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

ID: ALA464293

PubChem CID: 10904483

Max Phase: Preclinical

Molecular Formula: C19H20O7

Molecular Weight: 360.36

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H20O7/c1-5-13(21)24-17-15-12(26-19(3,4)18(17)23-10(2)20)8-6-11-7-9-14(22)25-16(11)15/h6-9,17-18H,5H2,1-4H3/t17-,18-/m1/s1

Standard InChI Key:  IGMRYMQUDCGCFD-QZTJIDSGSA-N

Molfile:  

     RDKit          2D

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   -3.0221   -0.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3095   -0.9867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5969   -0.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3095    0.6633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5964    0.2454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5906    1.8924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3097    1.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8817    1.4788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8916    0.6464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1828    0.2279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5407    0.6291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5508    1.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1627    1.8846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2501    0.2090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0175   -1.4053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3095   -1.8157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8869   -0.9962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0246   -2.2261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0246   -3.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7395   -1.8115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8884   -1.8211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1740   -2.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5999   -2.2303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5416   -1.8237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9 14  1  0
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 12 15  2  0
  5  8  1  0
  2 16  1  0
  6 10  1  0
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  9  7  1  0
  3 18  1  1
  7  8  2  0
  4 19  1  1
  9 10  2  0
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  3  4  1  0
 20 21  1  0
  4  6  1  0
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  5  6  2  0
 19 23  1  0
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  1  2  1  0
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  1  5  1  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA464293

   Anti-inflammatory agent 57

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: 360.36

Molecular Weight (Monoisotopic): 360.1209

AlogP: 2.89

#Rotatable Bonds: 3

Polar Surface Area: 92.04

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.40

CX LogD: 2.40

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.61

Np Likeness Score: 2.22

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