2-methylbut-(2Z)-enoic acid(9R,10R)-10-hydroxy-8,8-dimethyl-9,10-dihydro-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one-9-yl ester

ID: ALA463449

PubChem CID: 11244847

Max Phase: Preclinical

Molecular Formula: C19H20O6

Molecular Weight: 344.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C=C(/C)C(=O)O[C@@H]1[C@H](O)c2c(ccc3ccc(=O)oc23)OC1(C)C

Standard InChI:  InChI=1S/C19H20O6/c1-5-10(2)18(22)24-17-15(21)14-12(25-19(17,3)4)8-6-11-7-9-13(20)23-16(11)14/h5-9,15,17,21H,1-4H3/b10-5-/t15-,17-/m1/s1

Standard InChI Key:  KJWFOHVSTFGWGZ-YCDQCDSPSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   17.9654  -19.2033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9654  -20.0257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6765  -20.4381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3875  -20.0257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6765  -18.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3882  -19.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3970  -17.5529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6762  -17.9654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1025  -17.9722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0957  -18.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8053  -19.2200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5284  -18.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5354  -17.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8230  -17.5607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2388  -19.2362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2436  -19.6176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9684  -20.8525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6765  -21.2607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0987  -20.4422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9621  -21.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9621  -22.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2431  -21.2607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2441  -22.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6757  -22.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3894  -22.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
  2  3  1  0
 12 15  2  0
  5  8  1  0
  2 16  1  0
  6 10  1  0
  2 17  1  0
  9  7  1  0
  3 18  1  1
  7  8  2  0
  4 19  1  1
  9 10  2  0
 18 20  1  0
  3  4  1  0
 20 21  1  0
  4  6  1  0
 20 22  2  0
  5  6  2  0
 21 23  1  0
 21 24  2  0
  1  2  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA463449

   [(9R,10R)-10-hydroxy-8,8-dimethyl-2-oxo-9,10-dihydropyrano[2,3-f]chromen-9-yl] (Z)-2-methylbut-2-enoate

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: 344.36

Molecular Weight (Monoisotopic): 344.1260

AlogP: 2.88

#Rotatable Bonds: 2

Polar Surface Area: 85.97

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.82

CX Basic pKa: ┄

CX LogP: 3.03

CX LogD: 3.03

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.51

Np Likeness Score: 2.64

References

1. Valencia-Islas N, Abbas H, Bye R, Toscano R, Mata R..  (2002)  Phytotoxic compounds from Prionosciadium watsoni.,  65  (6): [PMID:12088423] [10.1021/np010448t]

Source

Source(1):

• Scientific Literature