5,7,10-trihydroxy-1,1,2-trimethyl-1,2-dihydro-6H-furo[2,3-c]xanthen-6-one

ID: ALA5279710

Max Phase: Preclinical

Molecular Formula: C18H16O6

Molecular Weight: 328.32

Names and Identifiers

Canonical SMILES:  CC1Oc2cc(O)c3c(=O)c4c(O)ccc(O)c4oc3c2C1(C)C

Standard InChI:  InChI=1S/C18H16O6/c1-7-18(2,3)14-11(23-7)6-10(21)13-15(22)12-8(19)4-5-9(20)16(12)24-17(13)14/h4-7,19-21H,1-3H3

Standard InChI Key:  KIUHCQDWGHJIMP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    1.0888   -2.0481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0888   -1.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3712   -0.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3712    0.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0837    0.4265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8002    0.0141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8002   -0.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4050    0.5711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0712    1.3319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2683    1.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0544    2.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717    1.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4837    2.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3431    0.4282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0576    0.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0576   -0.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3431   -1.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3431   -2.0466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7675   -1.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4837   -0.8128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4837    0.0153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7693    0.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7693    1.2525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7675   -2.0458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  3  4  2  0
  4  5  1  0
  6  5  2  0
  7  6  1  0
  2  7  2  0
  6  8  1  0
  8  9  1  0
 10  9  1  0
  5 10  1  0
 10 11  1  0
 10 12  1  0
  9 13  1  0
  4 14  1  0
 15 14  1  0
 16 15  2  0
 16 17  1  0
 17  3  1  0
 17 18  2  0
 19 16  1  0
 20 19  2  0
 21 20  1  0
 22 21  2  0
 15 22  1  0
 22 23  1  0
 19 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5279710

   ---

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 328.32

Molecular Weight (Monoisotopic): 328.0947

AlogP: 3.12

#Rotatable Bonds: ┄

Polar Surface Area: 100.13

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.11

CX Basic pKa: ┄

CX LogP: 4.39

CX LogD: 4.31

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.43

Np Likeness Score: 2.45

References

1. Santos CMM, Freitas M, Fernandes E..  (2018)  A comprehensive review on xanthone derivatives as α-glucosidase inhibitors.,  157  [PMID:30282319] [10.1016/j.ejmech.2018.07.073]

Source

Source(1):

• Scientific Literature