5bea,14beta-dihydroxy-19-oxo-3beta-[(alpha-L-rhamnopyranosyl)oxy)]bufa-20,22-dienolide

ID: ALA443199

Cas Number: 20300-44-1

PubChem CID: 44584382

Max Phase: Preclinical

Molecular Formula: C30H42O10

Molecular Weight: 562.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H]1O[C@@H](O[C@H]2CC[C@]3(C=O)[C@H]4CC[C@]5(C)[C@@H](c6ccc(=O)oc6)CC[C@]5(O)[C@@H]4CC[C@]3(O)C2)[C@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C30H42O10/c1-16-23(33)24(34)25(35)26(39-16)40-18-5-10-28(15-31)20-6-9-27(2)19(17-3-4-22(32)38-14-17)8-12-30(27,37)21(20)7-11-29(28,36)13-18/h3-4,14-16,18-21,23-26,33-37H,5-13H2,1-2H3/t16-,18-,19+,20-,21+,23-,24+,25+,26-,27+,28-,29-,30-/m0/s1

Standard InChI Key:  HNNFRQFXBWSJBX-MTUTWWBMSA-N

Molfile:  

     RDKit          2D

 43 48  0  0  0  0  0  0  0  0999 V2000
    4.0732   -8.1585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0784   -8.9808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7919   -9.3891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7924  -10.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0779  -10.6256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3690  -10.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3638   -9.3997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6545  -10.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7825   -6.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7825   -7.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4945   -8.1616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4945   -6.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2116   -6.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2095   -7.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9211   -8.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6384   -7.7516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9285   -6.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6412   -6.9270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6544   -5.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3671   -5.6944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3646   -6.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1427   -6.7817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6320   -6.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1619   -5.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2059   -6.0955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9142   -5.6765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4904   -5.6912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9229   -7.3298    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6328   -6.1036    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3601   -4.8692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4231   -4.6684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2265   -4.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4895   -3.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9467   -3.1160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1398   -3.2721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8714   -4.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2159   -2.3351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4730   -8.4113    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5064   -8.9779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5091  -10.6227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0877  -11.4526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2059   -8.5651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3544   -7.3434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  6
  2  7  1  0
  9 10  1  0
  9 12  1  0
 10 11  1  0
 11 14  1  0
 13 12  1  0
 13 14  1  0
 13 17  1  0
 14 15  1  0
 15 16  1  0
 16 18  1  0
 17 18  1  0
 17 26  1  0
 18 21  1  0
 20 19  1  0
 19 26  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 20  1  0
 10  1  1  1
 13 25  1  1
 25 27  2  0
 17 28  1  6
 18 29  1  1
 20 30  1  1
 24 31  1  1
 31 32  1  0
 31 36  2  0
 32 33  2  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 34 37  2  0
  2 38  1  6
  2  1  1  0
  2  3  1  0
  3  4  1  0
  3 39  1  6
  5 41  1  1
 14 42  1  1
  4 40  1  6
 21 43  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA443199

   Desglucohellebrin

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: 562.66

Molecular Weight (Monoisotopic): 562.2778

AlogP: 1.39

#Rotatable Bonds: 4

Polar Surface Area: 166.89

Molecular Species: NEUTRAL

HBA: 10

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.22

CX Basic pKa: 0.30

CX LogP: 0.35

CX LogD: 0.35

Aromatic Rings: 1

Heavy Atoms: 40

QED Weighted: 0.27

Np Likeness Score: 2.87

References

1. Watanabe K, Mimaki Y, Sakagami H, Sashida Y..  (2003)  Bufadienolide and spirostanol glycosides from the rhizomes of helleborusorientalis.,  66  (2): [PMID:12608856] [10.1021/np0203638]

Source

Source(1):

• Scientific Literature