Ralfuranone I

ID: ALA3325771

PubChem CID: 102530848

Max Phase: Preclinical

Molecular Formula: C18H12O4

Molecular Weight: 292.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)C1=C(c2ccccc2)/C(=C/c2ccccc2)C(=O)O1

Standard InChI:  InChI=1S/C18H12O4/c19-17(20)16-15(13-9-5-2-6-10-13)14(18(21)22-16)11-12-7-3-1-4-8-12/h1-11H,(H,19,20)/b14-11-

Standard InChI Key:  HXJRAGITJNXHBB-KAMYIIQDSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   10.9660  -18.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7832  -18.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0376  -17.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3746  -16.8680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7159  -17.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8185  -17.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4250  -17.6444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9895  -16.2976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2613  -18.7863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9264  -19.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4053  -20.1942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2190  -20.1101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5516  -19.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0707  -18.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4848  -18.7873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6722  -18.7008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3450  -17.9513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5332  -17.8645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0511  -18.5255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3866  -19.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1975  -19.3584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9386  -17.0979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  6  7  1  0
  6  8  2  0
  3  6  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  2  9  1  0
  1 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
  5 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3325771

   (4Z)-4-benzylidene-5-oxo-3-phenylfuran-2-carboxylic acid

Molecule Features

Natural Product: No

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: 292.29

Molecular Weight (Monoisotopic): 292.0736

AlogP: 3.12

#Rotatable Bonds: 3

Polar Surface Area: 63.60

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.65

CX Basic pKa: ┄

CX LogP: 3.46

CX LogD: -0.04

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.70

Np Likeness Score: 0.10

References

1. Pauly J, Nett M, Hoffmeister D..  (2014)  Ralfuranone Is Produced by an Alternative Aryl-Substituted γ-Lactone Biosynthetic Route in Ralstonia solanacearum.,  77  (8): [PMID:25033087] [10.1021/np500263r]

Source

Source(1):

• Scientific Literature