kaempferol 3-O-alpha-L-rhamnopyranosyl(1'''->6'')-beta-D-glucopyranoside

ID: ALA255020

PubChem CID: 44445551

Max Phase: Preclinical

Molecular Formula: C27H30O15

Molecular Weight: 594.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1O[C@@H](OC[C@H]2O[C@@H](Oc3c(-c4ccc(O)cc4)oc4cc(O)cc(O)c4c3=O)[C@H](O)[C@@H](O)[C@@H]2O)[C@@H](O)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C27H30O15/c1-9-17(31)20(34)22(36)26(39-9)38-8-15-18(32)21(35)23(37)27(41-15)42-25-19(33)16-13(30)6-12(29)7-14(16)40-24(25)10-2-4-11(28)5-3-10/h2-7,9,15,17-18,20-23,26-32,34-37H,8H2,1H3/t9-,15-,17-,18-,20+,21+,22+,23-,26-,27+/m1/s1

Standard InChI Key:  RTATXGUCZHCSNG-WJJLTQTOSA-N

Molfile:  

     RDKit          2D

 42 46  0  0  1  0  0  0  0  0999 V2000
   14.4762   -6.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4762   -5.8756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1795   -7.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7636   -7.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1795   -5.4631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7636   -5.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8996   -6.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1795   -7.9346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0533   -6.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7636   -7.9346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8996   -5.8756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0533   -5.8756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6184   -7.1166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6095   -5.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3248   -5.4535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5927   -4.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3253   -5.8756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3059   -4.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0322   -5.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0322   -4.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7711   -4.2258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6176   -7.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9065   -8.3530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9037   -9.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6159   -9.5915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3326   -9.1810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3371   -8.3534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1873   -9.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4748   -9.1675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0453   -9.5967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6119  -10.4165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0519   -7.9414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7583   -9.5766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0498   -9.1554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3355   -9.5609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3273  -10.3863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0396  -10.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7601  -10.3972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4731  -10.8122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0328  -11.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6246   -9.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6093  -10.7926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7 11  2  0
  9 12  1  0
 19 20  1  0
 22 13  1  1
 22 23  1  0
  1  2  2  0
  1  3  1  0
  1  4  1  0
  2  5  1  0
  2  6  1  0
 22 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
  3  7  1  0
 24 28  1  1
  3  8  2  0
 28 29  1  0
  4  9  2  0
 26 30  1  1
  4 10  1  0
 25 31  1  6
  5 11  1  0
 27 32  1  6
  6 12  2  0
 33 29  1  1
 33 34  1  0
  7 13  1  0
 11 14  1  0
 12 15  1  0
 14 16  2  0
 14 17  1  0
 33 38  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 16 18  1  0
 38 39  1  1
 17 19  2  0
 37 40  1  1
 18 20  2  0
 35 41  1  1
 20 21  1  0
 36 42  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA255020

   5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]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: 594.52

Molecular Weight (Monoisotopic): 594.1585

AlogP: -1.39

#Rotatable Bonds: 6

Polar Surface Area: 249.20

Molecular Species: ACID

HBA: 15

HBD: 9

#RO5 Violations: 3

HBA (Lipinski): 15

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 6.37

CX Basic pKa: ┄

CX LogP: -0.57

CX LogD: -1.72

Aromatic Rings: 3

Heavy Atoms: 42

QED Weighted: 0.16

Np Likeness Score: 1.94

References

1. Yoon KD, Jeong DG, Hwang YH, Ryu JM, Kim J..  (2007)  Inhibitors of osteoclast differentiation from Cephalotaxus koreana.,  70  (12): [PMID:17994703] [10.1021/np070327e]

Source

Source(1):

• Scientific Literature