3-(3-hydroxy-4-methoxybenzyl)-5,6,7-trimethoxychroman-4-one

ID: ALA3581080

PubChem CID: 118898652

Max Phase: Preclinical

Molecular Formula: C20H22O7

Molecular Weight: 374.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CC2COc3cc(OC)c(OC)c(OC)c3C2=O)cc1O

Standard InChI:  InChI=1S/C20H22O7/c1-23-14-6-5-11(8-13(14)21)7-12-10-27-15-9-16(24-2)19(25-3)20(26-4)17(15)18(12)22/h5-6,8-9,12,21H,7,10H2,1-4H3

Standard InChI Key:  QPXDJAQCABFFAR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    2.6973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8942    1.4964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1929    0.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4946    1.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7910    0.7351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7858   -0.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4842   -1.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1877   -0.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0845   -1.5172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1250   -0.9193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4800   -2.7104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9091    1.5019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2907    2.9981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9091   -1.5019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9072    2.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9072   -2.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3272    3.6028    0.0000 C   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
 10 11  2  0
  9 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 19 20  1  0
 16 19  1  0
 17 21  1  0
  1 22  1  0
  4 23  1  0
  2 24  1  0
 22 25  1  0
 24 26  1  0
 23 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3581080

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 374.39

Molecular Weight (Monoisotopic): 374.1366

AlogP: 2.86

#Rotatable Bonds: 6

Polar Surface Area: 83.45

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.90

CX Basic pKa: ┄

CX LogP: 2.50

CX LogD: 2.50

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.83

Np Likeness Score: 1.38

References

1. Basavarajappa HD, Lee B, Lee H, Sulaiman RS, An H, Magaña C, Shadmand M, Vayl A, Rajashekhar G, Kim EY, Suh YG, Lee K, Seo SY, Corson TW..  (2015)  Synthesis and Biological Evaluation of Novel Homoisoflavonoids for Retinal Neovascularization.,  58  (12): [PMID:26035340] [10.1021/acs.jmedchem.5b00449]

2. 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]

Source

Source(1):

• Scientific Literature