(S)-19-(1-isothiocyanatoethyl)-15-methoxy-3-methyl-13-oxa-3-azahexacyclo[13.2.2.12,8.01,6.06,14.07,12]icosa-7,9,11,16-tetraen-11-ol

ID: ALA3038197

PubChem CID: 73346685

Max Phase: Preclinical

Molecular Formula: C23H26N2O3S

Molecular Weight: 410.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@]12C=C[C@@]3(CC1[C@H](C)N=C=S)[C@H]1Cc4ccc(O)c5c4[C@@]3(CCN1C)[C@H]2O5

Standard InChI:  InChI=1S/C23H26N2O3S/c1-13(24-12-29)15-11-21-6-7-23(15,27-3)20-22(21)8-9-25(2)17(21)10-14-4-5-16(26)19(28-20)18(14)22/h4-7,13,15,17,20,26H,8-11H2,1-3H3/t13-,15?,17+,20+,21+,22-,23+/m0/s1

Standard InChI Key:  WTVMVUJOBOGEOT-MOEIEMDKSA-N

Molfile:  

     RDKit          2D

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    2.2839   -2.8726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9937   -3.2985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5699   -3.2735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5532   -4.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2839   -2.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5699   -1.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1649   -2.4718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7119   -2.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2589   -4.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9979   -1.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2589   -3.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2547   -4.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9854   -4.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7119   -2.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4259   -3.3068    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8184   -6.1627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5699   -0.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5324   -5.7536    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1002   -6.5678    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2881   -2.2839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9979   -0.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2589   -5.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8309   -4.5010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2839   -0.4050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8518   -0.4008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1356   -3.7202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9686   -5.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1253   -4.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9254   -3.6821    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7730   -3.0600    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
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 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
  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 30  1  6
  3 31  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA3038197

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

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: 410.54

Molecular Weight (Monoisotopic): 410.1664

AlogP: 3.10

#Rotatable Bonds: 3

Polar Surface Area: 54.29

Molecular Species: BASE

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.22

CX Basic pKa: 9.06

CX LogP: 2.80

CX LogD: 1.37

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.47

Np Likeness Score: 1.77

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