Isobutyric acid-(3R)-5-methoxy-3,4-dihydro-2,2,8-trimethyl-6-oxo-2H,6H-benzo[1,2-b:5,4-b']dipyran-3-yl ester

ID: ALA518222

PubChem CID: 11068391

Max Phase: Preclinical

Molecular Formula: C20H24O6

Molecular Weight: 360.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c2c(cc3oc(C)cc(=O)c13)OC(C)(C)[C@H](OC(=O)C(C)C)C2

Standard InChI:  InChI=1S/C20H24O6/c1-10(2)19(22)25-16-8-12-14(26-20(16,4)5)9-15-17(18(12)23-6)13(21)7-11(3)24-15/h7,9-10,16H,8H2,1-6H3/t16-/m1/s1

Standard InChI Key:  YLXXSWJDIFLXSG-MRXNPFEDSA-N

Molfile:  

     RDKit          2D

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   -2.3315   -7.6845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6172   -8.0960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1882   -6.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5274   -6.8635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5237   -7.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2328   -8.1041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9504   -7.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9542   -6.8700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2404   -6.4541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0464   -7.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3269   -8.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0454   -6.4439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5321   -5.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2431   -5.6229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6605   -8.1149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0442   -5.6210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3309   -5.2107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7563   -5.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7551   -4.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4695   -5.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  2  3  1  0
  2 15  1  0
  5  8  2  0
  2 16  1  0
  6  7  2  0
  1 17  1  6
  7 10  1  0
  8 18  1  0
  9  8  1  0
 18 19  1  0
  9 10  2  0
 14 20  2  0
  3  6  1  0
 12 21  1  0
  5  4  1  0
 17 22  1  0
  5  6  1  0
 22 23  2  0
 22 24  1  0
  1  2  1  0
 24 25  1  0
  1  4  1  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA518222

   [(3R)-5-methoxy-2,2,8-trimethyl-6-oxo-3,4-dihydropyrano[3,2-g]chromen-3-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: 360.41

Molecular Weight (Monoisotopic): 360.1573

AlogP: 3.39

#Rotatable Bonds: 3

Polar Surface Area: 74.97

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.35

CX LogD: 3.35

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.78

Np Likeness Score: 2.39

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