(3beta,5alpha,25R)-3-[(beta-D-Cellobiosyl)chloro]spirostan-11-one

ID: ALA3138212

PubChem CID: 76333136

Max Phase: Preclinical

Molecular Formula: C39H60I2O12

Molecular Weight: 974.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1CC[C@@]2(OC1)OC1C[C@H]3[C@@H]4CC[C@H]5C[C@@H](OC6OC(CI)C(OC7OC(CI)C(O)C(O)C7O)C(O)C6O)CC[C@]5(C)[C@H]4C(=O)C[C@]3(C)C1[C@@H]2C

Standard InChI:  InChI=1S/C39H60I2O12/c1-17-7-10-39(48-16-17)18(2)27-24(53-39)12-22-21-6-5-19-11-20(8-9-37(19,3)28(21)23(42)13-38(22,27)4)49-35-33(47)31(45)34(26(15-41)51-35)52-36-32(46)30(44)29(43)25(14-40)50-36/h17-22,24-36,43-47H,5-16H2,1-4H3/t17?,18-,19-,20-,21-,22-,24?,25?,26?,27?,28+,29?,30?,31?,32?,33?,34?,35?,36?,37-,38-,39+/m0/s1

Standard InChI Key:  CRZLOTYQJUNAHZ-FGWJOSTPSA-N

Molfile:  

     RDKit          2D

 57 64  0  0  1  0  0  0  0  0999 V2000
   13.9845   -7.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9816   -8.4058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0253   -6.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4245  -10.9147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0014  -10.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1983  -10.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3007   -8.7789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6225   -8.3949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5490  -10.6731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3229  -10.5494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9298   -8.7740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7424   -7.3652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4457  -10.7789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6253   -7.5962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7606  -11.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9926   -7.8228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1989   -8.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0050   -9.8938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6535   -9.7817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2130  -10.4525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3064   -7.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3163  -10.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8769  -10.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2283  -10.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7379   -8.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2455   -6.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2488   -6.1606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9269   -9.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2978   -9.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8085  -10.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2634   -8.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6355   -6.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8571   -7.3907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2578   -9.9698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6169   -9.9746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5678   -9.5560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7671  -11.3379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9934  -11.4496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6573  -11.2349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8835  -11.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4273  -10.5760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9873   -6.8142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1073   -6.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5706   -8.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9265   -7.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6358   -9.3488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7662   -9.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4574   -6.6119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9898   -8.7218    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    6.8981   -8.9170    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   17.8892   -5.8624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6396   -6.1012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7110   -6.0918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9178  -10.4371    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.5931   -9.2217    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3299   -7.9433    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.0795   -9.2390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
 26  3  1  0
  4 20  1  0
  5 23  1  0
  6 30  1  0
  2  7  1  0
  8 14  1  0
  9  4  1  0
 10  6  1  0
  8 11  1  0
  1 12  1  0
 13 10  1  0
 14 21  1  0
 15  9  1  0
 16 17  1  0
 17 12  1  0
 18  4  1  0
 19  6  1  0
 20  5  1  0
  1 21  1  0
 22 24  1  0
 23 19  1  0
 24 18  1  0
  2 25  1  0
 26 12  1  0
  3 27  1  0
 11 28  1  0
  7 29  1  0
 36 30  1  1
 11 31  1  0
  3 32  1  0
 33 14  2  0
 28 34  1  0
 35 29  1  0
 36 44  1  0
 37 10  1  0
 38  9  1  0
 39 13  1  0
 40 15  1  0
 41 22  1  0
  1 42  1  1
 43 27  1  0
 44 31  1  0
 11 45  1  1
 46 23  1  0
 47 24  1  0
 48 32  1  0
 49 47  1  0
 50 46  1  0
 51 48  1  0
 26 52  1  6
 53 51  1  0
 28 54  1  6
 25 17  1  0
  7  8  1  0
  3 16  1  6
 28 35  1  0
 43 51  1  0
 36 34  1  0
  5 13  1  0
 22 15  1  0
  8 55  1  6
  7 56  1  1
  2 57  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3138212

   (1S,2S,6R,7S,9S,12S,13S,16S,18S)-16-[3,4-dihydroxy-6-(iodomethyl)-5-[3,4,5-trihydroxy-6-(iodomethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-11-one

Molecule Features

Natural Product: No

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: 974.71

Molecular Weight (Monoisotopic): 974.2174

AlogP: 3.51

#Rotatable Bonds: 6

Polar Surface Area: 173.60

Molecular Species: NEUTRAL

HBA: 12

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.95

CX Basic pKa: ┄

CX LogP: 4.50

CX LogD: 4.50

Aromatic Rings: ┄

Heavy Atoms: 53

QED Weighted: 0.15

Np Likeness Score: 2.40

References

1. DeNinno MP, McCarthy PA, Duplantier KC, Eller C, Etienne JB, Zawistoski MP, Bangerter FW, Chandler CE, Morehouse LA, Sugarman ED, Wilkins RW, Woody HA, Zaccaro LM..  (1997)  Steroidal glycoside cholesterol absorption inhibitors.,  40  (16): [PMID:9258361] [10.1021/jm9702600]

Source

Source(1):

• Scientific Literature