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

ID: ALA2021332

PubChem CID: 70696006

Max Phase: Preclinical

Molecular Formula: C26H30N2O3S

Molecular Weight: 450.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@]12C=C[C@@]3(CC1[C@@H](C)N=C=S)C1Cc4ccc(O)c5c4C3(CCN1CC1CC1)[C@H]2O5

Standard InChI:  InChI=1S/C26H30N2O3S/c1-15(27-14-32)18-12-24-7-8-26(18,30-2)23-25(24)9-10-28(13-16-3-4-16)20(24)11-17-5-6-19(29)22(31-23)21(17)25/h5-8,15-16,18,20,23,29H,3-4,9-13H2,1-2H3/t15-,18?,20?,23-,24-,25?,26-/m1/s1

Standard InChI Key:  OUKDLWAAMCMZEI-ACQAJGDTSA-N

Molfile:  

     RDKit          2D

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   -4.9368    2.4310    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2998    6.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7773    3.6524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1989    4.4945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7523    8.5842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1864    8.5842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9118    4.9156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0438    2.6886    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4406    5.4956    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
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  4 28  1  6
 29 26  2  0
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 32 28  1  0
 27 33  1  6
  6  7  1  0
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  9  8  1  0
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 13 12  2  0
 29 19  1  0
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  3 34  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA2021332

   (1R,14R,15R)-5-(cyclopropylmethyl)-19-[(1R)-1-isothiocyanatoethyl]-15-methoxy-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: 450.60

Molecular Weight (Monoisotopic): 450.1977

AlogP: 3.88

#Rotatable Bonds: 5

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: 10.39

CX Basic pKa: 9.59

CX LogP: 3.41

CX LogD: 1.50

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.42

Np Likeness Score: 1.42

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