1-(4-hydroxy-3,5-dimethoxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)propane

ID: ALA2409062

PubChem CID: 73349087

Max Phase: Preclinical

Molecular Formula: C18H22O5

Molecular Weight: 318.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(CCCc2cc(OC)c(O)c(OC)c2)ccc1O

Standard InChI:  InChI=1S/C18H22O5/c1-21-15-9-12(7-8-14(15)19)5-4-6-13-10-16(22-2)18(20)17(11-13)23-3/h7-11,19-20H,4-6H2,1-3H3

Standard InChI Key:  FHKKEKQKYAGUKW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   25.0343  -14.2141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0332  -15.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7413  -15.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4509  -15.0332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4481  -14.2105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7395  -13.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3265  -13.8057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1593  -15.4407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8663  -15.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5747  -15.4385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2817  -15.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9888  -15.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6954  -15.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6945  -14.2105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9812  -13.8032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2776  -14.2146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4011  -13.7999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.4035  -15.4364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.4044  -16.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7370  -12.9881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4435  -12.5774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3252  -15.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6178  -15.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  4  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 14 17  1  0
 13 18  1  0
 18 19  1  0
  6 20  1  0
 20 21  1  0
  2 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2409062

   4-[3-(4-Hydroxy-3-methoxyphenyl)propyl]-2,6-dimethoxyphenol

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: 318.37

Molecular Weight (Monoisotopic): 318.1467

AlogP: 3.30

#Rotatable Bonds: 7

Polar Surface Area: 68.15

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.60

CX Basic pKa: ┄

CX LogP: 3.87

CX LogD: 3.87

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.82

Np Likeness Score: 0.65

References

1. Moosophon P, Kanokmedhakul S, Kanokmedhakul K, Buayairaksa M, Noichan J, Poopasit K..  (2013)  Antiplasmodial and cytotoxic flavans and diarylpropanes from the stems of Combretum griffithii.,  76  (7): [PMID:23795891] [10.1021/np400266h]

2. Jang HY, Park HJ, Damodar K, Kim JK, Jun JG..  (2016)  Dihydrostilbenes and diarylpropanes: Synthesis and in vitro pharmacological evaluation as potent nitric oxide production inhibition agents.,  26  (22): [PMID:27777005] [10.1016/j.bmcl.2016.10.034]

Source

Source(1):

• Scientific Literature