Aspulvinone O

ID: ALA5182428

Cas Number: 914071-54-8

PubChem CID: 54703017

Max Phase: Preclinical

Molecular Formula: C27H28O6

Molecular Weight: 448.52

Names and Identifiers

Canonical SMILES:  CC(C)=CCc1cc(/C=C2\OC(=O)C(c3cc(CC=C(C)C)c(O)cc3O)=C2O)ccc1O

Standard InChI:  InChI=1S/C27H28O6/c1-15(2)5-8-18-11-17(7-10-21(18)28)12-24-26(31)25(27(32)33-24)20-13-19(9-6-16(3)4)22(29)14-23(20)30/h5-7,10-14,28-31H,8-9H2,1-4H3/b24-12-

Standard InChI Key:  IAHWCROWFXOMDG-MSXFZWOLSA-N

Molfile:  

 
     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   -1.6794   -1.9225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648   -1.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2529   -1.9221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2529   -2.7473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9630   -3.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6794   -2.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9630   -3.9843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3940   -3.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1087   -2.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8233   -3.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5379   -2.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8233   -3.9887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648   -0.6850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2502   -0.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2502    0.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5539    0.8028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0247    0.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5326   -0.5183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8499    0.1491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648    0.9652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7675    1.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1841    2.1836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3977    2.9781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1951    3.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7767    2.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5679    1.8144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4087    3.9887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5738    2.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1574    2.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9545    2.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5379    1.8724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1680    3.2529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6129    1.9700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  5  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
  2 13  1  0
 13 14  2  0
 15 14  1  0
 15 16  2  0
 16 17  1  0
 18 17  1  0
 14 18  1  0
 17 19  2  0
 15 20  1  0
 16 21  1  0
 22 21  2  0
 23 22  1  0
 24 23  2  0
 25 24  1  0
 26 25  2  0
 21 26  1  0
 24 27  1  0
 25 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 30 32  1  0
 22 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5182428

   Aspulvinone O

Molecule Features

Natural Product: No

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: 448.52

Molecular Weight (Monoisotopic): 448.1886

AlogP: 5.69

#Rotatable Bonds: 6

Polar Surface Area: 107.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.61

CX Basic pKa: ┄

CX LogP: 5.90

CX LogD: 5.03

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.33

Np Likeness Score: 1.27

References

1. Wu Q, Sun Z, Chen Z, Liu J, Ding H, Luo C, Wang M, Du D..  (2022)  The discovery of a non-competitive GOT1 inhibitor, hydralazine hydrochloride, via a coupling reaction-based high-throughput screening assay.,  73  [PMID:35820623] [10.1016/j.bmcl.2022.128883]

2. Liang XX, Zhang XJ, Zhao YX, Feng J, Zeng JC, Shi QQ, Kaunda JS, Li XL, Wang WG, Xiao WL..  (2022)  Aspulvins A-H, Aspulvinone Analogues with SARS-CoV-2 M^pro Inhibitory and Anti-inflammatory Activities from an Endophytic Cladosporium sp.,  85  (4.0): [PMID:35293744] [10.1021/acs.jnatprod.1c01003]

Source

Source(1):

• Scientific Literature