3,5,7-trihydroxy-3-(4-methoxybenzyl)chroman-4-one

ID: ALA4528720

PubChem CID: 12309804

Max Phase: Preclinical

Molecular Formula: C17H16O6

Molecular Weight: 316.31

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(CC2(O)COc3cc(O)cc(O)c3C2=O)cc1

Standard InChI:  InChI=1S/C17H16O6/c1-22-12-4-2-10(3-5-12)8-17(21)9-23-14-7-11(18)6-13(19)15(14)16(17)20/h2-7,18-19,21H,8-9H2,1H3

Standard InChI Key:  BLSFQQNRFOVLGQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    4.4023  -18.5106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4012  -19.3301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1092  -19.7391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1074  -18.1017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8161  -18.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8149  -19.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5211  -19.7367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2330  -19.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2341  -18.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5234  -18.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6945  -18.1022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5188  -20.5539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9395  -19.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6484  -19.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3522  -19.7478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0605  -19.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0632  -18.5238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3517  -18.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6462  -18.5217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7715  -18.1163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1109  -20.5563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7727  -17.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2268  -20.1450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  1 11  1  0
  7 12  2  0
  8 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 17 20  1  0
  3 21  1  0
 20 22  1  0
  8 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4528720

   3,5,7-Trihydroxy-3-(4-methoxybenzyl)chroman-4-one

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 316.31

Molecular Weight (Monoisotopic): 316.0947

AlogP: 1.66

#Rotatable Bonds: 3

Polar Surface Area: 96.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.76

CX Basic pKa: ┄

CX LogP: 2.57

CX LogD: 2.41

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.80

Np Likeness Score: 1.67

References

1. Schwikkard S, Whitmore H, Sishtla K, Sulaiman RS, Shetty T, Basavarajappa HD, Waller C, Alqahtani A, Frankemoelle L, Chapman A, Crouch N, Wetschnig W, Knirsch W, Andriantiana J, Mas-Claret E, Langat MK, Mulholland D, Corson TW..  (2019)  The Antiangiogenic Activity of Naturally Occurring and Synthetic Homoisoflavonoids from the Hyacinthaceae ( sensu APGII).,  82  (5): [PMID:30951308] [10.1021/acs.jnatprod.8b00989]

2. Kishore N, Kumar P, Shanker K, Verma AK..  (2019)  Human disorders associated with inflammation and the evolving role of natural products to overcome.,  179  [PMID:31255927] [10.1016/j.ejmech.2019.06.034]

Source

Source(1):

• Scientific Literature