Erythrodiol 3-O-[alpha-L-arabinopyranosyl-(1->3)]-beta-D-glucopyranosyl-(1->2)-beta-D-xylopyranoside

ID: ALA488528

PubChem CID: 21575015

Max Phase: Preclinical

Molecular Formula: C46H76O15

Molecular Weight: 869.10

Molecule Type: Small molecule

Names and Identifiers

Synonyms: nephelioside I | NEPHELIOSIDE I|CHEMBL488528

Canonical SMILES:  CC1(C)CC[C@]2(CO)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O[C@@H]6OC[C@@H](O)[C@H](O[C@@H]7OC[C@H](O)[C@H](O)[C@H]7O)[C@H]6O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1

Standard InChI:  InChI=1S/C46H76O15/c1-41(2)14-16-46(22-48)17-15-44(6)23(24(46)18-41)8-9-29-43(5)12-11-30(42(3,4)28(43)10-13-45(29,44)7)59-40-37(61-39-35(55)33(53)32(52)27(19-47)58-39)36(26(50)21-57-40)60-38-34(54)31(51)25(49)20-56-38/h8,24-40,47-55H,9-22H2,1-7H3/t24-,25-,26+,27+,28-,29+,30-,31-,32+,33-,34+,35+,36-,37+,38-,39-,40-,43-,44+,45+,46+/m0/s1

Standard InChI Key:  JBHHSGRRSOLJHT-NSAGBCCDSA-N

Molfile:  

     RDKit          2D

 64 71  0  0  0  0  0  0  0  0999 V2000
   -0.7165   -1.5247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4281   -1.1064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1448   -1.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1499   -2.3389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8563   -1.0951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5731   -1.5022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8513   -0.2697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5608    0.1450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1346    0.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4230   -0.2809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7053   -2.3591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2961   -3.0743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7097   -3.7873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5352   -3.7848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2979   -4.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7116   -5.2156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5275   -4.5051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9356   -5.2185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9411   -3.7922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5293   -3.0768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7654   -3.7936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1387   -1.5449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4272   -1.1266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7104   -1.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0011   -1.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0040   -0.2899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7055    0.1248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7206    0.1172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4323   -0.3011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8556   -0.3080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8556   -1.1322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5671   -1.5403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5671    0.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2784   -0.3080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2749   -1.1322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9830   -1.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6991   -1.1383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9900    0.1033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7027   -0.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7197    1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9954    0.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4323    0.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4188    0.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1265   -0.3410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8521    0.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1536    1.3179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8668    0.8858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5936    1.2851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6136    2.1182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9004    2.5504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1671    2.1495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2710    0.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6947    0.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4107   -0.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1471   -2.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9713   -2.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4806    3.2678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3048    3.2678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5753    0.4746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2901    0.8851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4833   -1.9232    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9829   -0.7201    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1476    0.4953    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1763   -4.5081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  1
 12 13  1  0
 30 33  1  0
 31 32  1  0
 32 35  1  0
 34 33  1  0
 34 35  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  1
 15 17  1  0
 34 38  1  0
 35 36  1  0
 36 37  1  0
 37 39  1  0
 38 39  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 12 20  1  0
 38 41  1  0
 39 43  1  0
 42 40  2  0
 40 41  1  0
 42 43  1  0
  2 10  1  0
 19 21  1  1
  2  1  1  1
 42 46  1  0
 43 44  1  0
 44 45  1  0
 45 47  1  0
 46 47  1  0
  2  3  1  0
  3  4  1  6
  3  5  1  0
  5  6  1  1
  5  7  1  0
  7  8  1  1
 46 51  1  0
 47 48  1  0
 48 49  1  0
 49 50  1  0
 50 51  1  0
 23 22  1  1
 34 52  1  1
 23 24  1  0
 39 53  1  1
 24 11  1  6
 43 54  1  6
 24 25  1  0
 32 55  1  0
 25  1  1  1
 32 56  1  0
 31 22  1  1
 25 26  1  0
 50 57  1  0
 26 27  1  6
 50 58  1  0
 26 28  1  0
 47 59  1  1
 28 29  1  0
 59 60  1  0
 23 29  1  0
 35 61  1  6
 30 31  1  0
 38 62  1  6
  7  9  1  0
 46 63  1  1
  9 10  1  0
 21 64  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA488528

   NEPHELIOSIDE I

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: 869.10

Molecular Weight (Monoisotopic): 868.5184

AlogP: 1.89

#Rotatable Bonds: 8

Polar Surface Area: 237.45

Molecular Species: NEUTRAL

HBA: 15

HBD: 9

#RO5 Violations: 3

HBA (Lipinski): 15

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.91

CX Basic pKa: ┄

CX LogP: 2.07

CX LogD: 2.07

Aromatic Rings: ┄

Heavy Atoms: 61

QED Weighted: 0.13

Np Likeness Score: 2.55

References

1. Ito A, Chai HB, Kardono LB, Setowati FM, Afriastini JJ, Riswan S, Farnsworth NR, Cordell GA, Pezzuto JM, Swanson SM, Kinghorn AD..  (2004)  Saponins from the bark of Nephelium maingayi.,  67  (2): [PMID:14987059] [10.1021/np030389e]

Source

Source(1):

• Scientific Literature