4-((5-acetyl-6-hydroxy-7-methoxybenzofuran-4-yloxy)methyl)benzoic acid

Names and Identifiers

Canonical SMILES: COc1c(O)c(C(C)=O)c(OCc2ccc(C(=O)O)cc2)c2ccoc12

Standard InChI: InChI=1S/C19H16O7/c1-10(20)14-15(21)18(24-2)17-13(7-8-25-17)16(14)26-9-11-3-5-12(6-4-11)19(22)23/h3-8,21H,9H2,1-2H3,(H,22,23)

Standard InChI Key: SLKFEHLKZBEQMU-UHFFFAOYSA-N

Molfile:

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   10.4888  -15.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2062  -16.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9228  -15.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9169  -14.9843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4864  -14.9913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2036  -14.5757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0300  -13.7651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2054  -13.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8696  -14.4376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6291  -14.5680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6248  -13.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3371  -13.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0559  -13.7397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7677  -13.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7590  -12.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0421  -12.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3333  -12.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6400  -16.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6457  -17.0410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3517  -15.7986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2101  -17.0533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7755  -16.2313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7778  -17.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4711  -12.0813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1883  -12.4890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4656  -11.2563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0
 12 13  2  0
  2  3  2  0
 13 14  1  0
 14 15  2  0
  3  4  1  0
 15 16  1  0
  6  7  1  0
 16 17  2  0
 17 12  1  0
  7  8  2  0
  3 18  1  0
  8  9  1  0
 18 19  1  0
  9  5  1  0
 18 20  2  0
  4  6  2  0
  2 21  1  0
  4 10  1  0
  1 22  1  0
  5  6  1  0
 22 23  1  0
 10 11  1  0
  1  2  1  0
 11 12  1  0
 24 25  1  0
 24 26  2  0
 15 24  1  0
M  END

Alternative Forms

Parent:

ALA381242
4-[(5-Acetyl-6-hydroxy-7-methoxy-1-benzofuran-4-yl)oxymethyl]benzoic acid

Associated Targets(non-human)

Kcna3 Voltage-gated potassium channel subunit Kv1.3 (114 Activities)

Discover Target: Kcna3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

Drug Indications

MESH ID	MESH Heading	EFO IDs	EFO Terms	Max Phase for Indication	References

Mechanisms of Action

Mechanism of Action	Action Type	target ID	Target Name	Target Type	Target Organism	Binding Site Name	References

Calculated Properties

Molecular Weight: 356.33	Molecular Weight (Monoisotopic): 356.0896	AlogP: 3.63	#Rotatable Bonds: 6
Polar Surface Area: 106.20	Molecular Species: ACID	HBA: 6	HBD: 2
#RO5 Violations: ┄	HBA (Lipinski): 7	HBD (Lipinski): 2	#RO5 Violations (Lipinski): ┄
CX Acidic pKa: 4.06	CX Basic pKa: ┄	CX LogP: 3.10	CX LogD: -0.05
Aromatic Rings: 3	Heavy Atoms: 26	QED Weighted: 0.65	Np Likeness Score: 0.77

References

1. Harvey AJ, Baell JB, Toovey N, Homerick D, Wulff H.. (2006) A new class of blockers of the voltage-gated potassium channel Kv1.3 via modification of the 4- or 7-position of khellinone., 49 (4): [PMID:16480279] [10.1021/jm050839v]

Source

Source(1):

Scientific Literature