3'-methoxy-4'-(2R,3-dihydroxy-3-methylbutoxyl)-3'',3''-dimethylpyrano-(6,7)-isoflavone

ID: ALA1773673

Cas Number: 1292766-21-2

PubChem CID: 52951514

Max Phase: Preclinical

Molecular Formula: C26H28O7

Molecular Weight: 452.50

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Pierreione B | Pierreione B|1292766-21-2|CHEBI:68048|CHEMBL1773673|DTXSID801108928|7-[4-[(2R)-2,3-dihydroxy-3-methylbutoxy]-3-methoxyphenyl]-2,2-dimethylpyrano[3,2-g]chromen-6-one|HY-N3065|AKOS032961802|CS-0023142|Q27136544|3'-methoxy-4'-(2R,3-dihydroxy-3-methylbutoxyl)-3'',3''-dimethylpyrano-(6,7)-isoflavone|2H,6H-Benzo[1,2-b:5,4-b']dipyran-6-one, 7-[4-[(2R)-2,3-dihydroxy-3-methylbutoxy]-3-methoxyphenyl]-2,2-dimethyl-|7-(4-{[(2R)-2,3-dihydroxy-3-methylbutyl]oxy}-3-methoxyphenyl)-2,2-dimethyl-2HShow More⌵

Canonical SMILES:  COc1cc(-c2coc3cc4c(cc3c2=O)C=CC(C)(C)O4)ccc1OC[C@@H](O)C(C)(C)O

Standard InChI:  InChI=1S/C26H28O7/c1-25(2)9-8-16-10-17-21(12-20(16)33-25)31-13-18(24(17)28)15-6-7-19(22(11-15)30-5)32-14-23(27)26(3,4)29/h6-13,23,27,29H,14H2,1-5H3/t23-/m1/s1

Standard InChI Key:  RDXLWAJRBPKMPD-HSZRJFAPSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   -2.3708   -4.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3726   -2.5994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6573   -3.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6539   -3.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9348   -4.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2145   -3.8355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2180   -3.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9417   -2.5867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9326   -5.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5010   -4.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4994   -5.0712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2141   -5.4817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9283   -5.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -4.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2082   -3.8314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0855   -3.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0859   -3.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7986   -2.6011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5155   -3.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5151   -3.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7978   -4.2556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6352   -3.8212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3521   -4.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6444   -5.4768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3570   -5.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0731   -5.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7857   -5.0556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5018   -5.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7824   -4.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0765   -6.2958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4951   -4.6369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7326   -2.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2325   -3.4203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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  1  0
  2 17  1  0
 27 28  1  0
 12 13  2  0
 27 29  1  0
  3  4  1  0
 26 30  1  6
 13 14  1  0
 27 31  1  0
  3  8  1  0
 19 32  1  0
 14 15  2  0
 19 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1773673

   PIERREIONE B

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: 452.50

Molecular Weight (Monoisotopic): 452.1835

AlogP: 4.16

#Rotatable Bonds: 6

Polar Surface Area: 98.36

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.20

CX Basic pKa: ┄

CX LogP: 3.30

CX LogD: 3.30

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.58

Np Likeness Score: 1.70

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