2',4-dihydroxy-6-methoxy-5'-methyl-3H,3'H-spiro[2-benzofuran-1,1'-cyclopent[4]ene]-3,3'-dione

ID: ALA408995

Chembl Id: CHEMBL408995

PubChem CID: 14824655

Max Phase: Preclinical

Molecular Formula: C14H12O6

Molecular Weight: 276.24

Molecule Type: Small molecule

Names and Identifiers

Synonyms: talaroflavone | TALAROFLAVONE|CHEMBL408995|CHEBI:219045|NCGC00381160-01|5',7-dihydroxy-5-methoxy-3'-methylspiro[2-benzouran-3,4'-cyclopent-2-ene]-1,1'-dione|NCGC00381160-01_C14H12O6_Spiro[cyclopent-4-ene-1,1'(3'H)-isobenzofuran]-3,3'-dione, 2,4'-dihydroxy-6'-methoxy-5-methyl-

Canonical SMILES:  COc1cc(O)c2c(c1)C1(OC2=O)C(C)=CC(=O)C1O

Standard InChI:  InChI=1S/C14H12O6/c1-6-3-10(16)12(17)14(6)8-4-7(19-2)5-9(15)11(8)13(18)20-14/h3-5,12,15,17H,1-2H3

Standard InChI Key:  ISNKGHIHBITAEG-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA408995

   TALAROFLAVONE

Molecule Features

Natural Product: Yes

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: 276.24

Molecular Weight (Monoisotopic): 276.0634

AlogP: 0.66

#Rotatable Bonds: 1

Polar Surface Area: 93.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.44

CX Basic pKa: ┄

CX LogP: 1.65

CX LogD: 1.65

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.73

Np Likeness Score: 2.35

References

1. Naganuma M, Nishida M, Kuramochi K, Sugawara F, Yoshida H, Mizushina Y..  (2008)  1-deoxyrubralactone, a novel specific inhibitor of families X and Y of eukaryotic DNA polymerases from a fungal strain derived from sea algae.,  16  (6): [PMID:18178092] [10.1016/j.bmc.2007.12.044]

2. Aly AH, Edrada-Ebel R, Indriani ID, Wray V, Müller WE, Totzke F, Zirrgiebel U, Schächtele C, Kubbutat MH, Lin WH, Proksch P, Ebel R..  (2008)  Cytotoxic metabolites from the fungal endophyte Alternaria sp. and their subsequent detection in its host plant Polygonum senegalense.,  71  (6): [PMID:18494522] [10.1021/np070447m]

Source

Source(1):

• Scientific Literature