Anhyfrodebromoa-aplysiatoxin

ID: ALA5266525

Max Phase: Preclinical

Molecular Formula: C32H46O9

Molecular Weight: 574.71

Names and Identifiers

Canonical SMILES:  CO[C@@H](CC[C@H](C)[C@H]1O[C@]23C[C@H](OC(=O)C[C@@H]([C@@H](C)O)OC(=O)CC(=C(C)CC2(C)C)O3)[C@@H]1C)c1cccc(O)c1

Standard InChI:  InChI=1S/C32H46O9/c1-18(11-12-24(37-7)22-9-8-10-23(34)13-22)30-20(3)27-17-32(41-30)31(5,6)16-19(2)25(40-32)14-28(35)38-26(21(4)33)15-29(36)39-27/h8-10,13,18,20-21,24,26-27,30,33-34H,11-12,14-17H2,1-7H3/t18-,20-,21+,24-,26-,27-,30+,32+/m0/s1

Standard InChI Key:  HCEQACRMJXGKHI-MDFDFFFMSA-N

Molfile:  

 
     RDKit          2D

 43 46  0  0  0  0  0  0  0  0999 V2000
   -4.2859   -0.9765    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5714   -1.3891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5714   -0.5640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2859   -0.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2859    0.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5716    1.0867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5716    1.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2859    2.3245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8568    2.3247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1421    1.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1421    1.0867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4134    0.8267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0015   -0.1511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7158   -0.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7158   -1.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4304   -0.1511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1449   -0.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8593   -0.1511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8593    0.6738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1449    1.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5738   -0.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5738   -1.3921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2902   -1.8002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2902   -2.6253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0003   -1.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0003   -0.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2884   -0.1513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7130   -0.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7130   -1.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4274   -0.1511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4274   -0.9760    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4274    0.6741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1422   -0.5637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1422   -1.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4277   -1.8015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8569   -1.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8568    0.6741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7296    2.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3156    1.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0003   -0.5640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2859   -1.8015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0003   -1.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2859   -2.6265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  7  6  2  0
  7  8  1  0
  7  9  1  0
 10  9  1  0
 11 10  1  0
 11 12  1  0
 13 12  1  6
 13 14  1  0
 14 15  1  6
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  6
 19 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 21  2  0
 28 13  1  0
 28 29  1  1
 30 28  1  0
 30 31  1  6
 30 32  1  0
 11 32  1  6
 30 33  1  0
 34 33  1  0
 34 35  2  0
 36 34  1  0
 36  2  1  0
 37 11  1  0
  6 37  1  0
 10 38  1  0
 10 39  1  0
  4 40  2  0
  2 41  1  0
 41 42  1  0
 41 43  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA5266525

   ---

Molecule Features

Natural Product: Yes

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: 574.71

Molecular Weight (Monoisotopic): 574.3142

AlogP: 5.34

#Rotatable Bonds: 7

Polar Surface Area: 120.75

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.36

CX Basic pKa: ┄

CX LogP: 5.12

CX LogD: 5.11

Aromatic Rings: 1

Heavy Atoms: 41

QED Weighted: 0.42

Np Likeness Score: 1.53

References

1. Xu J, Zhang T, Yao J, Lu J, Liu Z, Ding L..  (2020)  Recent advances in chemistry and bioactivity of marine cyanobacteria Moorea species.,  201  [PMID:32652435] [10.1016/j.ejmech.2020.112473]

Source

Source(1):

• Scientific Literature