4-cyclopropylmethyl-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7,9,11(18)-trien-14-yl 2-methylacrylate

ID: ALA3084322

PubChem CID: 76335129

Max Phase: Preclinical

Molecular Formula: C24H29NO5

Molecular Weight: 411.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C)C(=O)O[C@H]1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5c4[C@@]2(CCN3CC2CC2)[C@H]1O5

Standard InChI:  InChI=1S/C24H29NO5/c1-13(2)22(27)29-17-7-8-24(28)18-11-15-5-6-16(26)20-19(15)23(24,21(17)30-20)9-10-25(18)12-14-3-4-14/h5-6,14,17-18,21,26,28H,1,3-4,7-12H2,2H3/t17-,18+,21-,23-,24+/m0/s1

Standard InChI Key:  XYCPEHAPRMZWKX-WSEOTULYSA-N

Molfile:  

     RDKit          2D

 31 36  0  0  1  0  0  0  0  0999 V2000
    0.1543   -1.2803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5755   -0.8299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1376   -2.0684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1802   -1.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8507   -2.4813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4637   -1.9308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2886   -1.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2977   -1.5805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5755   -2.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0400   -0.6547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2886   -2.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5305   -0.4546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3186   -0.2419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5254   -1.2678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5922   -0.7506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7531   -0.2419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1234   -1.5388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8507   -3.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5763   -1.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4987   -0.8049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4612    0.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1910   -0.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5755   -3.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9050   -0.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0317   -1.4804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6130   -0.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1376   -3.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7531    0.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5680   -3.7323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4662   -0.6547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0039   -1.2018    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  1  0
  5  3  2  0
  6  4  1  0
  7  2  1  0
 19  8  1  0
  9  3  1  0
 10 13  1  0
 11  9  1  0
 12  4  1  0
 12 13  1  6
  1 14  1  1
 15  2  1  0
 16 10  1  0
 17  8  1  0
 18  5  1  0
 14 19  1  0
 20 17  1  0
 21 20  1  0
 22 20  1  0
 23  9  2  0
 24 12  1  0
 25 10  2  0
  2 26  1  1
 27 23  1  0
 28 16  2  0
 29 18  1  0
 30 16  1  0
  5  6  1  0
  7  8  1  1
 24 15  1  0
  7 11  1  0
 18 27  2  0
 21 22  1  0
  4 31  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA3084322

   [(4R,4aS,7S,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl] 2-methylprop-2-enoate

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: 411.50

Molecular Weight (Monoisotopic): 411.2046

AlogP: 2.44

#Rotatable Bonds: 4

Polar Surface Area: 79.23

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.26

CX Basic pKa: 9.45

CX LogP: 2.66

CX LogD: 0.89

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.59

Np Likeness Score: 1.94

References

1. Olsen LD, Klein P, Nelson WL, Yao YH, Simon EJ..  (1990)  Conjugate addition ligands of opioid antagonists. Methacrylate esters and ethers of 6 alpha- and 6 beta-naltrexol.,  33  (2): [PMID:2153826] [10.1021/jm00164a043]

Source

Source(1):

• Scientific Literature