3-[9-(Ethyl-methyl-amino)-5,9a-dihydroxy-9b-methyl-1,2,3,3a,8,9,9a,9b-octahydro-phenanthro[4,5-bcd]furan-3-ylcarbamoyl]-acrylic acid

ID: ALA2112083

PubChem CID: 13893999

Max Phase: Preclinical

Molecular Formula: C21H24N2O6

Molecular Weight: 400.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CC[C@]23c4c5ccc(O)c4O[C@H]2C(NC(=O)/C=C/C(=O)O)CC[C@@]3(O)[C@H]1C5

Standard InChI:  InChI=1S/C21H24N2O6/c1-23-9-8-20-17-11-2-3-13(24)18(17)29-19(20)12(22-15(25)4-5-16(26)27)6-7-21(20,28)14(23)10-11/h2-5,12,14,19,24,28H,6-10H2,1H3,(H,22,25)(H,26,27)/b5-4+/t12?,14-,19+,20+,21-/m1/s1

Standard InChI Key:  CETFNDSJPGPDOR-JMTSWCSOSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  1  0  0  0  0  0999 V2000
    8.6843   -3.1127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6614   -2.2716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9748   -3.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4127   -3.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9943   -4.3870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0049   -4.2523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9178   -1.8784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2277   -3.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2010   -2.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1312   -3.0815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3742   -1.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8800   -3.4917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6024   -3.0494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2815   -4.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3437   -3.4555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1041   -4.7101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3627   -4.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2311   -1.0110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5222   -3.5901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1101   -2.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0236   -1.2790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5818   -2.1954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8283   -4.2735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5378   -4.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1248   -5.5641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3094   -5.6783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5143   -1.4516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7634   -0.3427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8578   -2.9162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1332   -4.2099    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1422   -1.2472    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
  4  6  1  0
  7  2  1  0
  8  3  1  0
  9  8  1  0
 10  4  1  0
 11  2  1  0
 12 10  1  0
 13 12  1  0
 14  5  1  0
 15 13  1  0
 16 17  1  0
 17 15  2  0
 18  7  1  0
 19  8  2  0
 20 10  1  0
  2 21  1  1
 22 13  2  0
 23 16  2  0
 24 19  1  0
  1 29  1  1
 25 16  1  0
 26 14  1  0
 27 18  1  0
 28 18  1  0
 29 27  1  0
  6  5  1  0
 11 20  1  0
  7  9  1  0
 14 24  2  0
  4 30  1  1
  7 31  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA2112083

   (E)-4-[[(4R,4aS,7aR,12bS)-4a,9-dihydroxy-3-methyl-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]amino]-4-oxobut-2-enoic acid

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: 400.43

Molecular Weight (Monoisotopic): 400.1634

AlogP: 0.30

#Rotatable Bonds: 3

Polar Surface Area: 119.33

Molecular Species: ZWITTERION

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.71

CX Basic pKa: 8.95

CX LogP: -2.36

CX LogD: -2.37

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.54

Np Likeness Score: 1.64

References

1. Botros S, Lipkowski AW, Larson DL, Stark PA, Takemori AE, Portoghese PS..  (1989)  Opioid agonist and antagonist activities of peripherally selective derivatives of naltrexamine and oxymorphamine.,  32  (9): [PMID:2475628] [10.1021/jm00129a009]

Source

Source(1):

• Scientific Literature