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

ID: ALA1159510

PubChem CID: 46905167

Max Phase: Preclinical

Molecular Formula: C28H32O13

Molecular Weight: 576.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C=C(c2ccc(O)cc2)Oc2cc(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)cc(O)c21

Standard InChI:  InChI=1S/C28H32O13/c1-11-7-17(13-3-5-14(30)6-4-13)39-18-9-15(8-16(31)20(11)18)38-28-26(24(35)22(33)19(10-29)40-28)41-27-25(36)23(34)21(32)12(2)37-27/h3-9,12,19,21-36H,1,10H2,2H3/t12-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1

Standard InChI Key:  IWDNCEBIMSBKKV-RNJSHNQESA-N

Molfile:  

     RDKit          2D

 41 45  0  0  0  0  0  0  0  0999 V2000
   -6.5043    2.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2187    2.9170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9332    2.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9332    1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2188    1.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5043    1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6477    2.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3622    2.5045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6477    1.2670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2188    0.4420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7898    1.2670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7898    0.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0753    0.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5043    0.0295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5043   -0.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7898   -1.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0753   -0.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2188   -1.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7898   -2.0330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3609   -1.2080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3609    0.4420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7898    2.9170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9648    2.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2503    3.3295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9648    2.0920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2503    1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5358    2.0920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5358    2.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8213    3.3295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1068    2.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1068    2.0920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8213    1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3924    3.3295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6779    2.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0366    3.3295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0366    4.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6779    4.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3924    4.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7510    4.5670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8213    0.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2503    0.8545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  6  1  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  3  7  1  1
  7  8  1  0
  4  9  1  6
  5 10  1  1
  6 11  1  6
 12 11  1  1
 13 12  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
 15 18  1  6
 16 19  1  1
 17 20  1  6
 13 21  1  6
  1 22  1  1
 22 23  1  0
 24 23  2  0
 23 25  1  0
 24 28  1  0
 25 26  2  0
 26 27  1  0
 32 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 30 33  1  0
 33 34  1  0
 33 38  2  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 36 39  1  0
 32 40  2  0
 26 41  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1159510

   (2S,3R,4R,5R,6S)-2-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-[5-hydroxy-2-(4-hydroxyphenyl)-4-methylidenechromen-7-yl]oxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-methyloxane-3,4,5-triol

Molecule Features

Natural Product: No

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: 576.55

Molecular Weight (Monoisotopic): 576.1843

AlogP: -0.42

#Rotatable Bonds: 6

Polar Surface Area: 207.99

Molecular Species: NEUTRAL

HBA: 13

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 13

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 8.83

CX Basic pKa: ┄

CX LogP: -0.07

CX LogD: -0.09

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.22

Np Likeness Score: 2.06

References

1. Tang R, Chen K, Cosentino M, Lee K.  (1994)  Apigenin-7-O--D-glucopyranoside, an anti-HIV principle from Kummerowia striata,  4  (3): [10.1016/0960-894X(94)80015-4]

Source

Source(1):

• Scientific Literature