6-Hydroxy-3-[1-(4-hydroxy-phenyl)-meth-(E)-ylidene]-3H-benzofuran-2-one

ID: ALA195416

Chembl Id: CHEMBL195416

PubChem CID: 9837937

Max Phase: Preclinical

Molecular Formula: C15H10O4

Molecular Weight: 254.24

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Isoaurostatin | CHEMBL195416|SCHEMBL15426107|BDBM50164888|6-Hydroxy-3-[1-(4-hydroxy-phenyl)-meth-(E)-ylidene]-3H-benzofuran-2-one

Canonical SMILES:  O=C1Oc2cc(O)ccc2/C1=C\c1ccc(O)cc1

Standard InChI:  InChI=1S/C15H10O4/c16-10-3-1-9(2-4-10)7-13-12-6-5-11(17)8-14(12)19-15(13)18/h1-8,16-17H/b13-7+

Standard InChI Key:  DJGNNZVFOBIPMK-NTUHNPAUSA-N

Alternative Forms

1. Parent:

   

   ALA195416

   ISOAUROSTATIN

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: 254.24

Molecular Weight (Monoisotopic): 254.0579

AlogP: 2.56

#Rotatable Bonds: 1

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.50

CX Basic pKa: ┄

CX LogP: 3.26

CX LogD: 3.23

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.47

Np Likeness Score: 0.61

References

1. Suzuki K, Okawara T, Higashijima T, Yokomizo K, Mizushima T, Otsuka M..  (2005)  Inhibitory activities against topoisomerase I and II by isoaurostatin derivatives and their structure-activity relationships.,  15  (8): [PMID:15808469] [10.1016/j.bmcl.2005.02.052]

2. Rizzi E, Dallavalle S, Merlini L, Beretta GL, Pratesi G, Zunino F..  (2005)  A new synthesis of isoaurones: cytotoxic activity of compounds related to the alleged structure of isoaurostatin.,  15  (19): [PMID:16040242] [10.1016/j.bmcl.2005.06.045]

3. Suzuki K, Yahara S, Maehata K, Uyeda M..  (2001)  Isoaurostatin, a novel topoisomerase inhibitor produced by Thermomonospora alba.,  64  (2): [PMID:11430001] [10.1021/np0004606]

4. Alsayari A, Muhsinah AB, Hassan MZ, Ahsan MJ, Alshehri JA, Begum N..  (2019)  Aurone: A biologically attractive scaffold as anticancer agent.,  166  [PMID:30739824] [10.1016/j.ejmech.2019.01.078]

Source

Source(1):

• Scientific Literature