Showing Compound Estrone (FDB012798)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:22 UTC

Update date

2019-11-26 03:07:37 UTC

Primary ID

FDB012798

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Estrone

Description

Estrone, also known as folliculin or estrovarin, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, estrone is considered to be a steroid lipid molecule. Estrone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Estrone is a potentially toxic compound.

CAS Number

53-16-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
3-Hydroxy-1,3,5(10)-estratrien-17-one	ChEBI
Follicular hormone	ChEBI
Folliculin	ChEBI
Oestrone	ChEBI
(+)-Estrone	HMDB
1,3,5(10)-Estratrien-3-ol-17-one	HMDB
3-Hydroxy-17-keto-estra-1,3,5-triene	HMDB
3-Hydroxyestra-1,3,5(10)-trien-17-one	HMDB
3-Hydroxyestra-1,3,5(10)-triene-17-one	HMDB
3-Hydroxyoestra-1,3,5(10)-trien-17-one	HMDB
D1,3,5(10)-Estratrien-3-ol-17-one	HMDB
Estrone, (+-)-isomer	HMDB
Hyrex brand OF estrone	HMDB
Estrone, (9 beta)-isomer	HMDB
Estrovarin	HMDB
Kestrone	HMDB
Wehgen	HMDB
Estrone, (8 alpha)-isomer	HMDB
Hauck brand OF estrone	HMDB
Unigen	HMDB
Vortech brand OF estrone	HMDB
1,3,5-Estratrien-3-ol-17-one	biospider
1,3,5-Oestratrien-3-ol-17-one	biospider
1,3,5(10)-Oestratrien-3-ol-17-one	biospider
3-Hydroxy-1,3,5(10)-oestratrien-17-one	biospider
3-hydroxy-estra-1,3,5(10)-trien-17-one	biospider
3-Hydroxy-oestra-1,3,5(10)-trien-17-one	biospider
3-Hydroxyestra-1,3,5(10)-17-one	biospider
3-Hydroxyestra-1,3,5(10)-trien-17-one, 9CI	db_source
3-Hydroxyestra-1(10),2,4-trien-17-one	biospider
5(10)-estratrien-17-one	biospider
Estra-1,3,5(10)-trien-17-one, 3-hydroxy-	biospider
Estra-1(10),2,4-trien-17-one, 3-hydroxy-	biospider
Estrone (usan)	biospider
Estrusol	biospider
Follestrine	biospider
Follestrol	biospider
Hormovarine	biospider
Oestrin	db_source
Oestrone, BAN	db_source
Ovifollin	biospider
Solliculin	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.0039 g/L	ALOGPS
logP	4.03	ALOGPS
logP	4.31	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	10.33	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	79.08 m³·mol⁻¹	ChemAxon
Polarizability	31.24 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	No	ChemAxon

Chemical Formula

C18H22O2

IUPAC name

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

InChI Identifier

InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1

InChI Key

DNXHEGUUPJUMQT-CBZIJGRNSA-N

Isomeric SMILES

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

Average Molecular Weight

270.3661

Monoisotopic Molecular Weight

270.161979948

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
Hydroxysteroid
17-oxosteroid
Oxosteroid
Phenanthrene
Tetralin
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Ketone
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

17-oxo steroid (CHEBI:17263 )
3-hydroxy steroid (CHEBI:17263 )
estrane (C00468 )
C18 steroids (estrogens) and derivatives (C00468 )
Estrane and derivatives (C00468 )
Estrogens (C00468 )
C18 steroids (estrogens) and derivatives (LMST02010004 )

Ontology

Psychiatric disorders:

Gastrointestinal disorders:

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Hepatic tissue

Organ and components:

Subcellular:

Biofluid and excreta:

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

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Biological role:

Molecular messenger:

Signaling molecule

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 79.96%; H 8.20%; O 11.84%	DFC
Melting Point	Mp 259°	DFC
Boiling Point	Not Available
Experimental Water Solubility	0.03 mg/mL at 25 oC	MERCK INDEX (1996)
Experimental logP	3.13	HANSCH,C ET AL. (1995)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	0
Optical Rotation	[a]D +165 (CHCl3)	DFC
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)	splash10-00di-2930000000-c99df908474247066a2b	2014-09-20	View Spectrum
GC-MS	Estrone, 1 TMS, GC-MS Spectrum	splash10-05ox-3951000000-8bc438f505b3cf49b21f	Spectrum
GC-MS	Estrone, 1 MEOX; 1 TMS, GC-MS Spectrum	splash10-003u-4942000000-a72ea34d85d9d524c247	Spectrum
GC-MS	Estrone, 1 MEOX; 1 TMS, GC-MS Spectrum	splash10-0019-8931000000-aad9803af812c7c40f53	Spectrum
GC-MS	Estrone, non-derivatized, GC-MS Spectrum	splash10-00di-2940000000-2d417e7ecb4a8b87b817	Spectrum
GC-MS	Estrone, non-derivatized, GC-MS Spectrum	splash10-00di-0980000000-5b293db89a0f2efeb784	Spectrum
GC-MS	Estrone, non-derivatized, GC-MS Spectrum	splash10-05ox-3951000000-8bc438f505b3cf49b21f	Spectrum
GC-MS	Estrone, non-derivatized, GC-MS Spectrum	splash10-003u-4942000000-a72ea34d85d9d524c247	Spectrum
GC-MS	Estrone, non-derivatized, GC-MS Spectrum	splash10-0019-8931000000-aad9803af812c7c40f53	Spectrum
Predicted GC-MS	Estrone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0adl-1970000000-871531490fb22b8fe12f	Spectrum
Predicted GC-MS	Estrone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-009t-1093000000-a8d755d13e3b819514c8	Spectrum
Predicted GC-MS	Estrone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estrone, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estrone, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estrone, TBDMS_1_2, 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)	splash10-00di-0190000000-071e67516e11357ff64e	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4j-4910000000-20e059a7c508ba492af3	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-067i-9700000000-9ff5214f08822f238fa9	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-00di-2940000000-3b9744c27d6a3d2eff6e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0ukc-2690000000-7afb48e267c7b334213b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-014i-0690000000-a76244de959b06ec896e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a59-0910000000-4a1bc1cbc90c3e5281e6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a59-0900000000-0830d4ad43804976f508	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-0390000000-41440e74b3f0b5f365d7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-0390000000-fdc0255246e3a9013d0a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0a59-2910000000-fc5173d435c3c7fc603c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00di-0390000000-25cecb1c4785e7bffd56	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0pb9-0930000000-d947dbed0baa600d21a1	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0190000000-38b40bed2e5c895d292f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0pc0-0920000000-391eea72f6dda0eaa3c2	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-0159-0900000000-350b322964f2315bf505	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-014i-0690000000-277d92852a8f35c82f11	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0002-0910000000-db57c4d24dab84acfe27	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-014i-0900000000-61f2965f743c194d4628	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0190000000-64cf013a5b0ad5e8bf56	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00fr-0590000000-40418c285df2157226dc	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fb9-6980000000-724c68b368fbe3d38f5e	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0090000000-6778bd7122813b501c1e	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0090000000-0f2e0b96bc30b346c581	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f9i-1090000000-9ccbd9f351dd1f8e52cb	2017-07-26	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50.32 MHz, DMSO-d6, 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

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

DB00655

HMDB ID

HMDB00145

CRC / DFC (Dictionary of Food Compounds) ID

HLF43-J:HLF43-J

EAFUS ID

Not Available

Dr. Duke ID

BIGG ID

KNApSAcK ID

HET ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Estrone

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-impotence	52217	An agent that enhances erectile function, treating erectile dysfunction by increasing blood flow to the penis, commonly used in managing conditions such as impotence and erectile disorders, improving sexual health and quality of life.	DUKE
Anti-menopausal	52217	An agent that alleviates menopausal symptoms, regulating hormonal balance and reducing discomfort. Therapeutically, it is used to manage hot flashes, night sweats, and mood changes, improving quality of life for menopausal women. Key medical uses include hormone replacement therapy and treatment of menopause-related disorders.	DUKE
Anti prostat adenomic	35610	An agent that inhibits the growth of prostatic adenoma cells, reducing benign prostatic hyperplasia (BPH) symptoms. It helps alleviate urinary obstruction, improving quality of life for patients with enlarged prostates, and is used to treat BPH and prevent related complications.	DUKE
Anti-vaginitic	52217	An agent that prevents or treats vaginal infections, reducing inflammation and promoting healthy vaginal flora. Therapeutically, it is used to manage vaginitis, relieving symptoms such as itching, burning, and discharge, and is commonly applied in gynecology to treat bacterial, fungal, or parasitic infections.	DUKE
Aphrodisiac		A substance that stimulates sexual desire, playing a biological role in enhancing libido. It has therapeutic applications in treating sexual dysfunction and key medical uses in managing conditions such as erectile dysfunction and low sex drive.	DUKE
Carcinogenic	50903	An agent that causes cancer, damaging cellular DNA and disrupting normal cell growth. It has no therapeutic applications, but understanding its biological role informs cancer prevention and treatment strategies, with key medical uses in oncology research and risk assessment.	DUKE
Estrogenic		An agent that mimics the effects of estrogen, regulating female reproductive processes and development. Therapeutically, estrogenic agents are used in hormone replacement therapy, contraception, and treating menopausal symptoms, as well as certain cases of osteoporosis and infertility.	DUKE
Transdermal		A route of administration where active ingredients are delivered through the skin for systemic distribution, used therapeutically to manage conditions like pain, hormone replacement, and smoking cessation, with key medical applications including patches and implants for controlled release of medications.	DUKE

Enzymes

Name	Gene Name	UniProt ID
UDP-glucuronosyltransferase 2B28	UGT2B28	Q9BY64
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
Sex hormone-binding globulin	SHBG	P04278
Estrogen receptor	ESR1	P03372
UDP-glucuronosyltransferase 2A3	UGT2A3	Q6UWM9
Cytochrome P450, family 1, subfamily A, polypeptide 1	CYP1A1	A0N0X8
Cytochrome P450 2D6	CYP2D6	Q6NWU0
Estrogen sulfotransferase	SULT1E1	P49888