5-(3-methyl-2-butenyloxy)-6,7-methylenedioxycoumarin

ID: ALA595800

Cas Number: 160177-41-3

PubChem CID: 46226618

Max Phase: Preclinical

Molecular Formula: C15H14O5

Molecular Weight: 274.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)=CCOc1c2c(cc3oc(=O)ccc13)OCO2

Standard InChI:  InChI=1S/C15H14O5/c1-9(2)5-6-17-14-10-3-4-13(16)20-11(10)7-12-15(14)19-8-18-12/h3-5,7H,6,8H2,1-2H3

Standard InChI Key:  LVDCFTVFEPEBSA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    3.3058   -5.1117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3040   -3.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5914   -4.6990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5927   -3.8707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8052   -3.6136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3173   -4.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8033   -4.9538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0188   -3.8686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0223   -4.7011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7409   -5.1122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4608   -4.6952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4574   -3.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7341   -3.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1759   -5.1056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3021   -2.6354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0152   -2.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7301   -2.6323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4431   -2.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1580   -2.6291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4413   -1.3940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  2  0
  8  2  2  0
  2  4  1  0
  8 13  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
  4  5  1  0
 11 14  2  0
  5  6  1  0
  2 15  1  0
  6  7  1  0
 15 16  1  0
  7  3  1  0
 16 17  1  0
  8  9  1  0
 17 18  2  0
  3  4  2  0
 18 19  1  0
  3  1  1  0
 18 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA595800

   9-[(3-Methylbut-2-en-1-yl)oxy]-2H,6H-[1,3]dioxolo[4,5-g][1]benzopyran-6-one

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: 274.27

Molecular Weight (Monoisotopic): 274.0841

AlogP: 2.87

#Rotatable Bonds: 3

Polar Surface Area: 57.90

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.61

CX LogD: 2.61

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.64

Np Likeness Score: 1.45

References

1. Riveiro ME, Maes D, Vázquez R, Vermeulen M, Mangelinckx S, Jacobs J, Debenedetti S, Shayo C, De Kimpe N, Davio C..  (2009)  Toward establishing structure-activity relationships for oxygenated coumarins as differentiation inducers of promonocytic leukemic cells.,  17  (18): [PMID:19716307] [10.1016/j.bmc.2009.08.002]

2. Vianna DR, Hamerski L, Figueiró F, Bernardi A, Visentin LC, Pires EN, Teixeira HF, Salbego CG, Eifler-Lima VL, Battastini AM, von Poser GL, Pinto AC..  (2012)  Selective cytotoxicity and apoptosis induction in glioma cell lines by 5-oxygenated-6,7-methylenedioxycoumarins from Pterocaulon species.,  57  [PMID:23069682] [10.1016/j.ejmech.2012.09.007]

3. Garro Hugo A, Manzur Jimena M, Ciuffo Gladys M, Tonn Carlos E, Pungitore Carlos R..  (2014)  Inhibition of reverse transcriptase and Taq DNA polymerase by compounds possessing the coumarin framework.,  24  (3): [PMID:24418776] [10.1016/j.bmcl.2013.12.104]

Source

Source(1):

• Scientific Literature