4-cyclopropylmethyl-14-(2-isothiocyanatoethoxy)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-triene-10,17-diol

ID: ALA2310843

PubChem CID: 71719111

Max Phase: Preclinical

Molecular Formula: C22H28N2O4S

Molecular Weight: 416.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1ccc2c3c1O[C@H]1[C@H](OCCN=S)CC[C@@]4(O)[C@@H](C2)N(CC2CC2)CC[C@]314

Standard InChI:  InChI=1S/C22H28N2O4S/c25-15-4-3-14-11-17-22(26)6-5-16(27-10-8-23-29)20-21(22,18(14)19(15)28-20)7-9-24(17)12-13-1-2-13/h3-4,13,16-17,20,25-26H,1-2,5-12H2/t16-,17-,20+,21+,22-/m1/s1

Standard InChI Key:  JWJRPPUYZVLUJO-KXIGMZGYSA-N

Molfile:  

     RDKit          2D

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   -4.1545   -4.4712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7420   -3.7568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9170   -3.7567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5045   -4.4712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3014   -3.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8500   -1.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4375   -1.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2624   -1.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3920   -6.6147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4419   -6.6145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0294   -7.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7956   -7.3290    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6206   -7.3290    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2982   -6.8786    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4171   -2.8907    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
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  6 15  1  0
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  9 17  1  1
  8 18  1  0
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 10 20  1  1
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  5 25  1  0
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 27 28  1  0
 28 29  2  0
 14 30  1  1
  8 31  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA2310843

   (4R,4aS,7R,7aR,12bS)-3-(cyclopropylmethyl)-7-(2-thionitrosoethoxy)-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,9-diol

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: 416.54

Molecular Weight (Monoisotopic): 416.1770

AlogP: 2.07

#Rotatable Bonds: 6

Polar Surface Area: 74.52

Molecular Species: BASE

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.30

CX Basic pKa: 9.47

CX LogP: 2.16

CX LogD: 0.37

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.69

Np Likeness Score: 1.54

References

1. Dasher WE, Klein P, Nelson WL..  (1992)  Electrophilic opioid ligands. Oxygen tethered alpha-methylene-gamma-lactone, acrylate, isothiocyanate, and epoxide derivatives of 6 beta-naltrexol.,  35  (13): [PMID:1320121] [10.1021/jm00091a005]

Source

Source(1):

• Scientific Literature