7-((2'E,5'E)-7'-methoxy-3',7'-dimethylocta-2',5'-dienyloxy)coumarin

ID: ALA5266890

Max Phase: Preclinical

Molecular Formula: C20H24O4

Molecular Weight: 328.41

Names and Identifiers

Canonical SMILES:  COC(C)(C)/C=C/C/C(C)=C/COc1ccc2ccc(=O)oc2c1

Standard InChI:  InChI=1S/C20H24O4/c1-15(6-5-12-20(2,3)22-4)11-13-23-17-9-7-16-8-10-19(21)24-18(16)14-17/h5,7-12,14H,6,13H2,1-4H3/b12-5+,15-11+

Standard InChI Key:  HSQQMAPGYSIBOS-SZCVXIABSA-N

Molfile:  

 
     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    1.7880    0.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5025    0.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2144    0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2144   -0.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5043   -0.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7880   -0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9291    0.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6437    0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6437   -0.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9291   -0.8233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3583   -0.8233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0733   -0.8270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3585   -0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3558   -0.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0705   -0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852   -0.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0705    0.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4998   -0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2144   -0.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9291   -0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6437   -0.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9291    0.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6437   -0.0018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3583   -0.4144    0.0000 C   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
 20 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5266890

   ---

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: 328.41

Molecular Weight (Monoisotopic): 328.1675

AlogP: 4.49

#Rotatable Bonds: 7

Polar Surface Area: 48.67

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.02

CX LogD: 4.02

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.55

Np Likeness Score: 1.76

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