(5aR,6R)-8-fluoro-6-hydroxy-5a,6-dihydroindolo[2,1-b]quinazolin-12(5H)-one

ID: ALA3087012

PubChem CID: 76320783

Max Phase: Preclinical

Molecular Formula: C15H11FN2O2

Molecular Weight: 270.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1c2ccccc2N[C@H]2[C@H](O)c3cc(F)ccc3N12

Standard InChI:  InChI=1S/C15H11FN2O2/c16-8-5-6-12-10(7-8)13(19)14-17-11-4-2-1-3-9(11)15(20)18(12)14/h1-7,13-14,17,19H/t13-,14-/m1/s1

Standard InChI Key:  BDLZXBGLTVZJBC-ZIAGYGMSSA-N

Molfile:  

     RDKit          2D

 21 24  0  0  0  0  0  0  0  0999 V2000
    4.1918   -9.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1907  -10.1347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9029  -10.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9011   -8.9104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6056   -9.3156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6085  -10.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3106  -10.5412    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3129   -8.9082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0237   -9.3176    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0245  -10.1360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7988  -10.3881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7975   -9.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2792   -9.7283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0959   -9.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4320   -8.9003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9536   -8.2318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1386   -8.3152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3129   -8.0910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0500  -11.1644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0204  -10.9454    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2487   -8.8183    0.0000 F   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  1  0
 10 11  1  0
 11 13  1  0
 12  9  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
  8 18  2  0
 11 19  1  1
 10 20  1  1
 15 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3087012

   (5aR,6R)-8-fluoro-6-hydroxy-5a,6-dihydro-5H-indolo[2,1-b]quinazolin-12-one

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: 270.26

Molecular Weight (Monoisotopic): 270.0805

AlogP: 2.27

#Rotatable Bonds: ┄

Polar Surface Area: 52.57

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.82

CX Basic pKa: ┄

CX LogP: 2.47

CX LogD: 2.47

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.77

Np Likeness Score: -0.44

References

1. Yang S, Li X, Hu F, Li Y, Yang Y, Yan J, Kuang C, Yang Q..  (2013)  Discovery of tryptanthrin derivatives as potent inhibitors of indoleamine 2,3-dioxygenase with therapeutic activity in Lewis lung cancer (LLC) tumor-bearing mice.,  56  (21): [PMID:24099220] [10.1021/jm401195n]

Source

Source(1):

• Scientific Literature