(S)-2-(5-(3,7-dimethylocta-2,6-dienyl)-2-hydroxy-4-methoxyphenyl)-5,7-dihydroxychroman-4-one

ID: ALA1096940

PubChem CID: 46209782

Max Phase: Preclinical

Molecular Formula: C26H30O6

Molecular Weight: 438.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(O)c([C@@H]2CC(=O)c3c(O)cc(O)cc3O2)cc1C/C=C(\C)CCC=C(C)C

Standard InChI:  InChI=1S/C26H30O6/c1-15(2)6-5-7-16(3)8-9-17-10-19(20(28)13-23(17)31-4)24-14-22(30)26-21(29)11-18(27)12-25(26)32-24/h6,8,10-13,24,27-29H,5,7,9,14H2,1-4H3/b16-8+/t24-/m0/s1

Standard InChI Key:  CZVSHXUUSIQWSO-CECMFTGFSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    7.5991   -7.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5959   -8.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3137   -8.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3110   -7.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0283   -7.6314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.7481   -8.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4688   -8.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4678   -7.6225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7419   -7.2090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7515   -9.7002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1775   -7.2108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8942   -7.6231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6073   -7.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6041   -6.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8829   -5.9731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.4578   -5.9782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3233   -7.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0363   -7.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7522   -7.6132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4652   -7.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7551   -8.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1811   -7.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8941   -7.1932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6101   -7.6031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3231   -7.1881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6130   -8.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0330   -6.3799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3123   -9.6990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8838   -7.2201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3179   -5.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9 12  1  6
 12 13  2  0
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 15 16  1  0
 16 17  2  0
 17 12  1  0
 17 18  1  0
  1  2  2  0
 14 19  1  0
  2  3  1  0
 19 20  1  0
  3  6  2  0
 20 21  2  0
  5  4  2  0
 21 22  1  0
  4  1  1  0
 21 23  1  0
  5  6  1  0
 22 24  1  0
  5 10  1  0
 24 25  1  0
  6  7  1  0
 25 26  2  0
  7  8  1  0
 26 27  1  0
  8  9  1  0
 26 28  1  0
  9 10  1  0
  7 11  2  0
  1 31  1  0
  3 30  1  0
 15 32  1  0
 32 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1096940

   (2S)-2-[5-[(2E)-3,7-dimethylocta-2,6-dienyl]-2-hydroxy-4-methoxyphenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one

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: 438.52

Molecular Weight (Monoisotopic): 438.2042

AlogP: 5.75

#Rotatable Bonds: 7

Polar Surface Area: 96.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.84

CX Basic pKa: ┄

CX LogP: 6.07

CX LogD: 5.93

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.48

Np Likeness Score: 2.33

References

1. Smejkal K, Svacinová J, Slapetová T, Schneiderová K, Dall'acqua S, Innocenti G, Závalová V, Kollár P, Chudík S, Marek R, Julínek O, Urbanová M, Kartal M, Csöllei M, Dolezal K..  (2010)  Cytotoxic activities of several geranyl-substituted flavanones.,  73  (4): [PMID:20192247] [10.1021/np900681y]

2. Heger V, Benesova B, Viskupicova J, Majekova M, Zoofishan Z, Hunyadi A, Horakova L..  (2020)  Phenolic Compounds from Morus nigra Regulate Viability and Apoptosis of Pancreatic β-Cells Possibly via SERCA Activity.,  11  (5): [PMID:32435418] [10.1021/acsmedchemlett.0c00047]

Source

Source(1):

• Scientific Literature