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

ID: ALA1688934

Cas Number: 170713-44-7

PubChem CID: 46917407

Max Phase: Preclinical

Molecular Formula: C19H18O6

Molecular Weight: 342.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1ccc([C@H]2OC[C@H]3[C@@H]2CO[C@@H]3c2ccc3c(c2)OCO3)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-MBZVMHRFSA-N

Molfile:  

     RDKit          2D

 27 31  0  0  0  0  0  0  0  0999 V2000
    6.3804   -0.4531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8917   -1.1210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3764   -1.7874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1637   -0.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1613   -1.5372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9452   -1.7945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4321   -1.1285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9491   -0.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1583    0.1167    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1542   -2.3583    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2064    0.3242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1195   -2.5714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0192    0.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9150    1.7155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6614    0.9326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3113   -2.7396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4161   -3.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6693   -3.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7261    1.8881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2741    1.2725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0289    1.6035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1422    2.5994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6051   -4.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0499   -3.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2911   -3.8581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3774   -4.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1895   -4.8569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11 13  2  0
 13 20  1  0
  3  5  1  0
 19 14  1  0
  5  6  1  0
 14 15  2  0
 15 11  1  0
  6  7  1  0
 12 16  2  0
 16 24  1  0
  7  8  1  0
 23 17  1  0
  8  4  1  0
 17 18  2  0
 18 12  1  0
 19 20  2  0
  4  5  1  0
  4  9  1  1
  5 10  1  1
 20 21  1  0
 22 19  1  0
 23 24  2  0
  4  1  1  0
  8 11  1  1
  1  2  1  0
  3 12  1  1
  2  3  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1688934

   (+)-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]

2. Yasuda K, Ikushiro S, Wakayama S, Itoh T, Yamamoto K, Kamakura M, Munetsuna E, Ohta M, Sakaki T..  (2012)  Comparison of metabolism of sesamin and episesamin by drug-metabolizing enzymes in human liver.,  40  (10): [PMID:22752007] [10.1124/dmd.112.045906]

Source

Source(1):

• Scientific Literature