Banksialactone H

ID: ALA4168443

PubChem CID: 145953218

Max Phase: Preclinical

Molecular Formula: C23H26O9

Molecular Weight: 446.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(O)c2c(c1C)[C@H](C)[C@](O)(COC(=O)c1c(C)c(C)c(O)c(C)c1O)OC2=O

Standard InChI:  InChI=1S/C23H26O9/c1-9-10(2)19(25)12(4)20(26)17(9)21(27)31-8-23(29)13(5)16-11(3)15(30-6)7-14(24)18(16)22(28)32-23/h7,13,24-26,29H,8H2,1-6H3/t13-,23-/m0/s1

Standard InChI Key:  LAONCLCOCCMFGL-NPMABZOXSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   14.8151  -10.6456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8140  -11.4731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5287  -11.8859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5269  -10.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5285  -12.7109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5245   -9.4079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0991  -11.8850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3849  -11.4719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2423  -10.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2412  -11.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9541  -11.8835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6728  -11.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6739  -10.6440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9564  -10.2265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9564   -9.4016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3860  -11.8870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1017  -11.4765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9518  -12.7085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6664  -12.2958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8149  -11.8910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5306  -11.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8126  -12.7160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2413  -11.8986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9565  -11.4888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9592  -10.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2408  -10.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5287  -10.6608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8135  -10.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2402   -9.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2367  -12.7236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6743  -10.2515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6695  -11.9036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3 10  2  0
  9  4  2  0
  4  1  1  0
  3  5  1  0
  4  6  1  0
  2  7  1  0
  7  8  1  0
  9 10  1  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 12 16  1  1
 16 17  1  0
 11 18  1  1
 12 19  1  0
 17 20  1  0
 20 21  1  0
 20 22  2  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 21  1  0
 27 28  1  0
 26 29  1  0
 23 30  1  0
 25 31  1  0
 24 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4168443

   ---

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: 446.45

Molecular Weight (Monoisotopic): 446.1577

AlogP: 2.87

#Rotatable Bonds: 4

Polar Surface Area: 142.75

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.28

CX Basic pKa: ┄

CX LogP: 6.03

CX LogD: 6.02

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.52

Np Likeness Score: 1.40

References

1. Chaudhary NK, Pitt JI, Lacey E, Crombie A, Vuong D, Piggott AM, Karuso P..  (2018)  Banksialactones and Banksiamarins: Isochromanones and Isocoumarins from an Australian Fungus, Aspergillus banksianus.,  81  (7): [PMID:29920099] [10.1021/acs.jnatprod.7b00816]

Source

Source(1):

• Scientific Literature