(1R,5R)-6-(4-hydroxy-3-methoxyphenyl)-2-(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo-[3,3,0]octane

ID: ALA1688938

PubChem CID: 53318803

Max Phase: Preclinical

Molecular Formula: C20H20O6

Molecular Weight: 356.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C2OC[C@@H]3C(c4ccc5c(c4)OCO5)OC[C@H]23)ccc1O

Standard InChI:  InChI=1S/C20H20O6/c1-22-17-6-11(2-4-15(17)21)19-13-8-24-20(14(13)9-23-19)12-3-5-16-18(7-12)26-10-25-16/h2-7,13-14,19-21H,8-10H2,1H3/t13-,14-,19?,20?/m0/s1

Standard InChI Key:  VBIRCRCPHNUJAS-NILVNCKXSA-N

Molfile:  

     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
    1.6018   -3.2345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3839   -2.9699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8782   -3.6298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3986   -4.3046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6111   -4.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8326   -4.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3406   -3.6594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8145   -2.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6290   -2.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0705   -1.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3156   -0.7879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1205   -0.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6768   -1.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4317   -2.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4396    0.5401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8939   -0.0817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1955    0.2143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5863   -5.1068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1461   -5.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8974   -6.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0948   -6.6802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4637   -6.0776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2186   -5.2879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4594   -7.1075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2131   -7.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1503   -7.4699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5913   -2.4071    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6240   -4.8799    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  1  8  1  0
  1  5  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  9 14  2  0
 15 16  1  0
 15 17  1  0
 11 16  1  0
 12 17  1  0
  2  9  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 18 23  2  0
 24 25  1  0
 20 24  1  0
 21 26  1  0
  6 18  1  0
  1 27  1  1
  5 28  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1688938

   4-[(3aR,6aR)-3-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2-methoxyphenol

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: 356.37

Molecular Weight (Monoisotopic): 356.1260

AlogP: 3.20

#Rotatable Bonds: 3

Polar Surface Area: 66.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.91

CX Basic pKa: ┄

CX LogP: 2.36

CX LogD: 2.36

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.91

Np Likeness Score: 1.07

References

1. Hamada N, Tanaka A, Fujita Y, Itoh T, Ono Y, Kitagawa Y, Tomimori N, Kiso Y, Akao Y, Nozawa Y, Ito M..  (2011)  Involvement of heme oxygenase-1 induction via Nrf2/ARE activation in protection against H2O2-induced PC12 cell death by a metabolite of sesamin contained in sesame seeds.,  19  (6): [PMID:21345685] [10.1016/j.bmc.2011.01.059]

Source

Source(1):

• Scientific Literature