4-(1-formylvinyl)-7,12-dimethyl-2-methylcarbonyloxy-17-oxo-(2S,4R,5R,12R)-11,16,18,19-tetraoxapentacyclo[12.2.2.16,9.01,15.010,12]nonadeca-6,8-dien-5-yl acetate (Bipinnatin-B)

ID: ALA51553

PubChem CID: 10390134

Max Phase: Preclinical

Molecular Formula: C24H26O10

Molecular Weight: 474.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C=O)[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/C24H26O10/c1-10-6-15-20-23(5,33-20)8-16-21-24(34-21,22(28)32-16)17(29-12(3)26)7-14(11(2)9-25)19(18(10)31-15)30-13(4)27/h6,9,14,16-17,19-21H,2,7-8H2,1,3-5H3/t14-,16-,17+,19-,20+,21-,23+,24-/m1/s1

Standard InChI Key:  MEFFELURXRIWBN-CHICZLJJSA-N

Molfile:  

     RDKit          2D

 37 41  0  0  1  0  0  0  0  0999 V2000
    5.8250   -7.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3500   -6.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6750   -6.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9125   -6.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3042   -5.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0625   -6.3542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6250   -7.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8625   -5.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8250   -5.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3500   -5.8125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8625   -7.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3917   -5.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3542   -7.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0500   -7.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6375   -4.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0750   -4.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667   -6.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3167   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3542   -6.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7667   -5.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2750   -6.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3542   -7.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9250   -4.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9500   -8.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9292   -8.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4542   -7.8125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917   -4.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5750   -5.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5875   -6.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1875   -6.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2000   -6.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9750   -4.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9292   -8.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5000   -4.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1406   -7.9045    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0545   -6.3861    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8119   -7.7619    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3 18  1  0
  1  4  1  1
  5  3  1  0
  3  6  1  0
  7  1  1  0
  8  5  1  0
  9 12  1  0
 10  9  1  0
 11  2  1  0
 12 17  1  0
 13  1  1  0
 14  7  1  0
 15  9  2  0
 16 15  1  0
 17 19  1  0
 18 11  1  0
 19 13  1  0
 12 20  1  6
 17 21  1  1
 13 22  1  6
 23 20  1  0
 24  7  2  0
 25 22  1  0
 26 25  2  0
 27 23  2  0
 28 21  2  0
 29 21  1  0
 30 29  2  0
  3 31  1  1
 32 15  1  0
 33 25  1  0
 34 23  1  0
  2  4  1  0
 11 14  1  0
  5  6  1  0
 10  8  1  0
 16  8  2  0
 11 35  1  1
  5 36  1  6
  2 37  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA51553

   [(1R,2S,4R,5R,10R,12S,14R,15R)-5-acetyloxy-7,12-dimethyl-17-oxo-4-(3-oxoprop-1-en-2-yl)-11,16,18,19-tetraoxapentacyclo[12.2.2.16,9.01,15.010,12]nonadeca-6,8-dien-2-yl] acetate

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: 474.46

Molecular Weight (Monoisotopic): 474.1526

AlogP: 2.18

#Rotatable Bonds: 4

Polar Surface Area: 134.17

Molecular Species: NEUTRAL

HBA: 10

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.00

CX LogD: 1.00

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.21

Np Likeness Score: 3.05

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