16-epiestriol-3-glucuronide

ID: ALA3527099

PubChem CID: 118753251

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-FFLBMIEMSA-N

Molfile:  

     RDKit          2D

 36 40  0  0  0  0  0  0  0  0999 V2000
   11.2959  -23.0376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7423  -23.8408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7732  -25.4977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3524  -26.3436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6000  -24.2908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0713  -26.3512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3134  -23.8624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0366  -24.2641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0464  -25.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3406  -25.5173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6175  -25.1156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9061  -25.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5902  -20.5718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5820  -21.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8655  -21.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1533  -21.3840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4411  -21.7964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4327  -22.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8781  -20.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1575  -20.5593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8697  -22.6252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3650  -21.6506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7205  -21.3840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3775  -20.3219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1533  -23.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7288  -23.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8565  -20.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0082  -22.6252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0082  -21.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5820  -19.7471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6315  -19.5347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8572  -20.9758    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1450  -22.2088    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.5820  -22.2129    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.6812  -20.9946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1916  -25.1279    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
 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 31  1  1
  1 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  1
 12 36  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3527099

   ---

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