(2R,3S,4R,5S,6S)-6-(5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-3-yloxy)-4,5-dihydroxy-2-methyltetrahydro-2H-pyran-3-yl 3,4,5-trihydroxybenzoate

ID: ALA445807

PubChem CID: 44559341

Max Phase: Preclinical

Molecular Formula: C28H24O16

Molecular Weight: 616.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1O[C@@H](Oc2c(-c3cc(O)c(O)c(O)c3)oc3cc(O)cc(O)c3c2=O)[C@@H](O)[C@@H](O)[C@@H]1OC(=O)c1cc(O)c(O)c(O)c1

Standard InChI:  InChI=1S/C28H24O16/c1-8-24(43-27(40)10-4-15(33)20(36)16(34)5-10)22(38)23(39)28(41-8)44-26-21(37)18-12(30)6-11(29)7-17(18)42-25(26)9-2-13(31)19(35)14(32)3-9/h2-8,22-24,28-36,38-39H,1H3/t8-,22-,23+,24-,28+/m1/s1

Standard InChI Key:  SOXQRBCUPOQXQV-RIZUBJKGSA-N

Molfile:  

     RDKit          2D

 44 48  0  0  0  0  0  0  0  0999 V2000
   14.0705  -25.5271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0716  -24.7015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3584  -24.2896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6434  -24.7021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6463  -25.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3602  -25.9390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9349  -25.9451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3628  -26.7622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7836  -25.9385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3585  -23.4663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0715  -23.0548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6456  -23.0546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6015  -19.7624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6118  -20.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3301  -20.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0382  -20.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3403  -21.8133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0586  -22.2154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6342  -22.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9159  -21.8298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9037  -21.0090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2078  -22.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9352  -18.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9049  -19.3238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1749  -19.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4773  -19.2702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7451  -19.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0433  -19.2201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0736  -18.3921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8035  -18.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5054  -18.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2375  -18.0546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6674  -18.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6977  -17.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4277  -16.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1295  -17.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1014  -18.1548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3692  -18.5459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8032  -18.5960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8617  -16.9434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4580  -16.0653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1445  -20.5353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3717  -17.9509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7169  -20.4816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 20 22  1  1
 14 21  1  0
 10 11  2  0
  5  6  2  0
 10 12  1  0
  6  1  1  0
  1  2  2  0
  5  7  1  0
  3  4  2  0
  6  8  1  0
  1  9  1  0
  4  5  1  0
  3 10  1  0
  2  3  1  0
 14 13  1  1
 14 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  1
 17 19  1  0
 19 12  1  6
 19 20  1  0
 20 21  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 26 31  2  0
 31 32  1  0
 23 32  1  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 33 38  2  0
 37 39  1  0
 36 40  1  0
 35 41  1  0
 23 33  1  0
 25 42  2  0
 29 43  1  0
 27 44  1  0
 24 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA445807

   [(2R,3S,4R,5S,6S)-6-[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy-4,5-dihydroxy-2-methyloxan-3-yl] 3,4,5-trihydroxybenzoate

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: 616.48

Molecular Weight (Monoisotopic): 616.1064

AlogP: 1.18

#Rotatable Bonds: 5

Polar Surface Area: 277.27

Molecular Species: ACID

HBA: 16

HBD: 10

#RO5 Violations: 3

HBA (Lipinski): 16

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 6.36

CX Basic pKa: ┄

CX LogP: 2.18

CX LogD: 0.90

Aromatic Rings: 4

Heavy Atoms: 44

QED Weighted: 0.11

Np Likeness Score: 1.82

References

1. Nicollier G, Thompson AC.  (1983)  Flavonoids of Desmanthus illinoensis,  46  (1): [10.1021/np50025a011]

Source

Source(1):

• Scientific Literature