3-acetoxymethyl-5-[(E)-2-formylethen-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-2,3-dihydrobenzofuran

ID: ALA4526707

PubChem CID: 10644549

Max Phase: Preclinical

Molecular Formula: C22H22O7

Molecular Weight: 398.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc([C@@H]2Oc3c(OC)cc(/C=C/C=O)cc3[C@H]2COC(C)=O)ccc1O

Standard InChI:  InChI=1S/C22H22O7/c1-13(24)28-12-17-16-9-14(5-4-8-23)10-20(27-3)22(16)29-21(17)15-6-7-18(25)19(11-15)26-2/h4-11,17,21,25H,12H2,1-3H3/b5-4+/t17-,21+/m1/s1

Standard InChI Key:  RATHWHQMVNHBER-FLWKIERCSA-N

Molfile:  

 
     RDKit          2D

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    9.4538  -21.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4509  -20.3049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7355  -19.8957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0225  -21.1359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0192  -20.3115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2341  -20.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7523  -20.7288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2395  -21.3937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9318  -20.7328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171  -20.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6928  -20.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2824  -20.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7023  -21.4533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5251  -21.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4574  -20.7426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2777  -19.3084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6876  -18.5925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9761  -19.2763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5256  -18.6610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7371  -22.3738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0225  -22.7861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2676  -17.8775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8172  -17.2622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4599  -17.7092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1639  -19.8897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8783  -20.3022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5928  -19.8897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3073  -20.3022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0
  2  3  1  0
  3  4  2  0
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  6  7  1  0
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  8 10  1  1
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 12 17  1  0
 17 18  1  0
  7 19  1  6
 19 20  1  0
  1 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 23 25  2  0
  3 26  1  0
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 27 28  1  0
 28 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4526707

   [(2R,3S)-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-[(E)-3-oxoprop-1-enyl]-2,3-dihydro-1-benzofuran-3-yl]methyl acetate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 398.41

Molecular Weight (Monoisotopic): 398.1366

AlogP: 3.40

#Rotatable Bonds: 7

Polar Surface Area: 91.29

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.91

CX Basic pKa: ┄

CX LogP: 2.44

CX LogD: 2.43

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.43

Np Likeness Score: 1.91

References

1. Odonbayar B, Murata T, Suganuma K, Ishikawa Y, Buyankhishig B, Batkhuu J, Sasaki K..  (2019)  Acylated Lignans Isolated from Brachanthemum gobicum and Their Trypanocidal Activity.,  82  (4): [PMID:30896183] [10.1021/acs.jnatprod.8b00670]

Source

Source(1):

• Scientific Literature