(E)-5,6,7-Trimethoxy-3-(4'-chloro-3'-hydroxybenzylidene)-4-chromanone

ID: ALA4443803

PubChem CID: 155516487

Max Phase: Preclinical

Molecular Formula: C19H17ClO6

Molecular Weight: 376.79

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc2c(c(OC)c1OC)C(=O)/C(=C/c1ccc(Cl)c(O)c1)CO2

Standard InChI:  InChI=1S/C19H17ClO6/c1-23-15-8-14-16(19(25-3)18(15)24-2)17(22)11(9-26-14)6-10-4-5-12(20)13(21)7-10/h4-8,21H,9H2,1-3H3/b11-6+

Standard InChI Key:  CUXKMALDRBZKQY-IZZDOVSWSA-N

Molfile:  

 
     RDKit          2D

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    6.2920   -4.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4318   -4.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4307   -4.9647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1455   -5.3776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1437   -3.7246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8591   -4.1338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8579   -4.9622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5709   -5.3752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2907   -4.1358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5732   -3.7183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5685   -6.2002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7173   -3.7251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1472   -6.2026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0049   -5.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7209   -4.9720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4323   -5.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1477   -4.9801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1510   -4.1543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4330   -3.7395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7205   -4.1511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7159   -5.3767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0018   -4.9636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8605   -5.3954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7171   -2.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4336   -6.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8664   -3.7433    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
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  3 21  1  0
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 18 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4443803

   ---

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: 376.79

Molecular Weight (Monoisotopic): 376.0714

AlogP: 3.73

#Rotatable Bonds: 4

Polar Surface Area: 74.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.82

CX Basic pKa: ┄

CX LogP: 3.19

CX LogD: 3.05

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.82

Np Likeness Score: 0.64

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