3',4',4a',9a'-tetrahydro-6,7'-dimethylspiro[benzofuran-3(2H),2'-pyrano[2,3-b]benzofuran]-2,4a'-diol

ID: ALA486806

PubChem CID: 44559245

Max Phase: Preclinical

Molecular Formula: C20H20O5

Molecular Weight: 340.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc2c(c1)O[C@H]1O[C@@]3(CC[C@@]21O)c1ccc(C)cc1O[C@@H]3O

Standard InChI:  InChI=1S/C20H20O5/c1-11-3-5-13-15(9-11)24-18-19(13,22)7-8-20(25-18)14-6-4-12(2)10-16(14)23-17(20)21/h3-6,9-10,17-18,21-22H,7-8H2,1-2H3/t17-,18-,19+,20-/m0/s1

Standard InChI Key:  YMKQULZUUJUBPP-HAGHYFMRSA-N

Molfile:  

     RDKit          2D

 26 30  0  0  0  0  0  0  0  0999 V2000
    6.2023   -0.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9481    0.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8063    0.6457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0931    0.2316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1005   -0.5970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8171   -1.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5224    0.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5216   -0.5837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3050   -0.8420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3061    0.4923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7921   -0.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6099   -0.0953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4622    1.3288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6379    1.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0279   -0.1256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6182    1.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2860    0.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0386    0.9911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1246    1.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4520    2.2981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7020    1.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3873   -1.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8850    1.2112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1967   -0.8913    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1977   -0.9552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8803    2.1520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  5  6  2  0
 10 14  1  0
 11 12  1  0
 12  2  1  0
  2 13  1  6
 13 14  1  0
  6  8  1  0
 17 15  1  0
  7  8  2  0
 16 17  2  0
  7  3  1  0
 17 18  1  0
  1 15  1  0
 18 19  2  0
  8  9  1  0
 19 20  1  0
  9 11  1  0
 20 21  2  0
 21 16  1  0
 10  7  1  0
  5 22  1  0
 10 11  1  0
 10 23  1  1
  3  4  2  0
 11 24  1  1
  2 16  1  0
  1 25  1  6
  4  5  1  0
 19 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA486806

   3',4',4a',9a'-tetrahydro-6,7'-dimethylspiro[benzofuran-3(2H),2'-pyrano[2,3-b]benzofuran]-2,4a'-diol

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: 340.38

Molecular Weight (Monoisotopic): 340.1311

AlogP: 2.63

#Rotatable Bonds: ┄

Polar Surface Area: 68.15

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.89

CX Basic pKa: ┄

CX LogP: 3.59

CX LogD: 3.59

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.77

Np Likeness Score: 1.79

References

1. Pérez-Vásquez A, Reyes A, Linares E, Bye R, Mata R..  (2005)  Phytotoxins from Hofmeisteria schaffneri: isolation and synthesis of 2'-(2' '-hydroxy-4' '-methylphenyl)-2'-oxoethyl acetate1.,  68  (6): [PMID:15974630] [10.1021/np0501278]

Source

Source(1):

• Scientific Literature