6-methoxy-7-(3-methylbuta-1,3-dien-1-yl)-9H-xanthene-1,4,8-triol

ID: ALA5287562

Max Phase: Preclinical

Molecular Formula: C19H18O5

Molecular Weight: 326.35

Names and Identifiers

Canonical SMILES:  C=C(C)/C=C/c1c(OC)cc2c(c1O)Cc1c(O)ccc(O)c1O2

Standard InChI:  InChI=1S/C19H18O5/c1-10(2)4-5-11-16(23-3)9-17-13(18(11)22)8-12-14(20)6-7-15(21)19(12)24-17/h4-7,9,20-22H,1,8H2,2-3H3/b5-4+

Standard InChI Key:  YHXSFXRNDCCSJZ-SNAWJCMRSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   -2.8567    1.6504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8567    0.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5712    0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5712   -0.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8549   -0.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1449   -0.4113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4304   -0.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7159   -0.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0016   -0.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0016   -1.6504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7131   -0.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7131    0.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034    0.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7159    0.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4304    0.8261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1449    0.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4277    0.8245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4277    1.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4277   -0.8214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1421   -0.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8567   -0.8214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5712   -0.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8567   -1.6464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8549   -1.6481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 14 13  1  0
  8 14  2  0
 14 15  1  0
 16 15  1  0
  6 16  2  0
 16  2  1  0
 12 17  1  0
 17 18  1  0
 11 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  5 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5287562

   ---

Molecule Features

Natural Product: No

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: 326.35

Molecular Weight (Monoisotopic): 326.1154

AlogP: 4.10

#Rotatable Bonds: 3

Polar Surface Area: 79.15

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.65

CX Basic pKa: ┄

CX LogP: 4.03

CX LogD: 4.01

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.50

Np Likeness Score: 1.65

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