sodium (16S,20S,24E)-16,20-dihydroxy-19-norstigmasta-1,3,5(10),24(28)-tetraen-3a-yl sulfate

ID: ALA1080082

PubChem CID: 44254698

Max Phase: Preclinical

Molecular Formula: C28H41NaO6S

Molecular Weight: 506.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C=C(\CC[C@](C)(O)[C@H]1[C@@H](O)C[C@H]2[C@@H]3CCc4cc(OS(=O)(=O)[O-])ccc4[C@H]3CC[C@@]21C)C(C)C.[Na+]

Standard InChI:  InChI=1S/C28H42O6S.Na/c1-6-18(17(2)3)11-14-28(5,30)26-25(29)16-24-23-9-7-19-15-20(34-35(31,32)33)8-10-21(19)22(23)12-13-27(24,26)4;/h6,8,10,15,17,22-26,29-30H,7,9,11-14,16H2,1-5H3,(H,31,32,33);/q;+1/p-1/b18-6+;/t22-,23-,24+,25+,26+,27+,28+;/m1./s1

Standard InChI Key:  GTNJPNDGDVGGKT-WUOFOQQUSA-M

Molfile:  

     RDKit          2D

 40 42  0  0  0  0  0  0  0  0999 V2000
   -3.8376   -3.4259    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   -2.3423   -0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3434   -1.7610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6301   -2.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6319   -0.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9180   -0.9318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9146   -1.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1970   -2.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5219   -1.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2039   -0.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5180   -0.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5192    0.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2064    0.3211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2410    0.3180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2329   -0.5176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0250   -0.7836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5228   -0.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0382    0.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0566   -2.1721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7693   -1.7599    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4862   -1.3471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3578   -1.0470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1772   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2120   -1.3304    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5114   -0.1040    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2266   -1.3388    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3004    1.3487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1072    1.5119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7555    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5113    2.1496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6521    0.8947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4589    1.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0038    0.4408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7210    1.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1762    2.4555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7416   -0.3396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8106    0.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3460   -0.1205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8606    0.5696    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2348    1.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3 19  1  0
  8  9  1  0
 19 20  1  0
  9 11  1  0
 20 21  1  0
 10 11  1  0
 20 22  2  0
 20 23  2  0
  6  5  2  0
 10 24  1  6
  5  2  1  0
 11 25  1  1
  6  7  1  0
 15 26  1  6
 10 13  1  0
 18 27  1  0
 11 15  1  0
 27 28  1  0
 14 12  1  0
 27 29  1  0
 12 13  1  0
 27 30  1  1
 14 15  1  0
 28 31  1  0
  2  3  2  0
 31 32  1  0
 32 33  1  0
  3  4  1  0
 32 34  2  0
  4  7  2  0
 34 35  1  0
  6 10  1  0
 33 36  1  0
 15 16  1  0
 33 37  1  0
 16 17  1  0
 17 38  1  1
 17 18  1  0
 18 39  1  6
 18 14  1  0
 14 40  1  1
  7  8  1  0
M  CHG  2   1   1  21  -1
M  END

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: 506.71

Molecular Weight (Monoisotopic): 506.2702

AlogP: 5.44

#Rotatable Bonds: 7

Polar Surface Area: 104.06

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -1.75

CX Basic pKa: ┄

CX LogP: 3.59

CX LogD: 2.87

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.34

Np Likeness Score: 2.25

References

1. Digirolamo JA, Li XC, Jacob MR, Clark AM, Ferreira D..  (2009)  Reversal of fluconazole resistance by sulfated sterols from the marine sponge Topsentia sp.,  72  (8): [PMID:19653640] [10.1021/np900177m]

Source

Source(1):

• Scientific Literature