5,6,7-Trimethoxy-3(R)-(3'hydroxy-4'-methoxybenzyl)-4-chromanone

ID: ALA4474477

PubChem CID: 155537067

Max Phase: Preclinical

Molecular Formula: C20H22O7

Molecular Weight: 374.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(C[C@@H]2COc3cc(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/t12-/m1/s1

Standard InChI Key:  QPXDJAQCABFFAR-GFCCVEGCSA-N

Molfile:  

 
     RDKit          2D

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    2.8610  -28.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8598  -29.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5747  -29.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5729  -27.8077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2882  -28.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2871  -29.0453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0001  -29.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7199  -28.2189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0024  -27.8013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9978  -30.2833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1465  -27.8082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5764  -30.2857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4341  -29.4651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1500  -29.0551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8614  -29.4725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5769  -29.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5802  -28.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8621  -27.8224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1497  -28.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2956  -27.8264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1451  -29.4598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4309  -29.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2897  -29.4785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1463  -26.9832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8628  -30.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2974  -27.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
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  7  8  1  0
  1  8  1  0
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  8 11  2  0
  2 12  1  0
  4 13  1  0
  1 14  1  1
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 15 16  2  0
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 18 19  1  0
 19 20  2  0
 20 15  1  0
 18 21  1  0
  3 22  1  0
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 17 24  1  0
 12 25  1  0
 13 26  1  0
 21 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4474477

   ---

Molecule Features

Natural Product: No

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: 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. 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