Paleacenin B

ID: ALA4518615

PubChem CID: 155541596

Max Phase: Preclinical

Molecular Formula: C36H48O8

Molecular Weight: 608.77

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCC(=O)c1c(O)c(CC2=C(O)[C@](C)(C/C=C(\C)CCC=C(C)C)C(O)=C(C(C)=O)C2=O)c(O)c(CC=C(C)C)c1OC

Standard InChI:  InChI=1S/C36H48O8/c1-10-12-27(38)29-31(40)25(30(39)24(33(29)44-9)16-15-21(4)5)19-26-32(41)28(23(7)37)35(43)36(8,34(26)42)18-17-22(6)14-11-13-20(2)3/h13,15,17,39-40,42-43H,10-12,14,16,18-19H2,1-9H3/b22-17+/t36-/m0/s1

Standard InChI Key:  FDKOJCRVMVQXER-YYDUIWCQSA-N

Molfile:  

 
     RDKit          2D

 44 45  0  0  0  0  0  0  0  0999 V2000
    9.2023  -13.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2012  -14.5384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8968  -14.9432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5941  -14.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5913  -13.7318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8950  -13.3348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5110  -13.3352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8926  -12.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5867  -12.1316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1960  -12.1359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2791  -12.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9732  -12.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2809  -13.3288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9778  -13.7264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8966  -15.7439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9738  -14.9571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7740  -12.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1785  -13.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5786  -12.6433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4892  -13.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4892  -14.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1821  -14.9406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8750  -14.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8750  -13.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1821  -15.7454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7986  -14.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1027  -14.5464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7998  -15.7505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5669  -13.3446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9733  -12.6483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5708  -11.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7702  -11.9567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9690  -11.2618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3677  -11.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5670  -11.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1645  -10.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3638  -10.5776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5627   -9.8786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7964  -13.3462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2859  -14.9413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2872  -15.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9832  -16.1412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9845  -16.9419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6737  -15.7398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  2  0
  9 11  1  0
 11 12  1  0
  5 13  1  0
 13 14  1  0
  3 15  1  0
  2 16  1  0
 18 17  1  1
 19 18  1  0
 20 21  2  0
 20 18  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 18  1  0
 22 25  2  0
 21 26  1  0
 26 27  2  0
 26 28  1  0
 24 29  1  0
 23 16  1  0
 17 30  1  0
 30 31  2  0
 31 32  1  0
 31 33  1  0
 32 34  1  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 36 38  1  0
 20 39  1  0
  4 40  1  0
 40 41  1  0
 41 42  2  0
 42 43  1  0
 42 44  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4518615

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 608.77

Molecular Weight (Monoisotopic): 608.3349

AlogP: 8.03

#Rotatable Bonds: 14

Polar Surface Area: 141.36

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.17

CX Basic pKa: ┄

CX LogP: 7.81

CX LogD: 2.32

Aromatic Rings: 1

Heavy Atoms: 44

QED Weighted: 0.09

Np Likeness Score: 2.22

References

1. Arvizu-Espinosa MG, von Poser GL, Henriques AT, Mendoza-Ruiz A, Cardador-Martínez A, Gesto-Borroto R, Núñez-Aragón PN, Villarreal-Ortega ML, Sharma A, Cardoso-Taketa A..  (2019)  Bioactive Dimeric Acylphloroglucinols from the Mexican Fern Elaphoglossum paleaceum.,  82  (4): [PMID:30920216] [10.1021/acs.jnatprod.8b00677]

Source

Source(1):

• Scientific Literature