22 27  2  0
 25 28  1  0
 18 21  1  0
  4 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3809172

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 370.37

Molecular Weight (Monoisotopic): 370.1066

AlogP: 3.11

#Rotatable Bonds: 3

Polar Surface Area: 110.34

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.52

CX Basic pKa: ┄

CX LogP: 2.29

CX LogD: 2.29

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.33

Np Likeness Score: 0.23

References

1. Tantak MP, Gupta V, Nikhil K, Arun V, Singh RP, Jha PN, Shah K, Kumar D..  (2016)  Sequential one-pot synthesis of bis(indolyl)glyoxylamides: Evaluation of antibacterial and anticancer activities.,  26  (13): [PMID:27173802] [10.1016/j.bmcl.2016.04.080]

2. Tantak MP, Klingler L, Arun V, Kumar A, Sadana R, Kumar D..  (2017)  Design and synthesis of bis(indolyl)ketohydrazide-hydrazones: Identification of potent and selective novel tubulin inhibitors.,  136  [PMID:28494255] [10.1016/j.ejmech.2017.04.078]

Source

Source(1):

• Scientific Literature