methyl 4-isopropenyl-12-methyl-18-oxo-(4S,12R,14R)-11,19,20-trioxapentacyclo[12.3.2.16,9.01,15.010,12]icosa-6,8,16-triene-7-carboxylate (pukalide)

ID: ALA300390

PubChem CID: 21574603

Max Phase: Preclinical

Molecular Formula: C21H24O6

Molecular Weight: 372.42

Molecule Type: Small molecule

Names and Identifiers

Synonyms: pukalide | Pukalide|CHEMBL300390|SCHEMBL1760554|methyl (2R,4S,6R,12S)-4-methyl-8-oxo-12-prop-1-en-2-yl-3,7,17-trioxatetracyclo[12.2.1.16,9.02,4]octadeca-1(16),9(18),14-triene-15-carboxylate

Canonical SMILES:  C=C(C)[C@H]1CCC2=C[C@@H](C[C@]3(C)O[C@H]3c3cc(C(=O)OC)c(o3)C1)OC2=O

Standard InChI:  InChI=1S/C21H24O6/c1-11(2)12-5-6-13-7-14(25-19(13)22)10-21(3)18(27-21)17-9-15(20(23)24-4)16(8-12)26-17/h7,9,12,14,18H,1,5-6,8,10H2,2-4H3/t12-,14-,18-,21-/m0/s1

Standard InChI Key:  PPHCYWKQJLNLQQ-TVVYHTAVSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  1  0  0  0  0  0999 V2000
    4.9875   -6.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6167   -6.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3750   -6.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9500   -5.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1750   -6.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1375   -6.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3875   -5.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6625   -6.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9375   -8.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0750   -7.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625   -8.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2875   -4.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6292   -7.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1750   -7.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6625   -7.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7042   -6.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9792   -6.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5875   -6.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2625   -8.7417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667   -7.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8875   -5.0417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667   -7.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8792   -6.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5125   -6.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0417   -4.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9000   -7.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3875   -3.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4531   -8.4837    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3685   -6.9636    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  1  3  1  0
  4  7  1  0
  5  2  1  0
  6  8  1  0
  7  5  2  0
  8  5  1  0
  9 11  1  0
 10 15  2  0
 14 11  1  0
 12  4  1  0
 13  1  1  0
 14 13  1  0
 15 14  1  0
 16  6  1  0
 17 16  1  0
 17 18  1  1
 19  9  2  0
 20 10  1  0
 21 12  2  0
 22 20  1  0
 23 18  2  0
  1 24  1  1
 25 12  1  0
 26 18  1  0
 27 25  1  0
  2  3  1  0
 10  9  1  0
  6  4  2  0
 17 22  1  0
 14 28  1  1
  2 29  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA300390

   PUKALIDE

Molecule Features

Natural Product: Yes

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: 372.42

Molecular Weight (Monoisotopic): 372.1573

AlogP: 3.67

#Rotatable Bonds: 2

Polar Surface Area: 78.27

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.02

CX Basic pKa: ┄

CX LogP: 3.40

CX LogD: 3.40

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.45

Np Likeness Score: 2.77

References

1. Abramson SN, Trischman JA, Tapiolas DM, Harold EE, Fenical W, Taylor P..  (1991)  Structure/activity and molecular modeling studies of the lophotoxin family of irreversible nicotinic receptor antagonists.,  34  (6): [PMID:1676426] [10.1021/jm00110a007]

Source

Source(1):

• Scientific Literature