(E)-Methyl 2-((1'S,6'S,7'S,8a'S)-1-benzyl-6'-ethyl-4-methoxy-3-oxo-3',5',6',7',8',8a'-hexahydro-2'H-spiro[indoline-2,1'-indolizine]-7'-yl)-3-methoxyacrylate

ID: ALA4476666

PubChem CID: 155538541

Max Phase: Preclinical

Molecular Formula: C30H36N2O5

Molecular Weight: 504.63

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC[C@@H]1CN2CC[C@@]3(C(=O)c4c(OC)cccc4N3Cc3ccccc3)[C@@H]2C[C@@H]1/C(=C\OC)C(=O)OC

Standard InChI:  InChI=1S/C30H36N2O5/c1-5-21-18-31-15-14-30(26(31)16-22(21)23(19-35-2)29(34)37-4)28(33)27-24(12-9-13-25(27)36-3)32(30)17-20-10-7-6-8-11-20/h6-13,19,21-22,26H,5,14-18H2,1-4H3/b23-19+/t21-,22+,26+,30+/m1/s1

Standard InChI Key:  OATYCYBMQGFTJB-PAKGBSETSA-N

Molfile:  

 
     RDKit          2D

 38 42  0  0  0  0  0  0  0  0999 V2000
   27.0797   -3.6889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7645   -4.4539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2690   -5.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0887   -4.9969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4015   -4.2275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8951   -3.5774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0233   -2.4248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3239   -2.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5747   -1.8163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3155   -2.0166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3143   -2.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0291   -3.2569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0273   -1.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7427   -2.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7476   -2.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5394   -3.0962    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.5316   -1.7516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2355   -2.9691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.4353   -3.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1795   -3.9052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7203   -4.5168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5205   -4.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7798   -3.5754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0249   -0.7789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3091   -0.3685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7832   -0.9660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.0681   -4.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8762   -4.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4594   -5.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6512   -5.4649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0068   -5.9166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8151   -5.7513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.3625   -6.3685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3903   -6.2476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1038   -4.8476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3820   -5.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4315   -3.9171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8519   -3.7175    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7 19  1  0
 18  8  1  0
  8  9  1  0
  9  7  1  0
 10 11  2  0
 11 12  1  0
 12 15  2  0
 14 13  2  0
 13 10  1  0
 14 15  1  0
 15 16  1  0
  7 16  1  1
  7 17  1  0
 17 14  1  0
 18 19  1  0
 18 23  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 13 24  1  0
 24 25  1  0
 17 26  2  0
 22 27  1  1
 27 28  1  0
 21 29  1  1
 29 30  1  0
 29 31  2  0
 31 32  1  0
 32 33  1  0
 30 34  2  0
 30 35  1  0
 35 36  1  0
 16 37  1  0
 37  5  1  0
 19 38  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4476666

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 504.63

Molecular Weight (Monoisotopic): 504.2624

AlogP: 4.46

#Rotatable Bonds: 7

Polar Surface Area: 68.31

Molecular Species: BASE

HBA: 7

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.73

CX LogP: 4.59

CX LogD: 2.29

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.31

Np Likeness Score: 0.97

References

1. Váradi A, Marrone GF, Palmer TC, Narayan A, Szabó MR, Le Rouzic V, Grinnell SG, Subrath JJ, Warner E, Kalra S, Hunkele A, Pagirsky J, Eans SO, Medina JM, Xu J, Pan YX, Borics A, Pasternak GW, McLaughlin JP, Majumdar S..  (2016)  Mitragynine/Corynantheidine Pseudoindoxyls As Opioid Analgesics with Mu Agonism and Delta Antagonism, Which Do Not Recruit β-Arrestin-2.,  59  (18): [PMID:27556704] [10.1021/acs.jmedchem.6b00748]

Source

Source(1):

• Scientific Literature