Structure Database (LMSD)

Common Name
Estriol
Systematic Name
estra-1,3,5(10)-triene-3,16,17-triol
Synonyms
LM ID
LMST02010003
Formula
Exact Mass
Calculate m/z
288.172545
Sum Composition
Status
Curated




Classification

Biological Context

Estriol is a metabolite of estradiol and a major estrogen produced in the later stages of pregnancy. In a longitudinal study in healthy pregnant women, total plasma estriol levels increased from <10 ng/ml at 8-10 weeks gestation to approximately 150 ng/ml at week 38.1 The majority of the estriol synthesized in the later stages of pregnancy originates from fetal dehydroepiandrosterone sulfate (DHEAS) and serves as a direct marker of fetal adrenal gland activity.2 Saliva contains primarily unbound and unconjugated estriol and is commonly used for monitoring estriol levels.2,3 Plasma levels of estriol in males and non-pregnant females is less than 2 ng/ml.4

This information has been provided by Cayman Chemical

References

2. Peter, M., Dörr, H.G., and Sippell, W.G. Changes in the concentrations of dehydroepiandrosterone sulfate and estriol in maternal plasma during pregnancy: A longitudinal study in healthy women throughout gestation and at term. Horm. Res. 42(6), 278-281 (1994).
4.  Steroid levels in humans. (1999).

Reactions

Filter by species:
Reactions are shown if the E.C. number of the enzyme catalysing it is annotated in the UniProt database for a species belonging to the selected taxonomic class.
Click on an edge to display the reaction(s).
Reactions graph legend

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Estrogenic Steroids. Ill. The Crystal and Molecular Structure of Estriol,
Acta Cryst B, 1969

String Representations

InChiKey (Click to copy)
PROQIPRRNZUXQM-ZXXIGWHRSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
C1C2[C@@]3([H])CC[C@]4(C)[C@@H](O)[C@H](O)C[C@@]4([H])[C@]3([H])CCC=2C=C(O)C=1

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
LIPIDBANK ID
SST0014
PubChem CID
Cayman ID
PDB ID
GuidePharm ID

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 4
Aromatic Rings 1
Rotatable Bonds 0
Van der Waals Molecular Volume 278.07
Topological Polar Surface Area 60.69
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 3.15
Molar Refractivity 81.14

Admin

Created at
-
Updated at
3rd Aug 2022