(R)-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: ALA2021335

PubChem CID: 70683393

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)C1Cc4ccc(O)c5c4C3(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-/m1/s1

Standard InChI Key:  WTVMVUJOBOGEOT-UCYOIAKYSA-N

Molfile:  

     RDKit          2D

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   -4.3268    7.7902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6393    9.8569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0185    4.1277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3643    6.1902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6193    3.9979    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8937    6.7687    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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  3 31  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA2021335

   (1R,14R,15R)-19-[(1R)-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