8,5'-dihydroxy-7,3',4'-trimethoxyflavone

ID: ALA464701

Cas Number: 133343-00-7

PubChem CID: 44257590

Max Phase: Preclinical

Molecular Formula: C18H16O7

Molecular Weight: 344.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(-c2cc(=O)c3ccc(OC)c(O)c3o2)cc(O)c1OC

Standard InChI:  InChI=1S/C18H16O7/c1-22-13-5-4-10-11(19)8-14(25-17(10)16(13)21)9-6-12(20)18(24-3)15(7-9)23-2/h4-8,20-21H,1-3H3

Standard InChI Key:  RHXKHTYRDAJUEZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    8.4809  -18.9459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4798  -19.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1938  -20.1848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1920  -18.5336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9067  -18.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9101  -19.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6285  -20.1853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3481  -19.7686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3446  -18.9364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6216  -18.5209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0560  -18.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7712  -18.9340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4831  -18.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4810  -17.6954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7610  -17.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0521  -17.7017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7672  -18.5340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0536  -18.9463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7556  -16.4617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4666  -16.0449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1929  -17.2803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1893  -16.4562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1980  -18.9307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6307  -21.0094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1895  -17.7095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
 12 13  1  0
  3  6  2  0
 13 14  2  0
  1  2  2  0
 14 15  1  0
  5  4  2  0
 15 16  2  0
 16 11  1  0
  9 11  1  0
  4  1  1  0
  1 17  1  0
  5 10  1  0
 17 18  1  0
  6  7  1  0
 15 19  1  0
  7  8  1  0
 19 20  1  0
  8  9  2  0
 14 21  1  0
  9 10  1  0
 21 22  1  0
  5  6  1  0
 13 23  1  0
  7 24  2  0
 11 12  2  0
  4 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA464701

   8,3'-Dihydroxy-7,4',5'-trimethoxyflavone

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: 344.32

Molecular Weight (Monoisotopic): 344.0896

AlogP: 2.90

#Rotatable Bonds: 4

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: 8.49

CX Basic pKa: ┄

CX LogP: 1.89

CX LogD: 1.85

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.75

Np Likeness Score: 1.21

References

1. Kaneda N, Pezzuto JM, Soejarto DD, Kinghorn AD, Farnsworth NR, Santisuk T, Tuchinda P, Udchachon J, Reutrakul V..  (1991)  Plant anticancer agents, XLVIII. New cytotoxic flavonoids from Muntingia calabura roots.,  54  (1): [PMID:2045815] [10.1021/np50073a019]

Source

Source(1):

• Scientific Literature