16-epiestriol-16-glucuronide

ID: ALA3527600

PubChem CID: 98049072

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

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(21(24)29)32-23-19(28)17(26)18(27)20(33-23)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:  FQYGGFDZJFIDPU-FFLBMIEMSA-N

Molfile:  

     RDKit          2D

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   20.8419  -14.8285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4959  -14.7829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3627  -16.1931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5751  -17.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8814  -16.2618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4721  -18.3044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2730  -15.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1001  -15.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5356  -16.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1397  -16.9399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3126  -16.9628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9210  -17.6907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7507  -14.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7423  -15.2304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0258  -15.6346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3134  -15.2180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6010  -15.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5928  -16.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0383  -13.9807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3176  -14.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0299  -16.4594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5255  -15.4846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8803  -15.2180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5380  -14.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3134  -16.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8886  -16.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0170  -14.8222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1679  -16.4594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1679  -15.6346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7423  -13.5808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7921  -13.3683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4556  -16.8718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0175  -14.8097    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.3051  -16.0429    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.7423  -16.0470    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.4461  -15.5263    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.1020  -17.7887    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 31  1  1
 32 28  1  0
 15 33  1  1
 16 34  1  6
 14 35  1  6
 22 27  1  0
 15 16  1  0
 18 25  1  0
 26 28  2  0
 27  1  1  1
  7 36  1  6
 12 37  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3527600

   3,17beta-dihydroxyestra-1(10),2,4-trien-16beta-yl beta-D-glucopyranosiduronic acid

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: 3.46

CX Basic pKa: ┄

CX LogP: 1.22

CX LogD: -2.17

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.37

Np Likeness Score: 2.24

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