(3aR,10R)-2-Butyl-10-(3-hydroxy-phenyl)-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenta[b]fluorene-1,3-dione

ID: ALA4089675

PubChem CID: 49772558

Max Phase: Preclinical

Molecular Formula: C23H23N3O3

Molecular Weight: 389.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCN1C(=O)[C@H]2Cc3c([nH]c4ccccc34)[C@@H](c3cccc(O)c3)N2C1=O

Standard InChI:  InChI=1S/C23H23N3O3/c1-2-3-11-25-22(28)19-13-17-16-9-4-5-10-18(16)24-20(17)21(26(19)23(25)29)14-7-6-8-15(27)12-14/h4-10,12,19,21,24,27H,2-3,11,13H2,1H3/t19-,21-/m1/s1

Standard InChI Key:  IDGCPAFIELNTPI-TZIWHRDSSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
    7.8329   -6.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2025   -6.1717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3572   -6.9878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6767   -5.5040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4868   -5.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5448   -6.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8533   -7.6486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6203   -6.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6293   -7.3840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3479   -7.7873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3258   -6.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3592   -8.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6548   -9.0169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6643   -9.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3774  -10.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0825   -9.8126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0695   -8.9977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0449   -6.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0565   -7.3615    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8443   -7.6053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3195   -6.9313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8254   -6.2712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0670   -5.4905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1367   -6.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5352   -6.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3523   -6.1948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7508   -5.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0374   -5.7162    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7964  -10.2102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1077   -8.3788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0
  7  9  1  0
  5  4  1  0
  3  7  1  0
  1  3  1  0
  1  5  2  0
  8  1  1  0
  6  3  2  0
  2  6  1  0
  8  9  2  0
  9 10  1  0
 10 19  1  0
 18 11  1  0
 11  8  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 10 12  1  6
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
 22 23  2  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 18 28  1  1
 16 29  1  0
 20 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4089675

   (10R,15R)-13-butyl-10-(3-hydroxyphenyl)-8,11,13-triazatetracyclo[7.7.0.02,7.011,15]hexadeca-1(9),2,4,6-tetraene-12,14-dione

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: 389.46

Molecular Weight (Monoisotopic): 389.1739

AlogP: 3.95

#Rotatable Bonds: 4

Polar Surface Area: 76.64

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.38

CX Basic pKa: ┄

CX LogP: 3.80

CX LogD: 3.79

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.66

Np Likeness Score: -0.25

References

1. Samundeeswari S, Chougala B, Holiyachi M, Shastri L, Kulkarni M, Dodamani S, Jalalpur S, Joshi S, Dixit S, Sunagar V, Hunnur R..  (2017)  Design and synthesis of novel phenyl -1, 4-beta-carboline-hybrid molecules as potential anticancer agents.,  128  [PMID:28171832] [10.1016/j.ejmech.2017.01.014]

Source

Source(1):

• Scientific Literature