(3E,5E)-6-{3-[1-(1,1-Dimethyl-allyloxy)-1-methyl-ethyl]-2,3-dihydro-benzo[1,4]dioxin-6-yl}-4-methoxy-2-[1-methoxy-meth-(E)-ylidene]-3-methyl-hexa-3,5-dienoic acid methyl ester

ID: ALA3350301

PubChem CID: 6476322

Max Phase: Preclinical

Molecular Formula: C27H36O7

Molecular Weight: 472.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(C)(C)OC(C)(C)[C@@H]1COc2ccc(/C=C/C(OC)=C(C)\C(=C/OC)C(=O)OC)cc2O1

Standard InChI:  InChI=1S/C27H36O7/c1-10-26(3,4)34-27(5,6)24-17-32-22-14-12-19(15-23(22)33-24)11-13-21(30-8)18(2)20(16-29-7)25(28)31-9/h10-16,24H,1,17H2,2-9H3/b13-11+,20-16+,21-18+/t24-/m0/s1

Standard InChI Key:  IKBKPRBEIXBOIF-GHJTYKTFSA-N

Molfile:  

     RDKit          2D

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    2.2995  -12.5644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2966  -11.7338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5813  -11.3247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8682  -12.5648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8724  -11.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5536  -12.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1575  -12.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2613  -11.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9792  -10.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8469  -10.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6728  -12.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9798  -10.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7256  -11.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4385  -11.3133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1545  -11.7231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1576  -12.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8674  -11.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4447  -12.9632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8736  -12.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5853  -12.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3021  -12.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4478  -13.7882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7287  -12.5534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7349  -14.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4354  -10.4883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1483  -10.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0
  4  6  1  0
 15 17  1  0
  5 10  1  0
 15 18  1  0
  6  7  1  0
 16 19  2  0
  7  8  1  0
  3 20  1  0
  8  9  1  0
 20 21  2  0
  9 10  1  0
 21 22  1  0
  5  6  2  0
 22 23  2  0
  8 11  1  1
 22 33  1  0
  1  2  2  0
 23 24  1  0
 11 12  1  0
 23 25  1  0
  5  1  1  0
 24 26  1  0
 11 13  1  0
 24 27  2  0
  2  3  1  0
 27 28  1  0
 11 14  1  0
 28 29  1  0
 26 30  1  0
 12 15  1  0
 26 31  2  0
  3  4  2  0
 30 32  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3350301

   methyl (2E,3E,5E)-4-methoxy-2-(methoxymethylidene)-3-methyl-6-[(3S)-3-[2-(2-methylbut-3-en-2-yloxy)propan-2-yl]-2,3-dihydro-1,4-benzodioxin-6-yl]hexa-3,5-dienoate

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: 472.58

Molecular Weight (Monoisotopic): 472.2461

AlogP: 5.22

#Rotatable Bonds: 10

Polar Surface Area: 72.45

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.44

CX LogD: 4.44

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.15

Np Likeness Score: 1.81

References

1. Aiba Y, Hasegawa D, Marunouchi T, Nagasawa K, Uchiro H, Kobayashi S..  (2001)  Total synthesis and antifungal activity of 9-methoxystrobilurin L as the originally proposed 1,4-benzodioxan structure.,  11  (20): [PMID:11591523] [10.1016/s0960-894x(01)00561-3]

Source

Source(1):

• Scientific Literature