(4-bromophenyl)(1,9-dihydroxy-2,10-dimethoxy-6a,7-dihydro-4H-dibenzo[de,g]quinolin-6(5H)-yl)methanone

ID: ALA4850842

PubChem CID: 164615589

Max Phase: Preclinical

Molecular Formula: C25H22BrNO5

Molecular Weight: 496.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1O)CC1c3c(cc(OC)c(O)c3-2)CCN1C(=O)c1ccc(Br)cc1

Standard InChI:  InChI=1S/C25H22BrNO5/c1-31-20-12-17-15(10-19(20)28)9-18-22-14(11-21(32-2)24(29)23(17)22)7-8-27(18)25(30)13-3-5-16(26)6-4-13/h3-6,10-12,18,28-29H,7-9H2,1-2H3

Standard InChI Key:  DENLKMJONYJIOY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
    4.2084  -12.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2072  -13.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9135  -12.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6221  -12.7784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0390  -13.6010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0402  -12.7804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3294  -12.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6209  -13.5990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157  -14.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3231  -14.8177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3255  -14.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6179  -15.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9194  -14.8151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2182  -15.2155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2141  -16.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9172  -16.4317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6156  -16.0290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5003  -14.0116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5005  -12.3736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5004  -11.5564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9165  -17.2489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5051  -16.4310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7987  -16.0202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7441  -14.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7388  -14.8314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4544  -13.6102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1557  -14.0265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8656  -13.6231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8713  -12.8051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1613  -12.3920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4543  -12.7978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5811  -12.4001    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  9  1  0
  4  3  2  0
  3  1  1  0
  4  8  1  0
  4  7  1  0
 11  5  1  0
  5  6  1  0
  6  7  1  0
  8  9  2  0
  8 11  1  0
  9 13  1  0
 12 10  1  0
 10 11  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
  2 18  1  0
  1 19  1  0
 19 20  1  0
 16 21  1  0
 15 22  1  0
 22 23  1  0
  5 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4850842

   ---

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: 496.36

Molecular Weight (Monoisotopic): 495.0681

AlogP: 4.84

#Rotatable Bonds: 3

Polar Surface Area: 79.23

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.30

CX Basic pKa: ┄

CX LogP: 4.63

CX LogD: 4.62

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.54

Np Likeness Score: 0.64

References

1. Chang L, Zhang Q, Tang Y, Fang Y, Dou R, Chu Y, Xia Y, Wei Z, Chen L, Dai Y..  (2021)  Synthesis of norisoboldine derivatives and bioactivity assay for inducing the generation of regulatory T cells.,  37  [PMID:33556569] [10.1016/j.bmcl.2021.127844]

Source

Source(1):

• Scientific Literature