(11S,19R)-15-(3-Bromobenzoyl)-11-ethyl-19-methoxy-8,15-diazatetracyclo-[9.6.2.0(2),7.0(8,18)]nonadeca-1(18),2,4,6-tetraen-9-one

ID: ALA4527708

PubChem CID: 155544367

Max Phase: Preclinical

Molecular Formula: C27H29BrN2O3

Molecular Weight: 509.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC[C@]12CCCN(C(=O)c3cccc(Br)c3)CCc3c(n(c4ccccc34)C(=O)C1)[C@@H]2OC

Standard InChI:  InChI=1S/C27H29BrN2O3/c1-3-27-13-7-14-29(26(32)18-8-6-9-19(28)16-18)15-12-21-20-10-4-5-11-22(20)30(23(31)17-27)24(21)25(27)33-2/h4-6,8-11,16,25H,3,7,12-15,17H2,1-2H3/t25-,27-/m0/s1

Standard InChI Key:  CHODJULWLMPNCK-BDYUSTAISA-N

Molfile:  

 
     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
   31.0547   -7.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0535   -8.0423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7595   -8.4466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7576   -6.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4730   -7.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4733   -8.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2494   -6.9585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7327   -7.6257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2540   -8.2889    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.5850   -9.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1153   -9.6769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.5535   -7.6263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9657   -8.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7910   -8.3416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1988   -9.0606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4092   -9.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5043   -6.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3102   -5.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5651   -5.2096    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.4362   -5.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9309   -6.0743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9252   -7.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0129   -4.5987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2655   -3.8111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2038   -4.7710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.0744   -3.6411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3271   -2.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7747   -2.2425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9620   -2.4182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7130   -3.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1355   -2.6869    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   34.9618   -6.9167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.8187   -6.1924    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
  6  9  1  0
  7  5  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
  8 12  1  0
 12 13  1  0
 13 14  1  6
 14 15  1  0
 13 16  1  0
 10 16  1  0
  7 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 13 22  1  0
 21 22  1  0
 19 23  1  0
 23 24  1  0
 23 25  2  0
 24 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 24  1  0
 27 31  1  0
 12 32  1  6
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4527708

   ---

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: 509.44

Molecular Weight (Monoisotopic): 508.1362

AlogP: 6.01

#Rotatable Bonds: 3

Polar Surface Area: 51.54

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.71

CX LogD: 4.71

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.43

Np Likeness Score: -0.11

References

1. Norwood VM, Brice-Tutt AC, Eans SO, Stacy HM, Shi G, Ratnayake R, Rocca JR, Abboud KA, Li C, Luesch H, McLaughlin JP, Huigens RW..  (2020)  Preventing Morphine-Seeking Behavior through the Re-Engineering of Vincamine's Biological Activity.,  63  (10): [PMID:31913038] [10.1021/acs.jmedchem.9b01924]

Source

Source(1):

• Scientific Literature