2'R,3'-Acetyl-3',3'-dimethyl-8-methoxy-6,7-dihydropyrano[3,2-g]coumarin

ID: ALA5273048

Max Phase: Preclinical

Molecular Formula: C17H18O6

Molecular Weight: 318.33

Names and Identifiers

Canonical SMILES:  COc1c2c(cc3ccc(=O)oc13)C[C@@H](C(C)(C)OC(C)=O)O2

Standard InChI:  InChI=1S/C17H18O6/c1-9(18)23-17(2,3)12-8-11-7-10-5-6-13(19)22-14(10)16(20-4)15(11)21-12/h5-7,12H,8H2,1-4H3/t12-/m0/s1

Standard InChI Key:  YYWWBOZMSSQFJL-LBPRGKRZSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    0.0898    1.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8045    1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5164    1.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5164    0.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8063   -0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0898    0.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2311    1.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9457    1.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9457    0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2311   -0.2067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6978    1.2867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6979   -0.0537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1848    0.6165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6604   -0.2067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0099    0.6165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4226   -0.0980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2477   -0.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6604   -0.8127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6604    0.6165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7246    1.0290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0099    1.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8063   -1.0310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5209   -1.4435    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
  1 11  1  0
  6 12  1  0
 12 13  1  0
 13 11  1  0
  9 14  2  0
 13 15  1  6
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 15 20  1  0
 15 21  1  0
  5 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5273048

   ---

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: 318.33

Molecular Weight (Monoisotopic): 318.1103

AlogP: 2.45

#Rotatable Bonds: 3

Polar Surface Area: 74.97

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.02

CX LogD: 2.02

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.64

Np Likeness Score: 2.09

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