(+/-)-Peniphenone E

ID: ALA4475663

PubChem CID: 54680454

Max Phase: Preclinical

Molecular Formula: C16H16O8

Molecular Weight: 336.30

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)c1cc(C)c(O)c(CC2=C(O)C(CC(=O)O)OC2=O)c1O

Standard InChI:  InChI=1S/C16H16O8/c1-6-3-8(7(2)17)14(21)9(13(6)20)4-10-15(22)11(5-12(18)19)24-16(10)23/h3,11,20-22H,4-5H2,1-2H3,(H,18,19)

Standard InChI Key:  UUIXAUNVUMHZTJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   14.5447   -2.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5435   -3.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2583   -4.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9748   -3.7685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9720   -2.9381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2565   -2.5289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6899   -4.1799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6912   -5.0050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0254   -5.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2815   -6.2700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1067   -6.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3603   -5.4836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1437   -5.2251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5927   -6.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2584   -7.6895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7444   -8.3562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4380   -7.7771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6849   -2.5228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2541   -1.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9674   -1.2892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5384   -1.2936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8288   -4.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2581   -5.0070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2004   -5.4856    0.0000 O   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
  4  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  8  2  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
  5 18  1  0
  6 19  1  0
 19 20  2  0
 19 21  1  0
  2 22  1  0
  3 23  1  0
  9 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4475663

   (+/-)-peniphenone E

Molecule Features

Natural Product: Yes

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: 336.30

Molecular Weight (Monoisotopic): 336.0845

AlogP: 1.36

#Rotatable Bonds: 5

Polar Surface Area: 141.36

Molecular Species: ACID

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.32

CX Basic pKa: ┄

CX LogP: 1.73

CX LogD: -4.19

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.47

Np Likeness Score: 1.39

References

1. El-Kashef DH, Daletos G, Plenker M, Hartmann R, Mándi A, Kurtán T, Weber H, Lin W, Ancheeva E, Proksch P..  (2019)  Polyketides and a Dihydroquinolone Alkaloid from a Marine-Derived Strain of the Fungus Metarhizium marquandii.,  82  (9): [PMID:31432669] [10.1021/acs.jnatprod.9b00125]

Source

Source(1):

• Scientific Literature