quercetin-3-O-[alpha-L-rhamnopyranosyl-(1->2)-[alpha-L-rhamnopyranosyl-(1->6)]-beta-D-galactopyranosyl]-7-O-beta-D-glucopyranoside

ID: ALA3746753

PubChem CID: 127039667

Max Phase: Preclinical

Molecular Formula: C39H50O25

Molecular Weight: 918.80

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](Oc3c(-c4ccc(O)c(O)c4)oc4cc(O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)cc(O)c4c3=O)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@@H](O)[C@H]2O)[C@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C39H50O25/c1-10-21(44)26(49)30(53)36(57-10)56-9-19-24(47)29(52)35(64-37-31(54)27(50)22(45)11(2)58-37)39(62-19)63-34-25(48)20-16(43)6-13(59-38-32(55)28(51)23(46)18(8-40)61-38)7-17(20)60-33(34)12-3-4-14(41)15(42)5-12/h3-7,10-11,18-19,21-24,26-32,35-47,49-55H,8-9H2,1-2H3/t10-,11-,18+,19+,21-,22-,23+,24-,26+,27+,28-,29-,30+,31+,32+,35+,36+,37-,38+,39-/m0/s1

Standard InChI Key:  XGAPXPDRYJCAOH-XWFFAPOZSA-N

Molfile:  

     RDKit          2D

 65 71  0  0  0  0  0  0  0  0999 V2000
    3.8917    1.5130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4785   -1.1715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8117    0.2121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7729    2.9118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1446    2.2596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2020    0.7811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4759    0.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7640    0.7971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7424    2.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4327    3.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4155    4.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    1.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6022    0.7450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6196   -0.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3293   -1.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0217   -0.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0043    0.7150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2678   -1.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2483   -3.0537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6657   -1.3428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3432   -2.7198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5377   -3.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5204   -5.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8107   -6.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1183   -5.3517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1357   -3.8518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8454   -3.0868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1818   -3.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4743   -5.9096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7968   -7.2866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1505   -5.9637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2165   -0.2188    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2803    2.9808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5433    5.9257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8899    7.5691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8986   10.2691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5647   11.6266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2546    8.1807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9202    9.8345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5512    7.4265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8526    8.1724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8574    9.6724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5608   10.4266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2594    9.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9605   10.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2402    5.1813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2300    3.6841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9102    2.9444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9307    5.9389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6292    5.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6189    3.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3174    2.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0261    3.7196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0364    5.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3379    5.9566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8984    1.7445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3092    1.7622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2582    5.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5636    5.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8563    5.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8438    7.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5385    8.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2458    7.4761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5285    9.4368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8779    8.1064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  1
  6  1  1  0
  7  2  1  1
  8  3  1  1
  9  4  1  6
 12 13  1  0
 12 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  1
 18 19  1  0
 14 20  1  1
 15 21  1  1
 13  1  1  6
 22 19  1  1
 22 23  1  0
 22 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  6
 23 29  1  6
 24 30  1  6
 25 31  1  1
  6 32  1  1
 12 33  1  1
 39 45  1  0
 44 38  1  0
 38 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 43 44  1  0
 44 45  1  1
 40 34  1  1
 41 35  1  6
 42 36  1  1
 43 37  1  6
 46 47  2  0
 47 48  1  0
 48 51  2  0
 50 49  2  0
 49 46  1  0
 50 51  1  0
 50 55  1  0
 51 52  1  0
 52 53  1  0
 53 54  2  0
 54 55  1  0
 48 56  1  0
 52 57  2  0
 58 59  2  0
 59 60  1  0
 60 61  2  0
 61 62  1  0
 62 63  2  0
 63 58  1  0
 54 58  1  0
 62 64  1  0
 61 65  1  0
 46 34  1  0
 53 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3746753

   ---

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: 918.80

Molecular Weight (Monoisotopic): 918.2641

AlogP: -5.36

#Rotatable Bonds: 11

Polar Surface Area: 407.50

Molecular Species: NEUTRAL

HBA: 25

HBD: 15

#RO5 Violations: 3

HBA (Lipinski): 25

HBD (Lipinski): 15

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 7.08

CX Basic pKa: ┄

CX LogP: -3.86

CX LogD: -4.36

Aromatic Rings: 3

Heavy Atoms: 64

QED Weighted: 0.08

Np Likeness Score: 1.72

References

1. Krasteva I, Bratkov V, Bucar F, Kunert O, Kollroser M, Kondeva-Burdina M, Ionkova I..  (2015)  Flavoalkaloids and Flavonoids from Astragalus monspessulanus.,  78  (11): [PMID:26558405] [10.1021/acs.jnatprod.5b00502]

Source

Source(1):

• Scientific Literature