17-epiestriol-3-glucuronide

ID: ALA3526999

PubChem CID: 118753213

Max Phase: Preclinical

Molecular Formula: C24H32O9

Molecular Weight: 464.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12CC[C@@H]3c4ccc(O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]5O)cc4CC[C@H]3[C@@H]1C[C@@H](O)[C@H]2O

Standard InChI:  InChI=1S/C24H32O9/c1-24-7-6-13-12-5-3-11(32-23-19(28)17(26)18(27)20(33-23)22(30)31)8-10(12)2-4-14(13)15(24)9-16(25)21(24)29/h3,5,8,13-21,23,25-29H,2,4,6-7,9H2,1H3,(H,30,31)/t13-,14-,15+,16-,17+,18+,19-,20+,21-,23-,24+/m1/s1

Standard InChI Key:  UZKIAJMSMKLBQE-PHEYUCJMSA-N

Molfile:  

     RDKit          2D

 36 40  0  0  0  0  0  0  0  0999 V2000
   11.5969  -13.8547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0328  -14.6769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0383  -16.3321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6101  -17.1616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8845  -15.0989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3251  -17.1502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6000  -14.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3179  -15.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3204  -15.9210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6055  -16.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8876  -15.9218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1743  -16.3393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9853  -11.8100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8917  -11.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8833  -12.2134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1668  -12.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4545  -12.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7422  -12.6133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7339  -13.4381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1793  -10.9638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4587  -11.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1710  -13.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6664  -12.4676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0216  -12.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6789  -11.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4545  -13.8547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0299  -13.8547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1580  -11.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3093  -13.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3093  -12.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8833  -10.5639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9331  -10.3515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1585  -11.7927    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.4462  -13.0257    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.8833  -13.0299    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4240  -15.9965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6 12  1  0
 11  5  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  1
  7  1  1  1
  8  2  1  6
  9  3  1  1
 10  4  1  6
 15 14  1  0
 16 15  1  0
 17 21  1  0
 18 17  1  0
 19 18  2  0
 20 14  1  0
 21 20  1  0
 22 16  1  0
 23 15  1  0
 24 18  1  0
 25 14  1  0
 26 22  1  0
 27 19  1  0
 28 25  1  0
 29 30  1  0
 30 24  2  0
 14 31  1  1
 25 32  1  6
  1 29  1  0
 16 33  1  1
 17 34  1  6
 15 35  1  6
 23 28  1  0
 16 17  1  0
 19 26  1  0
 27 29  2  0
 28 13  1  6
 12 36  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3526999

   ---

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: 464.51

Molecular Weight (Monoisotopic): 464.2046

AlogP: 0.15

#Rotatable Bonds: 3

Polar Surface Area: 156.91

Molecular Species: ACID

HBA: 8

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.30

CX Basic pKa: ┄

CX LogP: 0.72

CX LogD: -2.70

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.37

Np Likeness Score: 2.20

References

1. Sneitz N, Vahermo M, Mosorin J, Laakkonen L, Poirier D, Finel M..  (2013)  Regiospecificity and stereospecificity of human UDP-glucuronosyltransferases in the glucuronidation of estriol, 16-epiestriol, 17-epiestriol, and 13-epiestradiol.,  41  (3): [PMID:23288867] [10.1124/dmd.112.049072]

Source

Source(1):

• Scientific Literature