Bicuculline

ID: ALA5186559

PubChem CID: 168283089

Max Phase: Preclinical

Molecular Formula: C20H21NO5

Molecular Weight: 355.39

Names and Identifiers

Canonical SMILES:  CN1CCc2cc3c(cc2[C@H]1[C@@H]1OCC2=C1C=CC1OCOC21)OCO3

Standard InChI:  InChI=1S/C20H21NO5/c1-21-5-4-11-6-16-17(25-9-24-16)7-13(11)18(21)20-12-2-3-15-19(26-10-23-15)14(12)8-22-20/h2-3,6-7,15,18-20H,4-5,8-10H2,1H3/t15?,18-,19?,20+/m0/s1

Standard InChI Key:  IKVQQXGYHLZXPD-FOCMDNRUSA-N

Molfile:  

 
     RDKit          2D

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    2.3855  -27.9909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7226  -28.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0526  -28.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7923  -29.2513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3383  -29.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8504  -28.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3939  -28.9138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1399  -29.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6870  -30.3003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4910  -30.1341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7451  -29.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1951  -28.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4278  -31.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4283  -32.4131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9147  -31.7493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6477  -32.1580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6523  -31.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9534  -30.9269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414  -31.3318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9442  -32.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2388  -32.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6297  -32.6960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9571  -33.4427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7685  -33.3606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0359  -30.7473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2127  -31.2885    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8672  -30.2939    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0
  4  2  1  0
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  5  6  2  0
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 20 22  1  0
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 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 21  1  0
 11 26  1  0
 14 27  1  1
 10 28  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA5186559

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 355.39

Molecular Weight (Monoisotopic): 355.1420

AlogP: 1.95

#Rotatable Bonds: 1

Polar Surface Area: 49.39

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.60

CX LogP: 1.63

CX LogD: 1.22

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.77

Np Likeness Score: 1.56

References

1. Bavo F, de-Jong H, Petersen J, Falk-Petersen CB, Löffler R, Sparrow E, Rostrup F, Eliasen JN, Wilhelmsen KS, Barslund K, Bundgaard C, Nielsen B, Kristiansen U, Wellendorph P, Bogdanov Y, Frølund B..  (2021)  Structure-Activity Studies of 3,9-Diazaspiro[5.5]undecane-Based γ-Aminobutyric Acid Type A Receptor Antagonists with Immunomodulatory Effect.,  64  (24.0): [PMID:34908407] [10.1021/acs.jmedchem.1c00290]

Source

Source(1):

• Scientific Literature