7-(6'R-hydroxy-3',7'-dimethyl-2'E,7'-octadienyloxy)coumarin

ID: ALA5282703

Max Phase: Preclinical

Molecular Formula: C19H22O6

Molecular Weight: 346.38

Names and Identifiers

Canonical SMILES:  C=C(C)C(O)CC/C(C)=C/COc1c(O)cc2ccc(=O)oc2c1O

Standard InChI:  InChI=1S/C19H22O6/c1-11(2)14(20)6-4-12(3)8-9-24-19-15(21)10-13-5-7-16(22)25-18(13)17(19)23/h5,7-8,10,14,20-21,23H,1,4,6,9H2,2-3H3/b12-8+

Standard InChI Key:  RPYLOXBSVFYWKB-XYOKQWHBSA-N

Molfile:  

 
     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    1.4306    0.8266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1452    1.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8571    0.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8571    0.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1469   -0.4099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4306   -0.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5717    1.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2864    0.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2864    0.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5717   -0.4107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0010   -0.4107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7160   -0.4144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013   -0.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7131   -0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4278   -0.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1425   -0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4278    0.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8571   -0.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5717   -0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2864   -0.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0010   -0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2864    0.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5717   -1.2396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7160    1.2392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1469   -1.2351    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
  5 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5282703

   ---

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: 346.38

Molecular Weight (Monoisotopic): 346.1416

AlogP: 3.25

#Rotatable Bonds: 7

Polar Surface Area: 100.13

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.91

CX Basic pKa: ┄

CX LogP: 3.52

CX LogD: 3.52

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.53

Np Likeness Score: 2.38

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