(S)-1-(11,15-dimethoxy-3-methyl-13-oxa-3-azahexacyclo[13.2.2.12,8.01,6.06,14.07,12]icosa-7,9,11,18-tetraen-16-yl)ethyl isothiocyanate

ID: ALA3038195

PubChem CID: 73346684

Max Phase: Preclinical

Molecular Formula: C24H28N2O3S

Molecular Weight: 424.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c3c1O[C@@H]1[C@]34CCN(C)[C@H](C2)[C@]42C=C[C@@]1(OC)C([C@H](C)N=C=S)C2

Standard InChI:  InChI=1S/C24H28N2O3S/c1-14(25-13-30)16-12-22-7-8-24(16,28-4)21-23(22)9-10-26(2)18(22)11-15-5-6-17(27-3)20(29-21)19(15)23/h5-8,14,16,18,21H,9-12H2,1-4H3/t14-,16?,18+,21+,22+,23-,24+/m0/s1

Standard InChI Key:  XVYDBKXHAQVZDF-MBOWOLJHSA-N

Molfile:  

     RDKit          2D

 32 37  0  0  1  0  0  0  0  0999 V2000
    2.7223   -1.8956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4321   -2.3173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0084   -2.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9916   -3.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7223   -1.0772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0084   -0.6681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6033   -1.4906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1503   -1.9081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6973   -3.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4363   -0.6681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6931   -2.3048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6931   -3.0355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4238   -3.1357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1503   -1.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8601   -2.3215    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2526   -5.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3068   -1.3027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0084    0.1628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9708   -4.7724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5386   -5.5866    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.7265   -1.3027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4363    0.1628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6931   -4.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2693   -3.5198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7223    0.5762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2902    0.5762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5740   -2.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5198   -4.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5637   -3.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2902    1.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5628   -2.6226    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2038   -2.4786    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  3  1  0
  5  1  1  0
  6  5  1  0
  7  3  1  0
  8  2  1  0
  9  4  1  0
 10  5  2  0
  2 11  1  6
  4 12  1  0
 13  2  1  0
 14 10  1  0
 15 21  1  0
 16 19  2  0
  1 17  1  1
 18  6  2  0
 23 19  1  0
 20 16  2  0
 21 17  1  0
 22 10  1  0
 23  9  1  0
  4 24  1  6
 25 22  2  0
 26 18  1  0
 27 15  1  0
 23 28  1  6
 29 24  1  0
 30 26  1  0
  6  7  1  0
 13  9  1  0
 15  8  1  0
 14  8  1  0
 12 11  2  0
 25 18  1  0
  8 31  1  6
  3 32  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA3038195

   (1R,2S,6R,14R,15R)-19-[(1S)-1-isothiocyanatoethyl]-11,15-dimethoxy-5-methyl-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11,16-tetraene

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: 424.57

Molecular Weight (Monoisotopic): 424.1821

AlogP: 3.41

#Rotatable Bonds: 4

Polar Surface Area: 43.29

Molecular Species: BASE

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.11

CX LogP: 3.23

CX LogD: 1.52

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.42

Np Likeness Score: 1.53

References

1. Klein P, Nelson WL, Yao YH, Simon EJ..  (1990)  Electrophilic alpha-methylene-gamma-lactone and isothiocyanate opioid ligands related to etorphine.,  33  (8): [PMID:2165166] [10.1021/jm00170a038]

Source

Source(1):

• Scientific Literature