6,8-Dimethoxy-7-(6'-peroxy-3',7'-dimethyl-2'E,7'-octadienyloxy)coumarin

ID: ALA5290113

Max Phase: Preclinical

Molecular Formula: C21H26O7

Molecular Weight: 390.43

Names and Identifiers

Canonical SMILES:  C=C(C)C(CC/C(C)=C/COc1c(OC)cc2ccc(=O)oc2c1OC)OO

Standard InChI:  InChI=1S/C21H26O7/c1-13(2)16(28-23)8-6-14(3)10-11-26-20-17(24-4)12-15-7-9-18(22)27-19(15)21(20)25-5/h7,9-10,12,16,23H,1,6,8,11H2,2-5H3/b14-10+

Standard InChI Key:  YMKFINXJWAJZIH-GXDHUFHOSA-N

Molfile:  

 
     RDKit          2D

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    1.4306    0.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1452    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8570    0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8570   -0.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1469   -0.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4306   -0.2102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5717    1.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2864    0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2864   -0.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5717   -0.6191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0010   -0.6191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7159   -0.6228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013   -0.2102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7131   -0.6228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4279   -0.2102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1425   -0.6228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4279    0.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8571   -0.2102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5718   -0.6228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2864   -0.2102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0010   -0.6228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2864    0.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5718   -1.4479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7159    1.0308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7159    1.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1469   -1.4434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8616   -1.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2862   -1.8604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  3  7  1  0
  8  7  2  0
  9  8  1  0
 10  9  1  0
  4 10  1  0
  9 11  2  0
  6 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 19 23  1  0
  1 24  1  0
 24 25  1  0
  5 26  1  0
 26 27  1  0
 23 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5290113

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 390.43

Molecular Weight (Monoisotopic): 390.1679

AlogP: 4.35

#Rotatable Bonds: 10

Polar Surface Area: 87.36

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.71

CX Basic pKa: ┄

CX LogP: 3.61

CX LogD: 3.61

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.28

Np Likeness Score: 2.10

References

1. Nhoek P, Ahn S, Pel P, Kim YM, Huh J, Kim HW, Noh M, Chin YW..  (2023)  Alkaloids and Coumarins with Adiponectin-Secretion-Promoting Activities from the Leaves of Orixa japonica.,  86  (1.0): [PMID:36529937] [10.1021/acs.jnatprod.2c00844]

Source

Source(1):

• Scientific Literature