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

ID: ALA1688936

Cas Number: 1105568-81-7

PubChem CID: 53325346

Product Number: E356065, Order Now?

Max Phase: Preclinical

Molecular Formula: C19H18O6

Molecular Weight: 342.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1ccc(C2OC[C@@H]3C(c4ccc5c(c4)OCO5)OC[C@H]23)cc1O

Standard InChI:  InChI=1S/C19H18O6/c20-14-3-1-10(5-15(14)21)18-12-7-23-19(13(12)8-22-18)11-2-4-16-17(6-11)25-9-24-16/h1-6,12-13,18-21H,7-9H2/t12-,13-,18?,19?/m0/s1

Standard InChI Key:  CGEORJKFOZSMEZ-IJKBLAIYSA-N

Molfile:  

     RDKit          2D

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   -1.0308   -2.4272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5188   -1.7675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0423   -1.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2536   -1.3442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5260   -1.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0153   -1.7459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5388   -2.4175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2791   -3.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7230   -3.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9712   -4.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7768   -4.7874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3342   -4.1767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0846   -3.3938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1005   -5.9370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5524   -5.3174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4678    1.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2734    1.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8295    0.6690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5812   -0.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5216    2.0626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0895    1.7068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2439   -2.9909    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2631   -0.5203    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  0
  3  4  1  0
  5  4  1  0
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  2  9  1  0
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 20 25  1  0
  6 18  1  0
  1 26  1  1
  5 27  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1688936

   epi-Sesamin Monocatechol

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: 342.35

Molecular Weight (Monoisotopic): 342.1103

AlogP: 2.90

#Rotatable Bonds: 2

Polar Surface Area: 77.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.21

CX Basic pKa: ┄

CX LogP: 2.22

CX LogD: 2.21

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.82

Np Likeness Score: 1.16

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