17-epiestriol-17-glucuronide

ID: ALA3527045

PubChem CID: 118753228

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)cc4CC[C@H]3[C@@H]1C[C@@H](O)[C@H]2O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C24H32O9/c1-24-7-6-13-12-5-3-11(25)8-10(12)2-4-14(13)15(24)9-16(26)21(24)33-23-19(29)17(27)18(28)20(32-23)22(30)31/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:  CZGFLAQOJPXVRV-SQFONMOTSA-N

Molfile:  

     RDKit          2D

 37 41  0  0  0  0  0  0  0  0999 V2000
    8.7662  -13.0593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7362  -11.4051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1546  -10.5519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5987  -11.3531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1996  -13.0333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2475  -12.4622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4712  -12.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4563  -11.8078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1696  -11.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8896  -11.7818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9045  -12.6088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6287  -13.0074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7226  -14.0955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7142  -14.9203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9978  -15.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2855  -14.9079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5732  -15.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5649  -16.1449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0103  -13.6707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2897  -14.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0020  -16.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4973  -15.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8526  -14.9079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5098  -13.8457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2855  -16.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8610  -16.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9889  -14.5122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1404  -16.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1404  -15.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7142  -13.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4281  -16.5615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9895  -14.4996    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2772  -15.7325    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7142  -15.7368    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8135  -14.5184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4637  -13.4583    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7189  -13.8272    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  0
  8  2  1  6
  9  3  1  1
 10  4  1  6
 14 13  1  0
 15 14  1  0
 16 20  1  0
 17 16  1  0
 18 17  2  0
 19 13  1  0
 20 19  1  0
 21 15  1  0
 22 14  1  0
 23 17  1  0
 24 13  1  0
 25 21  1  0
 26 18  1  0
 27 24  1  0
 28 29  1  0
 29 23  2  0
 13 30  1  1
 24  1  1  6
 31 28  1  0
 15 32  1  1
 16 33  1  6
 14 34  1  6
 22 27  1  0
 15 16  1  0
 18 25  1  0
 26 28  2  0
 27 35  1  6
  7 36  1  6
 12 37  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3527045

   ---

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: 0.50

#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: 3.55

CX Basic pKa: ┄

CX LogP: 1.22

CX LogD: -2.14

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