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

ID: ALA1688935

Cas Number: 52151-92-5

PubChem CID: 10247670

Max Phase: Preclinical

Molecular Formula: C20H20O6

Molecular Weight: 356.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc([C@H]2OC[C@H]3[C@@H]2CO[C@@H]3c2ccc3c(c2)OCO3)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-AFHBHXEDSA-N

Molfile:  

     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
   14.5554   -0.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0667   -1.0293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5514   -1.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3387   -0.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3363   -1.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1202   -1.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6071   -1.0368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1241   -0.3680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3333    0.2083    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.3292   -2.2667    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.3814    0.4159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2945   -2.4797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1942    0.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0900    1.8071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8364    1.0243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4863   -2.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5911   -3.8735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8443   -3.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9011    1.9798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4491    1.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2039    1.6951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3172    2.6911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7801   -4.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2249   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4661   -3.7664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5524   -4.5923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3645   -4.7652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8686    1.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
 11 13  2  0
 21 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1688935

   Piperitol

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