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

ID: ALA1688937

PubChem CID: 53321379

Max Phase: Preclinical

Molecular Formula: C18H18O6

Molecular Weight: 330.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1ccc([C@H]2OC[C@H]3[C@@H]2CO[C@H]3c2ccc(O)c(O)c2)cc1O

Standard InChI:  InChI=1S/C18H18O6/c19-13-3-1-9(5-15(13)21)17-11-7-24-18(12(11)8-23-17)10-2-4-14(20)16(22)6-10/h1-6,11-12,17-22H,7-8H2/t11-,12-,17-,18+/m0/s1

Standard InChI Key:  OQSOTSIYXPYTRE-GNTOHDJUSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    1.5895   -1.8308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3774   -1.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8562   -2.2557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3611   -2.9191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5831   -2.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7952   -2.9008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3165   -2.2297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8116   -1.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5342   -3.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0760   -4.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8092   -5.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0062   -5.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5415   -4.6247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2746   -3.8434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2606   -6.0239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3570   -5.6991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6420   -0.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0966   -0.1853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3600    0.5984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1665    0.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7141    0.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4473   -0.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4333    1.5386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8157    1.2139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6016   -1.0057    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5710   -3.4796    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
 12 15  1  0
 11 16  1  0
  6  9  1  6
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 17 22  2  0
 20 23  1  0
 19 24  1  0
  2 17  1  1
  1 25  1  1
  5 26  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1688937

   4-[(3R,3aR,6S,6aR)-3-(3,4-dihydroxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]benzene-1,2-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: 330.34

Molecular Weight (Monoisotopic): 330.1103

AlogP: 2.58

#Rotatable Bonds: 2

Polar Surface Area: 99.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.91

CX Basic pKa: ┄

CX LogP: 1.99

CX LogD: 1.97

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.63

Np Likeness Score: 1.13

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. Nguyen PH, Yang JL, Uddin MN, Park SL, Lim SI, Jung DW, Williams DR, Oh WK..  (2013)  Protein tyrosine phosphatase 1B (PTP1B) inhibitors from Morinda citrifolia (Noni) and their insulin mimetic activity.,  76  (11): [PMID:24224843] [10.1021/np400533h]

3. 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