17-epiestriol-16-glucuronide

ID: ALA3526998

PubChem CID: 118753212

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-PHEYUCJMSA-N

Molfile:  

     RDKit          2D

 37 41  0  0  0  0  0  0  0  0999 V2000
   17.4138  -13.9880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0682  -13.9653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9152  -15.3874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1076  -16.8281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4335  -15.4215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9957  -17.4720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8351  -14.6949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6623  -14.6836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0880  -15.3988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6821  -16.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8549  -16.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4532  -16.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3203  -13.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3120  -14.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5955  -14.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8833  -14.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1710  -14.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1626  -15.6161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6080  -13.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8874  -13.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5997  -15.6202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0951  -14.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4504  -14.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1076  -13.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8833  -16.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4586  -16.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5866  -13.9832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7380  -15.6202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7380  -14.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3120  -12.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3617  -12.5295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0258  -16.0326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5872  -13.9707    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.8749  -15.2037    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.3120  -15.2078    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.2402  -13.9749    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.6328  -16.9373    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  6
 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  6
  7 36  1  6
 12 37  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3526998

   ---

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