17-hydroxy-4-(1-hydroxymethylvinyl)-7,12-dimethyl-2-methylcarbonyloxy-(2S,4R,5R,12R,14R)-11,16,18,19-tetraoxapentacyclo[12.2.2.16,9.01,15.010,12]nonadeca-6,8-dien-5-yl acetate

ID: ALA299395

PubChem CID: 44296257

Max Phase: Preclinical

Molecular Formula: C24H30O10

Molecular Weight: 478.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(CO)[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)OC3O

Standard InChI:  InChI=1S/C24H30O10/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/h6,14,16-17,19-22,25,28H,2,7-9H2,1,3-5H3/t14-,16-,17+,19-,20+,21-,22?,23+,24-/m1/s1

Standard InChI Key:  SNJPTPOTSXBKIB-IFHCYGNOSA-N

Molfile:  

     RDKit          2D

 37 41  0  0  1  0  0  0  0  0999 V2000
    6.1167   -7.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6500   -6.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9667   -6.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2042   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6042   -5.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3542   -6.2875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1625   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167   -5.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9250   -7.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6500   -5.7417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1625   -7.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6917   -5.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6542   -7.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9375   -4.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3500   -7.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3750   -4.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9667   -6.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6167   -6.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6542   -6.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1125   -5.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9667   -7.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5667   -6.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2125   -4.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9625   -8.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3500   -8.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7792   -3.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2417   -8.1000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8667   -5.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5000   -6.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2750   -4.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8875   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6000   -7.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7750   -4.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5667   -8.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4460   -7.8393    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3476   -6.3230    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1118   -7.6995    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  5  1  0
  8 12  1  0
  9  1  1  0
 10  8  1  0
 11  2  1  0
 12 17  1  0
 13  1  1  0
 14  8  2  0
 15  9  1  0
 16 14  1  0
 17 19  1  0
 18 11  1  0
 19 13  1  0
 12 20  1  6
 13 21  1  6
 17 22  1  1
 23 20  1  0
 24 21  1  0
 25 24  2  0
 26 23  2  0
 27  9  1  0
 28 22  2  0
  3 29  1  1
 30 14  1  0
 31 22  1  0
 32 31  1  0
 33 23  1  0
 34 24  1  0
  2  4  1  0
 11 15  1  0
  5  6  1  0
  7 10  1  0
  7 16  2  0
 11 35  1  1
  5 36  1  6
  2 37  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA299395

   [(1R,2S,4R,5R,10R,12S,14R,15R)-5-acetyloxy-17-hydroxy-4-(3-hydroxyprop-1-en-2-yl)-7,12-dimethyl-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: 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: 478.49

Molecular Weight (Monoisotopic): 478.1839

AlogP: 1.77

#Rotatable Bonds: 4

Polar Surface Area: 140.49

Molecular Species: NEUTRAL

HBA: 10

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.08

CX Basic pKa: ┄

CX LogP: 0.35

CX LogD: 0.35

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.37

Np Likeness Score: 2.72

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