3'-methoxy-4'-O-(3-methyl-2-butenyl)-3'',3''-dimethylpyrano-(6,7)-isoflavone

ID: ALA1773675

Cas Number: 1292766-23-4

PubChem CID: 52951634

Max Phase: Preclinical

Molecular Formula: C26H26O5

Molecular Weight: 418.49

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Pierreione D | Pierreione D|CHEBI:68050|CHEMBL1773675|DTXSID601111022|Q27136546|3'-methoxy-4'-O-(3-methyl-2-butenyl)-3'',3''-dimethylpyrano-(6,7)-isoflavone|1292766-23-4|2H,6H-Benzo[1,2-b:5,4-b']dipyran-6-one, 7-[3-methoxy-4-[(3-methyl-2-buten-1-yl)oxy]phenyl]-2,2-dimethyl-|7-{3-methoxy-4-[(3-methylbut-2-en-1-yl)oxy]phenyl}-2,2-dimethyl-2H,6H-pyrano[3,2-g]chromen-6-one

Canonical SMILES:  COc1cc(-c2coc3cc4c(cc3c2=O)C=CC(C)(C)O4)ccc1OCC=C(C)C

Standard InChI:  InChI=1S/C26H26O5/c1-16(2)9-11-29-21-7-6-17(13-24(21)28-5)20-15-30-23-14-22-18(12-19(23)25(20)27)8-10-26(3,4)31-22/h6-10,12-15H,11H2,1-5H3

Standard InChI Key:  DFLROMXVXHQDBU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   -2.1825  -14.1791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1843  -12.5269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4693  -12.9359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4659  -13.7685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7470  -14.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0270  -13.7626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0305  -12.9300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7539  -12.5143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7448  -15.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6883  -14.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6867  -14.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4010  -15.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1151  -14.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1101  -14.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3951  -13.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8970  -13.7665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8974  -12.9395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6098  -12.5286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3265  -12.9402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3261  -13.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6090  -14.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8216  -13.7483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5384  -14.1561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8308  -15.4033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5433  -14.9881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2590  -15.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9715  -14.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6872  -15.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9682  -14.1578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5436  -12.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0433  -13.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  8  1  0
 14 15  2  0
 15 10  1  0
 16 17  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
 16  1  1  0
  5  9  2  0
 16 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
  1  4  2  0
 14 22  1  0
  6 10  1  0
 22 23  1  0
 13 24  1  0
 10 11  2  0
 24 25  1  0
  3  2  2  0
 25 26  1  0
 11 12  1  0
 26 27  2  0
  2 17  1  0
 27 28  1  0
 12 13  2  0
 27 29  1  0
  3  4  1  0
 19 30  1  0
 13 14  1  0
 19 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1773675

   PIERREIONE D

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: 418.49

Molecular Weight (Monoisotopic): 418.1780

AlogP: 6.00

#Rotatable Bonds: 5

Polar Surface Area: 57.90

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.28

CX LogD: 5.28

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.48

Np Likeness Score: 1.62

References

1. Gao S, Xu YM, Valeriote FA, Gunatilaka AA..  (2011)  Pierreiones A-D, solid tumor selective pyranoisoflavones and other cytotoxic constituents from Antheroporum pierrei.,  74  (4): [PMID:21452840] [10.1021/np100763p]

Source

Source(1):

• Scientific Literature