Glabrisoflavone

ID: ALA1086439

PubChem CID: 5378945

Max Phase: Preclinical

Molecular Formula: C20H18O6

Molecular Weight: 354.36

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Glabrisoflavone | Hydroxywighteone|5,7,4'-Trihydroxy-6-(3-hydroxymethyl-2-butenyl)isoflavone|Glabrisoflavone|CHEMBL1086439|AROTXIUFXQZGLT-BIIKFXOESA-N|LMPK12050195|5,7-dihydroxy-6-[(E)-4-hydroxy-3-methylbut-2-enyl]-3-(4-hydroxyphenyl)chromen-4-one|5,7,4'-Trihydroxy-6-[3-(hydroxymethyl)but-2-enyl]isoflavone|(e)-5,7,4'-trihydroxy-6-(3-hydroxymethyl-2-butenyl)isoflavone|5,7-Dihydroxy-6-[4-hydroxy-3-methyl-2-butenyl]-3-(4-hydroxyphenyl)-4H-chromen-4-one

Canonical SMILES:  C/C(=C\Cc1c(O)cc2occ(-c3ccc(O)cc3)c(=O)c2c1O)CO

Standard InChI:  InChI=1S/C20H18O6/c1-11(9-21)2-7-14-16(23)8-17-18(19(14)24)20(25)15(10-26-17)12-3-5-13(22)6-4-12/h2-6,8,10,21-24H,7,9H2,1H3/b11-2+

Standard InChI Key:  AROTXIUFXQZGLT-BIIKFXOESA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    4.8996   -6.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8983   -6.8308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6113   -7.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6093   -5.5905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3274   -5.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3264   -6.8328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0439   -7.2481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7668   -6.8344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7677   -6.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0457   -5.5810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1834   -7.2422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6054   -4.7656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0455   -4.7561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4782   -5.5915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1920   -6.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9069   -5.5969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9089   -4.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1904   -4.3573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4787   -4.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6238   -4.3592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1849   -5.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4709   -6.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7561   -5.5926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0420   -6.0057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7554   -4.7677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3273   -5.5938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
 10 13  2  0
  3  6  2  0
  1  2  2  0
 14 15  2  0
  5  4  2  0
 15 16  1  0
  4  1  1  0
 16 17  2  0
  5 10  1  0
 17 18  1  0
  6  7  1  0
 18 19  2  0
 19 14  1  0
  9 14  1  0
  7  8  1  0
 17 20  1  0
  8  9  2  0
  1 21  1  0
  9 10  1  0
 21 22  1  0
  5  6  1  0
 22 23  2  0
  2 11  1  0
 23 24  1  0
 23 25  1  0
  4 12  1  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1086439

   GLABRISOFLAVONE

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: 354.36

Molecular Weight (Monoisotopic): 354.1103

AlogP: 3.06

#Rotatable Bonds: 4

Polar Surface Area: 111.13

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.36

CX Basic pKa: ┄

CX LogP: 3.52

CX LogD: 2.38

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.54

Np Likeness Score: 2.01

References

1. Allen JG, Fotsch C, Babij P..  (2010)  Emerging targets in osteoporosis disease modification.,  53  (11): [PMID:20218623] [10.1021/jm9018756]

Source

Source(1):

• Scientific Literature