2-[(2E,6E)-3,7-dimethyl-8-(4-methylfuran-2-yl)octa-2,6-dienyl]-5-methylbenzene-1,4-diol

ID: ALA1099278

PubChem CID: 5458654

Max Phase: Preclinical

Molecular Formula: C22H28O3

Molecular Weight: 340.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C(=C\Cc1cc(O)c(C)cc1O)CC/C=C(\C)Cc1cc(C)co1

Standard InChI:  InChI=1S/C22H28O3/c1-15(8-9-19-13-21(23)18(4)12-22(19)24)6-5-7-16(2)10-20-11-17(3)14-25-20/h7-8,11-14,23-24H,5-6,9-10H2,1-4H3/b15-8+,16-7+

Standard InChI Key:  ADYURFIGBFVBDI-ANSQBLEFSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   -0.4488  -23.8735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3116  -23.5535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2441  -22.7311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5615  -22.5420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9857  -23.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9985  -21.8423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0170  -23.9814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7402  -23.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4456  -24.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7581  -22.7596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1688  -23.6154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8742  -24.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5974  -23.6463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3028  -24.0742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6153  -22.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0260  -23.6773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7314  -24.1051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7085  -24.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4131  -25.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1373  -24.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1526  -24.1316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4474  -23.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3948  -26.1825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4616  -22.8827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8432  -25.3877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  6  1  0
 12 13  1  0
 13 14  2  0
  2  7  1  0
 13 15  1  0
  2  3  2  0
 14 16  1  0
  7  8  1  0
 16 17  1  0
  3  4  1  0
 17 18  2  0
  8  9  2  0
 18 19  1  0
  4  5  2  0
 19 20  2  0
  8 10  1  0
 20 21  1  0
  5  1  1  0
 21 22  2  0
 22 17  1  0
  9 11  1  0
 19 23  1  0
  1  2  1  0
 22 24  1  0
 11 12  1  0
 20 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1099278

   Furanoterpene Coll FN30

Molecule Features

Natural Product: No

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: 340.46

Molecular Weight (Monoisotopic): 340.2038

AlogP: 5.77

#Rotatable Bonds: 7

Polar Surface Area: 53.60

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.75

CX Basic pKa: ┄

CX LogP: 6.26

CX LogD: 6.26

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.50

Np Likeness Score: 2.20

References

1. Cheng SY, Huang KJ, Wang SK, Wen ZH, Chen PW, Duh CY..  (2010)  Antiviral and anti-inflammatory metabolites from the soft coral Sinularia capillosa.,  73  (4): [PMID:20155971] [10.1021/np9008078]

Source

Source(1):

• Scientific Literature