5-(6-hydroxybenzofuran-2-yl)-2,2-dimethyl-2Hchromen-7-ol

ID: ALA3397311

Cas Number: 73338-84-8

PubChem CID: 5319888

Max Phase: Preclinical

Molecular Formula: C19H16O4

Molecular Weight: 308.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)C=Cc2c(cc(O)cc2-c2cc3ccc(O)cc3o2)O1

Standard InChI:  InChI=1S/C19H16O4/c1-19(2)6-5-14-15(8-13(21)10-18(14)23-19)17-7-11-3-4-12(20)9-16(11)22-17/h3-10,20-21H,1-2H3

Standard InChI Key:  GDSYWTBPYYYLLE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   -2.0527    7.8772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5577    7.8863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2160    6.5784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8104    6.5599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0368    5.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5418    5.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0773    3.8600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2919    2.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4839    3.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0336    8.9306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6486   -1.3517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6176   -0.1242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5647   -1.9483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  2 10  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 17  1  0
 16 11  1  0
  8 11  1  0
 13 15  1  0
 16 17  2  0
 16 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 19 22  1  0
 19 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3397311

   Moracin E

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: 308.33

Molecular Weight (Monoisotopic): 308.1049

AlogP: 4.70

#Rotatable Bonds: 1

Polar Surface Area: 62.83

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.87

CX Basic pKa: ┄

CX LogP: 3.99

CX LogD: 3.98

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.68

Np Likeness Score: 2.15

References

1. Naik R, Harmalkar DS, Xu X, Jang K, Lee K..  (2015)  Bioactive benzofuran derivatives: moracins A-Z in medicinal chemistry.,  90  [PMID:25461329] [10.1016/j.ejmech.2014.11.047]

2. Kishore N, Kumar P, Shanker K, Verma AK..  (2019)  Human disorders associated with inflammation and the evolving role of natural products to overcome.,  179  [PMID:31255927] [10.1016/j.ejmech.2019.06.034]

Source

Source(1):

• Scientific Literature