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

ID: ALA518224

PubChem CID: 11034942

Max Phase: Preclinical

Molecular Formula: C18H20O6

Molecular Weight: 332.35

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H20O6/c1-9(2)17(21)23-15-13-11(24-18(3,4)16(15)20)7-5-10-6-8-12(19)22-14(10)13/h5-9,15-16,20H,1-4H3/t15-,16-/m1/s1

Standard InChI Key:  JHCPPFWOQPOFRF-HZPDHXFCSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    3.8764    0.4643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8764   -0.3607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5891   -0.7670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3017   -0.3607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5891    0.8831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3022    0.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3081    2.1124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5889    1.7059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0171    1.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0070    0.8662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7161    0.4477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4396    0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4497    1.6772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7361    2.1045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1491    0.4288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1592    0.0539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8811   -1.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5891   -1.5962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0118   -0.7765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0104   -1.6016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7248   -2.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2988   -2.0107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4406   -1.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7233   -2.8383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
 19 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  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA518224

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

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: 332.35

Molecular Weight (Monoisotopic): 332.1260

AlogP: 2.57

#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: 2.50

CX LogD: 2.50

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.67

Np Likeness Score: 2.13

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