5-(2,3-Dihydroxy-3-methylbutoxy)-6,7-methylenedioxycoumarin

ID: ALA611815

Cas Number: 52146-70-0

PubChem CID: 179597

Max Phase: Preclinical

Molecular Formula: C15H16O7

Molecular Weight: 308.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(O)C(O)COc1c2c(cc3oc(=O)ccc13)OCO2

Standard InChI:  InChI=1S/C15H16O7/c1-15(2,18)11(16)6-19-13-8-3-4-12(17)22-9(8)5-10-14(13)21-7-20-10/h3-5,11,16,18H,6-7H2,1-2H3

Standard InChI Key:  RDPGEFVUMRTSBB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   14.6467   -6.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6449   -4.5131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9330   -5.7513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9343   -4.9237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1476   -4.6668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6601   -5.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1456   -6.0058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3591   -4.9217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3626   -5.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0805   -6.1640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7997   -5.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7963   -4.9158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0737   -4.5006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5142   -6.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6430   -3.6895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9289   -3.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9270   -2.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2129   -2.0454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6394   -2.0422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0463   -1.3228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0521   -1.4518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3500   -2.4502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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  1  0
  3  4  2  0
 17 19  1  0
  3  1  1  0
 19 20  1  0
  1  9  2  0
 19 21  1  0
 19 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA611815

   Sabandinol

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: 308.29

Molecular Weight (Monoisotopic): 308.0896

AlogP: 1.03

#Rotatable Bonds: 4

Polar Surface Area: 98.36

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.20

CX Basic pKa: ┄

CX LogP: 0.63

CX LogD: 0.63

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.81

Np Likeness Score: 1.57

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. PubChem BioAssay data set, 

3. 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]

4. 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(2):

• Scientific Literature
• PubChem BioAssays