7-(7'-Peroxy-3',7'-dimethylocta-2',5'-dienyloxy)-6,8-dimethoxycoumarin

ID: ALA5284439

Max Phase: Preclinical

Molecular Formula: C21H26O7

Molecular Weight: 390.43

Names and Identifiers

Canonical SMILES:  COc1cc2ccc(=O)oc2c(OC)c1OC/C=C(\C)C/C=C/C(C)(C)OO

Standard InChI:  InChI=1S/C21H26O7/c1-14(7-6-11-21(2,3)28-23)10-12-26-19-16(24-4)13-15-8-9-17(22)27-18(15)20(19)25-5/h6,8-11,13,23H,7,12H2,1-5H3/b11-6+,14-10+

Standard InChI Key:  BZZXVPRMSSDNIO-PPGMXFKZSA-N

Molfile:  

 
     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    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   -0.2064    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   -0.2101    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   -0.2101    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   -0.2101    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   -0.2101    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   -0.2101    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
    0.7159    1.0309    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
    2.8617   -1.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0010    0.2024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7154   -0.2101    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  2  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
  1 23  1  0
 23 24  1  0
  5 25  1  0
 25 26  1  0
 20 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5284439

   ---

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: 9

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: 11.70

CX Basic pKa: ┄

CX LogP: 3.51

CX LogD: 3.51

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.29

Np Likeness Score: 2.20

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