2-Methylbut-(2Z)-enoic 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: ALA458524

PubChem CID: 10904780

Max Phase: Preclinical

Molecular Formula: C21H24O6

Molecular Weight: 372.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C=C(/C)C(=O)O[C@@H]1Cc2c(cc3oc(C)cc(=O)c3c2OC)OC1(C)C

Standard InChI:  InChI=1S/C21H24O6/c1-7-11(2)20(23)26-17-9-13-15(27-21(17,4)5)10-16-18(19(13)24-6)14(22)8-12(3)25-16/h7-8,10,17H,9H2,1-6H3/b11-7-/t17-/m1/s1

Standard InChI Key:  QNOQNIIIQHXDAV-CGICMKJESA-N

Molfile:  

     RDKit          2D

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   11.1465   -1.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8609   -1.8578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8609   -0.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5753   -0.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5718   -1.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2828   -1.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2898   -0.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0055   -0.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0017   -1.4503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7109   -1.8658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4285   -1.4569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4323   -0.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7185   -0.2158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4316   -1.0349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1511   -2.2734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4326   -0.2058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2922    0.6226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0102    1.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7212    0.6153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1385   -1.8767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4338    0.6171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1471    1.0276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7218    1.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7229    1.8526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0086    0.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0074   -0.2037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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  2  0
  9 14  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA458524

   [(3R)-5-methoxy-2,2,8-trimethyl-6-oxo-3,4-dihydropyrano[3,2-g]chromen-3-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: 372.42

Molecular Weight (Monoisotopic): 372.1573

AlogP: 3.70

#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: 3.88

CX LogD: 3.88

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.60

Np Likeness Score: 2.78

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