methyl 2-[7,12-dimethyl-2,5-di (methylcarbonyloxy)-17-oxo-(2S,4R,5R,12R,14R)-11,16,18,19-tetraoxapentacyclo[12.2.2.16,9.01,15.010,12]nonadeca-6,8-dien-4-yl]acrylate (Bipinnatin-A)

ID: ALA299534

PubChem CID: 10413791

Max Phase: Preclinical

Molecular Formula: C25H28O11

Molecular Weight: 504.49

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Bipinnatin-A | CHEMBL299534

Canonical SMILES:  C=C(C(=O)OC)[C@H]1C[C@H](OC(C)=O)[C@@]23O[C@@H]2[C@@H](C[C@]2(C)O[C@H]2c2cc(C)c(o2)[C@@H]1OC(C)=O)OC3=O

Standard InChI:  InChI=1S/C25H28O11/c1-10-7-15-20-24(5,35-20)9-16-21-25(36-21,23(29)34-16)17(31-12(3)26)8-14(11(2)22(28)30-6)19(18(10)33-15)32-13(4)27/h7,14,16-17,19-21H,2,8-9H2,1,3-6H3/t14-,16-,17+,19-,20+,21-,24+,25-/m1/s1

Standard InChI Key:  SETTUTVEWZFWRZ-FEXMGBQDSA-N

Molfile:  

     RDKit          2D

 39 43  0  0  1  0  0  0  0  0999 V2000
    5.8250   -7.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3500   -6.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6750   -6.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9125   -6.6167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3042   -5.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0625   -6.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6250   -7.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8625   -5.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8250   -5.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3500   -5.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3917   -5.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667   -6.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8625   -7.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3542   -7.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0500   -7.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6375   -4.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2750   -6.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0750   -4.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3167   -6.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3542   -6.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5875   -6.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7667   -5.1000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3542   -7.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9250   -4.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9500   -8.1125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5125   -8.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5750   -5.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1875   -6.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917   -4.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0875   -8.5125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2000   -6.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3000   -7.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9750   -4.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -8.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5000   -4.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6000   -7.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1406   -7.8545    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0545   -6.3361    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8119   -7.7119    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3 19  1  0
  1  4  1  1
  5  3  1  0
  3  6  1  0
  7  1  1  0
  8  5  1  0
  9 11  1  0
 10  9  1  0
 11 12  1  0
 12 20  1  0
 13  2  1  0
 14  1  1  0
 15  7  1  0
 16  9  2  0
 12 17  1  1
 18 16  1  0
 19 13  1  0
 20 14  1  0
 21 17  1  0
 11 22  1  6
 14 23  1  6
 24 22  1  0
 25  7  2  0
 26 23  1  0
 27 17  2  0
 28 21  2  0
 29 24  2  0
 30 26  2  0
  3 31  1  1
 32 21  1  0
 33 16  1  0
 34 26  1  0
 35 24  1  0
 36 32  1  0
  2  4  1  0
 13 15  1  0
  5  6  1  0
  8 10  1  0
  8 18  2  0
 13 37  1  1
  5 38  1  6
  2 39  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA299534

   methyl 2-[(1R,2S,4R,5R,10R,12S,14R,15R)-2,5-diacetyloxy-7,12-dimethyl-17-oxo-11,16,18,19-tetraoxapentacyclo[12.2.2.16,9.01,15.010,12]nonadeca-6,8-dien-4-yl]prop-2-enoate

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: 504.49

Molecular Weight (Monoisotopic): 504.1632

AlogP: 2.16

#Rotatable Bonds: 4

Polar Surface Area: 143.40

Molecular Species: NEUTRAL

HBA: 11

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.54

CX LogD: 1.54

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.26

Np Likeness Score: 2.86

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