6,6',6'',7,7',7''-hexahydroxy-2H,2'H,2''H-[5,5':8',8''-terbenzo[b]pyran]-2,2',2''-trione

ID: ALA5287703

Max Phase: Preclinical

Molecular Formula: C27H14O12

Molecular Weight: 530.40

Names and Identifiers

Canonical SMILES:  O=c1ccc2c(-c3c(O)c(O)c(-c4c(O)c(O)cc5ccc(=O)oc45)c4oc(=O)ccc34)c(O)c(O)cc2o1

Standard InChI:  InChI=1S/C27H14O12/c28-12-7-9-1-4-16(31)38-26(9)20(23(12)34)21-25(36)24(35)19(11-3-6-17(32)39-27(11)21)18-10-2-5-15(30)37-14(10)8-13(29)22(18)33/h1-8,28-29,33-36H

Standard InChI Key:  OYHPLKRRSXCLPL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 39 44  0  0  0  0  0  0  0  0999 V2000
   -1.4281    2.1351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7135    1.7228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0017    2.1347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0017    2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7117    3.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4281    2.9636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7129    1.7221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4276    2.1347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4276    2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7129    3.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1422    1.7221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1427    1.7225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1427    3.3762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1421   -1.7221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1421   -3.3758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1427   -3.3762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7135   -1.7258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4281   -2.1384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7135   -3.3762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4281   -2.9636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4276   -2.1347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7112   -1.7266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0010   -2.1384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0010   -2.9636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4276   -2.9632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7130   -3.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1421   -0.9059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1421    0.7476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1427    0.7480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7135   -0.9023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4281   -0.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7135    0.7480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4281    0.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4276   -0.4933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7112   -0.9014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0010   -0.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0010    0.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4276    0.3351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7130    0.7473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  3  7  1  0
  8  7  1  0
  9  8  1  0
 10  9  2  0
  4 10  1  0
  8 11  2  0
  1 12  1  0
  6 13  1  0
 17 18  2  0
 20 19  1  0
 18 20  1  0
 20 16  2  0
 21 14  1  0
 21 22  2  0
 22 23  1  0
 23 17  1  0
 23 24  2  0
 24 19  1  0
 25 21  1  0
 25 15  1  0
 26 25  2  0
 24 26  1  0
 30 31  2  0
 33 32  1  0
 31 33  1  0
 33 29  2  0
 34 27  1  0
 34 35  2  0
 35 22  1  0
 35 36  1  0
 36 30  1  0
 36 37  2  0
 37 32  1  0
 38 34  1  0
 38 28  1  0
 39 38  2  0
 37 39  1  0
 39  2  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5287703

   ---

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: 530.40

Molecular Weight (Monoisotopic): 530.0485

AlogP: 3.57

#Rotatable Bonds: 2

Polar Surface Area: 212.01

Molecular Species: ACID

HBA: 12

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 6.25

CX Basic pKa: ┄

CX LogP: 2.88

CX LogD: 1.54

Aromatic Rings: 6

Heavy Atoms: 39

QED Weighted: 0.14

Np Likeness Score: 0.80

References

1. Han Jeong G, Cho JH, Park KI, Kim K, Hoon Kim T..  (2023)  Enzymatic transformation of esculetin as a potent class of α-glucosidase inhibitors.,  88  [PMID:37088219] [10.1016/j.bmcl.2023.129302]

Source

Source(1):

• Scientific Literature