16alpha-Hydroxy-17alpha-estradiol

ID: ALA1908074

Cas Number: 547-81-9

PubChem CID: 68929

Product Number: E336722, Order Now?

Max Phase: Phase

Molecular Formula: C18H24O3

Molecular Weight: 288.39

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Epioestriol | NSC-26646 | NSC-758892 | Epiestriol|16-Epiestriol|547-81-9|Epioestriol|Actriol|16b-hydroxyestradiol|Epiestriolum|Epioestriolum|16-Epiestratriol|16beta-Hydroxyestradiol|16-epi-Estriol|16b,17b-Estriol|(8R,9S,13S,14S,16S,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,16,17-triol|CHEBI:87620|NSC-26646|8XZ32LI44K|NSC-758892|Estra-1,3,5(10)-triene-3,16beta,17beta-triol|Estra-1,3.5(10)-triene-3,16beta,17beta-triol|Epiestriolo|Estriol Impurity F|(8R,9S,13S,14Show More⌵

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

Standard InChI:  InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16+,17+,18+/m1/s1

Standard InChI Key:  PROQIPRRNZUXQM-ZMSHIADSSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  1  0  0  0  0  0999 V2000
   10.1822   -5.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1781   -6.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5117   -6.2869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7755   -6.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0580   -6.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9920   -4.9241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1151   -6.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0094   -7.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4441   -5.4696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3283   -4.7567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6105   -5.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5171   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3604   -5.9597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7230   -7.6440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2536   -7.5979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5560   -7.1478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6046   -6.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2563   -4.2890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2825   -5.3652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8002   -7.5296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7458   -6.7958    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4583   -5.5583    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1708   -6.8000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2138   -4.1098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4 11  1  0
  5  4  1  0
  6  1  1  0
  7  2  1  0
  8  5  2  0
  9  6  1  0
 10  1  1  0
 11 10  1  0
 12  3  1  0
 13  5  1  0
 14 12  1  0
 15  8  1  0
 16 17  1  0
 17 13  2  0
  1 18  1  1
  9 19  1  1
 20 16  1  0
  7  9  1  0
  3  4  1  0
 14  8  1  0
 15 16  2  0
  4 21  1  6
  3 22  1  1
  2 23  1  6
  6 24  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1908074

   16-Epiestriol

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 288.39

Molecular Weight (Monoisotopic): 288.1725

AlogP: 2.58

#Rotatable Bonds: ┄

Polar Surface Area: 60.69

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.33

CX Basic pKa: ┄

CX LogP: 2.67

CX LogD: 2.67

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.69

Np Likeness Score: 2.51

References

1. Tukey RH, Strassburg CP..  (2000)  Human UDP-glucuronosyltransferases: metabolism, expression, and disease.,  40  (1): [PMID:10836148] [10.1146/annurev.pharmtox.40.1.581]

2. Tukey RH, Strassburg CP..  (2000)  Human UDP-glucuronosyltransferases: metabolism, expression, and disease.,  40  (1): [PMID:10836148] [10.1146/annurev.pharmtox.40.1.581]

3. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

4. 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(2):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names