Bovine Metabolome Database: Showing metabocard for Estriol (BMDB0000153)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:20:15 UTC

Update Date

2020-06-04 18:59:02 UTC

BMDB ID

BMDB0000153

Secondary Accession Numbers

BMDB00153

Metabolite Identification

Common Name

Estriol

Description

Estriol, also known as 16a,17b-estriol or ovestin, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, estriol is considered to be a steroid lipid molecule. Estriol is a drug which is used as a test to determine the general health of an unborn fetus. Estriol exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Estriol participates in a number of enzymatic reactions, within cattle. In particular, Estriol can be biosynthesized from 16a-hydroxyestrone; which is mediated by the enzyme estradiol 17-beta-dehydrogenase 1. In addition, Estriol can be biosynthesized from estradiol; which is mediated by the enzyme cytochrome P450 3A5. In cattle, estriol is involved in the metabolic pathway called the estrone metabolism pathway. Estriol is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(16alpha,17beta)-Estra-1,3,5(10)-triene-3,16,17-triol	ChEBI
1,3,5(10)-Estratriene-3,16-alpha,17beta-triol	ChEBI
16alpha,17beta-Estriol	ChEBI
16alpha-Hydroxyestradiol	ChEBI
3,16alpha,17beta-Trihydroxy-Delta(1,3,5)-estratriene	ChEBI
Deuslon-a	ChEBI
Estriel	ChEBI
Oestriol	ChEBI
Trihydroxyestrin	ChEBI
(16a,17b)-Estra-1,3,5(10)-triene-3,16,17-triol	Generator
(16Α,17β)-estra-1,3,5(10)-triene-3,16,17-triol	Generator
1,3,5(10)-Estratriene-3,16-a,17b-triol	Generator
1,3,5(10)-Estratriene-3,16-α,17β-triol	Generator
16a,17b-Estriol	Generator
16Α,17β-estriol	Generator
16a-Hydroxyestradiol	Generator
16Α-hydroxyestradiol	Generator
3,16a,17b-Trihydroxy-delta(1,3,5)-estratriene	Generator
3,16Α,17β-trihydroxy-δ(1,3,5)-estratriene	Generator
3,16a,17b-Trihydroxy-δ(1,3,5)-estratriene	HMDB
13b-Methyl-1,3,5(10)-gonatriene-3,16a,17b-triol	HMDB
16-alpha,17-beta-Estriol	HMDB
16-alpha,17-beta-Oestriol	HMDB
16-alpha-Hydroxyestradiol	HMDB
16a-Estriol	HMDB
16alpha,17beta-Oestriol	HMDB
16alpha-Hydroxy-17beta-estradiol	HMDB
16alpha-Hydroxyoestradiol	HMDB
3,16a,17b-Estriol	HMDB
3,16a,17b-Trihydroxyestra-1,3,5(10)-triene	HMDB
3,16alpha,17beta-Trihydroxy-1,3,5(10)-estratriene	HMDB
3,16alpha,17beta-Trihydroxyestra-1,3,5(10)-triene	HMDB
Aacifemine	HMDB
Colpogyn	HMDB
Colpovister	HMDB
Destriol	HMDB
Deuslon a	HMDB
Estra-1,3,5(10)-triene-3,16a,17b-triol	HMDB
Estratriol	HMDB
Follicular hormone hydrate	HMDB
Gynasan	HMDB
Hemostyptanon	HMDB
Holin V	HMDB
Hormomed	HMDB
Incurin	HMDB
Klimax e	HMDB
Klimoral	HMDB
Oekolp	HMDB
Oestratriol	HMDB
Oestriolum	HMDB
Orestin	HMDB
Orgastyptin	HMDB
Ortho-gynest	HMDB
Ovesterin	HMDB
Ovestin	HMDB
Ovestinon	HMDB
Ovestrion	HMDB
Ovo-vinces	HMDB
Theelol	HMDB
Tridestrin	HMDB
Triovex	HMDB
16-alpha-Hydroxy-estradiol	HMDB
(16beta,17beta)-Estra-1,3,5(10)-triene-3,16,17-triol	HMDB
16beta Hydroxy estradiol	HMDB
16beta-Hydroxy-estradiol	HMDB
Epiestriol	HMDB
16 alpha Hydroxy estradiol	HMDB
16alpha,17beta Estriol	HMDB
Estra-1,3,5(10)-triene-3,16beta,17beta-triol	HMDB
13beta-Methyl-1,3,5(10)-gonatriene-3,16alpha,17beta-triol	HMDB
13β-Methyl-1,3,5(10)-gonatriene-3,16α,17β-triol	HMDB
16alpha-Estriol	HMDB
16α-Estriol	HMDB
3,16alpha,17beta-Estriol	HMDB
3,16α,17β-Estriol	HMDB
3,16α,17β-Trihydroxyestra-1,3,5(10)-triene	HMDB
Estriol	HMDB

Chemical Formula

C₁₈H₂₄O₃

Average Molecular Weight

288.3814

Monoisotopic Molecular Weight

288.172544634

IUPAC Name

(1S,10R,11S,13R,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol

Traditional Name

(1S,10R,11S,13R,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol

CAS Registry Number

50-27-1

SMILES

[H][C@@]12C[C@@H](O)[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3

InChI Identifier

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

InChI Key

PROQIPRRNZUXQM-ZXXIGWHRSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrogens and derivatives

Alternative Parents

Substituents

Estrogen-skeleton
3-hydroxysteroid
17-hydroxysteroid
16-hydroxysteroid
16-alpha-hydroxysteroid
Hydroxysteroid
Phenanthrene
Tetralin
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Cyclic alcohol
Secondary alcohol
1,2-diol
Polyol
Organooxygen compound
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

17beta-hydroxy steroid (CHEBI:27974 )
3-hydroxy steroid (CHEBI:27974 )
16alpha-hydroxy steroid (CHEBI:27974 )
C18 steroids (estrogens) and derivatives (C05141 )
Estrane and derivatives (C05141 )
Estrogens (C05141 )
C18 steroids (estrogens) and derivatives (LMST02010003 )

Ontology

Status

Detected and Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Endoplasmic reticulum
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	282 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	2.45	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	2.54	ALOGPS
logP	2.67	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	10.33	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	81.27 m³·mol⁻¹	ChemAxon
Polarizability	33.08 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-005a-1983000000-2f46d0d29b48132f7670	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-4970000000-1aa2bbf3f32fd687c37d	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-005a-1983000000-2f46d0d29b48132f7670	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ab9-1390000000-492aa66975c4e026b9d8	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-009i-2033900000-46c301a46b654b6c6bf3	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4i-5900000000-2102cb581ac98fea87b0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-1900000000-1fab12be883127f80c67	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4i-5900000000-2102cb581ac98fea87b0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positive	splash10-000i-4970000000-1aa2bbf3f32fd687c37d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-000i-0390000000-891430228022fb330b42	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-7ce66600861479086f4f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-000i-1970000000-6d5c77ab4f1744109b86	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0090000000-331480c31f6585f70cf2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0zg0-0590000000-6ee9bd7dbdbd777f46a4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-2900000000-d7ae7d481cc02d1ab839	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-2920000000-d7d95b3d24e7be97e848	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-3aa436f48e23664bd455	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0190000000-b047d204e97271aa8a65	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-0490000000-c0c0bd8b1dc1381c06fa	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ufr-3950000000-b7180dbe548021fd7fc9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-743915792d6f69593b2b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0090000000-8469d578b4631e8de995	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02p0-0190000000-738399876b56d0e183d5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-843a74fabb1d0eb512a1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kr-0090000000-4e0854fb8be9cf34de97	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02br-0090000000-70686fa9219ae093945a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-1126a56061a8c854c755	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fga-0790000000-a1dba0b6195890b30d91	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6v-3910000000-64d9abb8f215c1264e1f	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-000i-3950000000-c2f0781bc5056d66aaf5	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Endoplasmic reticulum
Membrane

Biospecimen Locations

Adrenal Cortex
Adrenal Gland
Kidney
Liver
Milk
Placenta
Testis

Pathways

Name	SMPDB/Pathwhiz	KEGG
Estrone Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adrenal Cortex	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Adrenal Gland	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Milk	Detected and Quantified	0.00002843 +/- 0.00001 uM	Not Specified	Not Specified	Normal	PMID: 512140	details
Milk	Detected and Quantified	0.00003121 +/- 0.000006935 uM	Not Specified	Not Specified	Normal	PMID: 512140	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Testis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000153

DrugBank ID

DB04573

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB006781

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

27974

References

Synthesis Reference

Leeds, Norma S.; Fukushima, David K.; Gallagher, T. F. Studies of steroid ring D epoxides of enol acetates; a new synthesis of estriol and of androstane-3b,16a,17b-triol. Journal of the American Chemical Society (1954), 76 2943-8.

Material Safety Data Sheet (MSDS)

Not Available

General References

Wolford ST, Argoudelis CJ: Measurement of estrogens in cow's milk, human milk, and dairy products. J Dairy Sci. 1979 Sep;62(9):1458-63. doi: 10.3168/jds.S0022-0302(79)83446-3. [PubMed:512140 ]

Showing metabocard for Estriol (BMDB0000153)

Structure for BMDB0000153 (Estriol)