2-(3,4-Dihydroxy-phenyl)-5-hydroxy-7-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-chromen-4-one

ID: ALA1159535

PubChem CID: 13093776

Max Phase: Preclinical

Molecular Formula: C21H20O11

Molecular Weight: 448.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1cc(-c2ccc(O)c(O)c2)oc2cc(O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)cc(O)c12

Standard InChI:  InChI=1S/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)30-9-4-12(25)17-13(26)6-14(31-15(17)5-9)8-1-2-10(23)11(24)3-8/h1-6,16,18-25,27-29H,7H2/t16-,18-,19+,20-,21+/m1/s1

Standard InChI Key:  PEFNSGRTCBGNAN-RQXATKFSSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    2.8875    6.6884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    7.1009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    7.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    8.3384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730    7.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1730    7.1009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164    8.3384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0309    7.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0309    7.1009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164    6.6884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454    8.3384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4599    7.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1744    8.3384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1743    9.1634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4598    9.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454    9.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3165    5.8634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    5.8634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4586    8.3384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7441    7.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0296    8.3384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6849    7.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6849    7.1009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0296    6.6884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7441    7.1009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3993    8.3384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1138    7.9259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3993    6.6884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0296    5.8634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4586    6.6884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4598   10.4010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888    9.5759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
 10  2  1  0
  2  3  1  0
  3  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 16  2  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 10 17  2  0
  1 18  1  0
  5 19  1  0
 20 19  1  6
 20 21  1  0
 25 20  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 22 26  1  1
 26 27  1  0
 23 28  1  6
 24 29  1  1
 25 30  1  6
 15 31  1  0
 14 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1159535

   2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

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: 448.38

Molecular Weight (Monoisotopic): 448.1006

AlogP: -0.24

#Rotatable Bonds: 4

Polar Surface Area: 190.28

Molecular Species: NEUTRAL

HBA: 11

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.30

CX Basic pKa: ┄

CX LogP: 0.14

CX LogD: -0.23

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.26

Np Likeness Score: 1.97

References

1. Kubo I, Kinst-Hori I, Ishiguro K, Chaudhuri SK, Sanchez Y, Ogura T.  (1994)  Tyrosinase inhibitory flavonoids fromheterotheca inuloides and their structural functions,  4  (12): [10.1016/S0960-894X(01)80510-2]

2. PubChem BioAssay data set, 

3. PubChem BioAssay data set, 

4. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays