estriol (CHEBI:27974)

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CHEBI:27974 - estriol

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ChEBI Name	estriol

ChEBI ID	CHEBI:27974

Definition	A 3-hydroxy steroid that is estra-1,3,5(10)-trien-3-ol substituted by additional hydroxy groups at positions 16 and 17 (16α,17β-stereoisomer).

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:42467, CHEBI:4869, CHEBI:23969

Supplier Information	ChemicalBook:CB75477611, ChemicalBook:CB1687589, eMolecules:494761, eMolecules:29549880, Selleckchem:Estriol(Oestriol), ZINC000003815418

Download	Molfile XML SDF

more structures >>

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45 48 0 0 1 0 999 V2000

2.7980 1.0871 0.1542 C 0 0 0 0 0 0 0 0 0 0 0 0

1.1730 -1.6852 0.8306 C 0 0 0 0 0 0 0 0 0 0 0 0

1.8527 2.7443 -1.4452 C 0 0 2 0 0 0 0 0 0 0 0 0

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3.1507 2.3396 -0.6963 C 0 0 2 0 0 0 0 0 0 0 0 0

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-1.4775 0.6407 -0.9813 C 0 0 0 0 0 0 0 0 0 0 0 0

0.1923 -2.6331 1.5758 C 0 0 0 0 0 0 0 0 0 0 0 0

1.6491 4.1550 -1.5529 O 0 0 0 0 0 0 0 0 0 0 0 0

4.2145 2.0795 -1.6138 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.2343 -2.6095 1.1443 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.1024 -1.7482 -0.1541 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.1179 -3.5470 1.7349 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.9732 -2.6763 0.4400 C 0 0 0 0 0 0 0 0 0 0 0 0

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-4.2740 -4.4167 1.8999 O 0 0 0 0 0 0 0 0 0 0 0 0

0.4862 -0.3622 0.3915 C 0 0 2 0 0 0 0 0 0 0 0 0

0.1777 0.1124 1.3261 H 0 0 0 0 0 0 0 0 0 0 0 0

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0.7085 1.9951 -0.6984 C 0 0 2 0 0 0 0 0 0 0 0 0

0.2349 2.8320 0.5496 C 0 0 0 0 0 0 0 0 0 0 0 0

1.4176 0.6373 -0.3784 C 0 0 1 0 0 0 0 0 0 0 0 0

1.6584 0.1112 -1.3150 H 0 0 0 0 0 0 0 0 0 0 0 0

3.5494 0.2980 0.0607 H 0 0 0 0 0 0 0 0 0 0 0 0

2.7284 1.3471 1.2141 H 0 0 0 0 0 0 0 0 0 0 0 0

2.0186 -1.4683 1.4912 H 0 0 0 0 0 0 0 0 0 0 0 0

1.5832 -2.1975 -0.0448 H 0 0 0 0 0 0 0 0 0 0 0 0

1.9221 2.3855 -2.4791 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.0483 2.5841 -1.8779 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.1593 1.2450 -2.5657 H 0 0 0 0 0 0 0 0 0 0 0 0

3.4816 3.1525 -0.0443 H 0 0 0 0 0 0 0 0 0 0 0 0

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-2.2051 0.4186 -1.7651 H 0 0 0 0 0 0 0 0 0 0 0 0

0.5815 -3.6519 1.4845 H 0 0 0 0 0 0 0 0 0 0 0 0

0.2103 -2.3779 2.6396 H 0 0 0 0 0 0 0 0 0 0 0 0

2.4296 4.5085 -2.0260 H 0 0 0 0 0 0 0 0 0 0 0 0

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23 21 1 0 0 0 0

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17 19 1 0 0 0 0

17 2 1 0 0 0 0

21 3 1 0 0 0 0

21 4 1 0 0 0 0

5 1 1 0 0 0 0

19 6 1 0 0 0 0

19 7 1 0 0 0 0

2 8 1 0 0 0 0

3 9 1 0 0 0 0

5 10 1 0 0 0 0

6 11 4 0 0 0 0

6 12 4 0 0 0 0

11 13 4 0 0 0 0

12 14 4 0 0 0 0

13 15 4 0 0 0 0

15 16 1 0 0 0 0

3 5 1 0 0 0 0

4 7 1 0 0 0 0

8 11 1 0 0 0 0

14 15 4 0 0 0 0

17 18 1 0 0 0 0

19 20 1 0 0 0 0

21 22 1 0 0 0 0

23 24 1 0 0 0 0

1 25 1 0 0 0 0

1 26 1 0 0 0 0

2 27 1 0 0 0 0

2 28 1 0 0 0 0

3 29 1 0 0 0 0

4 30 1 0 0 0 0

4 31 1 0 0 0 0

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7 33 1 0 0 0 0

7 34 1 0 0 0 0

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12 39 1 0 0 0 0

13 40 1 0 0 0 0

14 41 1 0 0 0 0

16 42 1 0 0 0 0

22 43 1 0 0 0 0

22 44 1 0 0 0 0

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reading 45 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

45 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

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Wikipedia	License
Estriol (E3), also spelled oestriol, is a steroid, a weak estrogen, and a minor female sex hormone. It is one of three major endogenous estrogens, the others being estradiol and estrone. Levels of estriol in women who are not pregnant are almost undetectable. However, during pregnancy, estriol is synthesized in very high quantities by the placenta and is the most produced estrogen in the body by far, although circulating levels of estriol are similar to those of other estrogens due to a relatively high rate of metabolism and excretion. Relative to estradiol, both estriol and estrone have far weaker activity as estrogens. In addition to its role as a natural hormone, estriol is used as a medication, for instance in menopausal hormone therapy; for information on estriol as a medication, see the estriol (medication) article.
Read full article at Wikipedia

Formula

C18H24O3

Net Charge

Average Mass

288.38140

Monoisotopic Mass

288.17254

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

InChIKey

PROQIPRRNZUXQM-ZXXIGWHRSA-N

SMILES

[H][C@]12CC[C@]3(C)[C@@H](O)[C@H](O)C[C@@]3([H])[C@]1([H])CCc1cc(O)ccc21

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Homo sapiens (NCBI:txid9606)	See: DOI

Roles Classification
Biological Role(s):	estrogen A hormone that stimulates or controls the development and maintenance of female sex characteristics in mammals by binding to oestrogen receptors. The oestrogens are named for their importance in the oestrous cycle. The oestrogens that occur naturally in the body, notably estrone, estradiol, estriol, and estetrol are steroids. Other compounds with oestrogenic activity are produced by plants (phytoestrogens) and fungi (mycoestrogens); synthetic compounds with oestrogenic activity are known as xenoestrogens. human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). human xenobiotic metabolite Any human metabolite produced by metabolism of a xenobiotic compound in humans. mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	estriol (CHEBI:27974) has parent hydride estrane (CHEBI:23966) estriol (CHEBI:27974) has role estrogen (CHEBI:50114) estriol (CHEBI:27974) has role human metabolite (CHEBI:77746) estriol (CHEBI:27974) has role human xenobiotic metabolite (CHEBI:76967) estriol (CHEBI:27974) has role mouse metabolite (CHEBI:75771) estriol (CHEBI:27974) is a 16α-hydroxy steroid (CHEBI:16799) estriol (CHEBI:27974) is a 17β-hydroxy steroid (CHEBI:35343) estriol (CHEBI:27974) is a 3-hydroxy steroid (CHEBI:36834)

Incoming	3-(allyloxy)estra-1,3,5(10)-triene-16α,17β-diol (CHEBI:79756) has functional parent estriol (CHEBI:27974) 6-ketoestriol (CHEBI:145763) has functional parent estriol (CHEBI:27974) estriol 16-O-(β-D-glucuronide) (CHEBI:766) has functional parent estriol (CHEBI:27974) estriol 3-O-(β-D-glucuronide) (CHEBI:45869) has functional parent estriol (CHEBI:27974)

IUPAC Name

estra-1,3,5(10)-triene-3,16α,17β-triol

Synonyms	Sources
(16α,17β)-estra-1,3,5(10)-triene-3,16,17-triol	NIST Chemistry WebBook
1,3,5(10)-Estratriene-3,16-alpha,17beta-triol	KEGG COMPOUND
16α,17β-estriol	UniProt
16α-hydroxyestradiol	NIST Chemistry WebBook
3,16α,17β-trihydroxy-Δ^1,3,5-estratriene	NIST Chemistry WebBook
Estriol	KEGG COMPOUND
ESTRIOL	PDBeChem
oestriol	NIST Chemistry WebBook
Östriol	ChEBI
trihydroxyestrin	NIST Chemistry WebBook

Brand Names	Sources
Deuslon-A	DrugBank
Estriel	DrugBank

Manual Xrefs	Databases
1907	VSDB
3187	DrugCentral
C05141	KEGG COMPOUND
D00185	KEGG DRUG
DB04573	DrugBank
ESL	PDBeChem
Estriol	Wikipedia
ESTRIOL	MetaCyc
HMDB0000153	HMDB
LMST02010003	LIPID MAPS
LSM-2368	LINCS
View more database links

Registry Numbers	Types	Sources
2508172	Reaxys Registry Number	Reaxys
50-27-1	CAS Registry Number	KEGG COMPOUND
50-27-1	CAS Registry Number	ChemIDplus
50-27-1	CAS Registry Number	NIST Chemistry WebBook

Citations

Olsen RN, Dunsmoor-Su R, Capurro D, McMahon K, Gravett MG (2014)
Correlation between spontaneous preterm birth and mid-trimester maternal serum estriol.
The journal of maternal-fetal & neonatal medicine : the official journal of the European Association of Perinatal Medicine, the Federation of Asia and Oceania Perinatal Societies, the International Society of Perinatal Obstetricians 27, 376-380 [PubMed:23777262]
[show Abstract]

Reyes-Romero MA (2001)
The physiological role of estriol during human fetal development is to act as antioxidant at lipophilic milieus of the central nervous system.
Medical hypotheses 56, 107-109 [PubMed:11133265]
[show Abstract]

Pope A, Pritchard K, Williams A, Roberts A, Hackett JR, Mandecki W, Johnson KS (1996)
In vitro selection of a high affinity antibody to oestradiol using a phage display human antibody library.
Immunotechnology : an international journal of immunological engineering 2, 209-217 [PubMed:9373313]
[show Abstract]

Last Modified

20 January 2020

ChEBI

CHEBI:27974 - estriol

Objective

Methods

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