AFCDB: Estriol (FDB006781)

Record Information

Version

1.0

Creation date

2010-04-08 22:07:18 UTC

Update date

2019-11-26 03:01:18 UTC

Primary ID

FDB006781

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Estriol

Description

Estriol, also known as estriel or 16a,17b-estriol, 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 very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Estriol is a potentially toxic compound.

CAS Number

50-27-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
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	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C18H24O3

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

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

Isomeric 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

Average Molecular Weight

288.3814

Monoisotopic Molecular Weight

288.172544634

Classification

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

Ingestion

Source:

Biological:

Plant:

Fabaceae

Biological location:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

System process:

Reproduction

Cellular process:

Cell signaling

Role

Biological role:

Molecular messenger:

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	282 oC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	2.45	HANSCH,C ET AL. (1995)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	0
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-000i-3950000000-c2f0781bc5056d66aaf5	2014-09-20	View Spectrum
GC-MS	Estriol, 3 TMS, GC-MS Spectrum	splash10-005a-1983000000-2f46d0d29b48132f7670	Spectrum
GC-MS	Estriol, non-derivatized, GC-MS Spectrum	splash10-000i-4970000000-1aa2bbf3f32fd687c37d	Spectrum
GC-MS	Estriol, non-derivatized, GC-MS Spectrum	splash10-005a-1983000000-2f46d0d29b48132f7670	Spectrum
Predicted GC-MS	Estriol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ab9-1390000000-492aa66975c4e026b9d8	Spectrum
Predicted GC-MS	Estriol, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-009i-2033900000-46c301a46b654b6c6bf3	Spectrum
Predicted GC-MS	Estriol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol, TBDMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4i-5900000000-2102cb581ac98fea87b0	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-1900000000-1fab12be883127f80c67	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4i-5900000000-2102cb581ac98fea87b0	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positive	splash10-000i-4970000000-1aa2bbf3f32fd687c37d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-000i-0390000000-891430228022fb330b42	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-7ce66600861479086f4f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-000i-1970000000-6d5c77ab4f1744109b86	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0090000000-331480c31f6585f70cf2	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0zg0-0590000000-6ee9bd7dbdbd777f46a4	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-2900000000-d7ae7d481cc02d1ab839	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-2920000000-d7d95b3d24e7be97e848	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-3aa436f48e23664bd455	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0190000000-b047d204e97271aa8a65	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-0490000000-c0c0bd8b1dc1381c06fa	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ufr-3950000000-b7180dbe548021fd7fc9	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-743915792d6f69593b2b	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0090000000-8469d578b4631e8de995	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02p0-0190000000-738399876b56d0e183d5	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-843a74fabb1d0eb512a1	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kr-0090000000-4e0854fb8be9cf34de97	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02br-0090000000-70686fa9219ae093945a	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-1126a56061a8c854c755	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fga-0790000000-a1dba0b6195890b30d91	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6v-3910000000-64d9abb8f215c1264e1f	2021-09-22	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)		Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

27974

Phenol-Explorer ID

Not Available

DrugBank ID

DB04573

HMDB ID

HMDB00153

CRC / DFC (Dictionary of Food Compounds) ID

GQH02-E:GQH02-E

EAFUS ID

Not Available

Dr. Duke ID

ESTRIOL|ESTROL

BIGG ID

45207

KNApSAcK ID

Not Available

HET ID

ESL

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Estriol

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti estrogenic	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
anti hot-flash			DUKE
anti menopausal	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
estrogenic			DUKE
transdermal			DUKE

Enzymes

Name	Gene Name	UniProt ID
UDP-glucuronosyltransferase 2B28	UGT2B28	Q9BY64
Estrogen receptor beta	ESR2	Q92731
UDP-glucuronosyltransferase 2B4	UGT2B4	P06133
UDP-glucuronosyltransferase 1-4	UGT1A4	P22310
UDP-glucuronosyltransferase 2B10	UGT2B10	P36537
UDP-glucuronosyltransferase 2B7	UGT2B7	P16662
UDP-glucuronosyltransferase 2B15	UGT2B15	P54855
UDP-glucuronosyltransferase 2A1	UGT2A1	Q9Y4X1
UDP-glucuronosyltransferase 1-1	UGT1A1	P22309
UDP-glucuronosyltransferase 1-9	UGT1A9	O60656
UDP-glucuronosyltransferase 1-8	UGT1A8	Q9HAW9
UDP-glucuronosyltransferase 1-3	UGT1A3	P35503
UDP-glucuronosyltransferase 1-10	UGT1A10	Q9HAW8
UDP-glucuronosyltransferase 2B17	UGT2B17	O75795
UDP-glucuronosyltransferase 1-6	UGT1A6	P19224
UDP-glucuronosyltransferase 1-5	UGT1A5	P35504
UDP-glucuronosyltransferase 2B11	UGT2B11	O75310
UDP-glucuronosyltransferase 1-7	UGT1A7	Q9HAW7
Estrogen receptor	ESR1	P03372
UDP-glucuronosyltransferase 2A3	UGT2A3	Q6UWM9

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Estriol (FDB006781)

Structure for FDB006781 (Estriol)