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Estrone (FDB012798)

Record Information
Version1.0
Creation date2010-04-08 22:10:22 UTC
Update date2019-11-26 03:07:37 UTC
Primary IDFDB012798
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEstrone
DescriptionEstrone, 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 Number53-16-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0039 g/LALOGPS
logP4.03ALOGPS
logP4.31ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)10.33ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity79.08 m³·mol⁻¹ChemAxon
Polarizability31.24 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H22O2
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 IdentifierInChI=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 KeyDNXHEGUUPJUMQT-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 Weight270.3661
Monoisotopic Molecular Weight270.161979948
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrogens 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 FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 79.96%; H 8.20%; O 11.84%DFC
Melting PointMp 259°DFC
Boiling PointNot Available
Experimental Water Solubility0.03 mg/mL at 25 oCMERCK INDEX (1996)
Experimental logP3.13HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
Charge0
Optical Rotation[a]D +165 (CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-00di-2930000000-c99df908474247066a2b2014-09-20View Spectrum
GC-MSEstrone, 1 TMS, GC-MS Spectrumsplash10-05ox-3951000000-8bc438f505b3cf49b21fSpectrum
GC-MSEstrone, 1 MEOX; 1 TMS, GC-MS Spectrumsplash10-003u-4942000000-a72ea34d85d9d524c247Spectrum
GC-MSEstrone, 1 MEOX; 1 TMS, GC-MS Spectrumsplash10-0019-8931000000-aad9803af812c7c40f53Spectrum
GC-MSEstrone, non-derivatized, GC-MS Spectrumsplash10-00di-2940000000-2d417e7ecb4a8b87b817Spectrum
GC-MSEstrone, non-derivatized, GC-MS Spectrumsplash10-00di-0980000000-5b293db89a0f2efeb784Spectrum
GC-MSEstrone, non-derivatized, GC-MS Spectrumsplash10-05ox-3951000000-8bc438f505b3cf49b21fSpectrum
GC-MSEstrone, non-derivatized, GC-MS Spectrumsplash10-003u-4942000000-a72ea34d85d9d524c247Spectrum
GC-MSEstrone, non-derivatized, GC-MS Spectrumsplash10-0019-8931000000-aad9803af812c7c40f53Spectrum
Predicted GC-MSEstrone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0adl-1970000000-871531490fb22b8fe12fSpectrum
Predicted GC-MSEstrone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-009t-1093000000-a8d755d13e3b819514c8Spectrum
Predicted GC-MSEstrone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEstrone, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEstrone, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEstrone, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0190000000-071e67516e11357ff64e2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4j-4910000000-20e059a7c508ba492af32012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-067i-9700000000-9ff5214f08822f238fa92012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-00di-2940000000-3b9744c27d6a3d2eff6e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0ukc-2690000000-7afb48e267c7b334213b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0690000000-a76244de959b06ec896e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a59-0910000000-4a1bc1cbc90c3e5281e62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a59-0900000000-0830d4ad43804976f5082017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0390000000-41440e74b3f0b5f365d72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0390000000-fdc0255246e3a9013d0a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0a59-2910000000-fc5173d435c3c7fc603c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0390000000-25cecb1c4785e7bffd562017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0pb9-0930000000-d947dbed0baa600d21a12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-0190000000-38b40bed2e5c895d292f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0pc0-0920000000-391eea72f6dda0eaa3c22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0159-0900000000-350b322964f2315bf5052021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-014i-0690000000-277d92852a8f35c82f112021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0002-0910000000-db57c4d24dab84acfe272021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-014i-0900000000-61f2965f743c194d46282021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0190000000-64cf013a5b0ad5e8bf562017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fr-0590000000-40418c285df2157226dc2017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-6980000000-724c68b368fbe3d38f5e2017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-6778bd7122813b501c1e2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-0f2e0b96bc30b346c5812017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f9i-1090000000-9ccbd9f351dd1f8e52cb2017-07-26View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 50.32 MHz, DMSO-d6, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Spectrum
ChemSpider ID5660
ChEMBL IDCHEMBL1405
KEGG Compound IDC00468
Pubchem Compound ID5870
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB00655
HMDB IDHMDB00145
CRC / DFC (Dictionary of Food Compounds) IDHLF43-J:HLF43-J
EAFUS IDNot Available
Dr. Duke IDESTRONE
BIGG ID35059
KNApSAcK IDC00003663
HET IDJ3Z
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDEstrone
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti impotence52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti menopausal52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti prostat adenomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti vaginitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
aphrodisiacDUKE
carcinogenic50903 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.DUKE
estrogenicDUKE
transdermalDUKE
Enzymes
NameGene NameUniProt ID
UDP-glucuronosyltransferase 2B28UGT2B28Q9BY64
UDP-glucuronosyltransferase 2B4UGT2B4P06133
UDP-glucuronosyltransferase 1-4UGT1A4P22310
UDP-glucuronosyltransferase 2B10UGT2B10P36537
UDP-glucuronosyltransferase 2B7UGT2B7P16662
UDP-glucuronosyltransferase 2B15UGT2B15P54855
UDP-glucuronosyltransferase 2A1UGT2A1Q9Y4X1
UDP-glucuronosyltransferase 1-1UGT1A1P22309
UDP-glucuronosyltransferase 1-9UGT1A9O60656
UDP-glucuronosyltransferase 1-8UGT1A8Q9HAW9
UDP-glucuronosyltransferase 1-3UGT1A3P35503
UDP-glucuronosyltransferase 1-10UGT1A10Q9HAW8
UDP-glucuronosyltransferase 2B17UGT2B17O75795
UDP-glucuronosyltransferase 1-6UGT1A6P19224
UDP-glucuronosyltransferase 1-5UGT1A5P35504
UDP-glucuronosyltransferase 2B11UGT2B11O75310
UDP-glucuronosyltransferase 1-7UGT1A7Q9HAW7
Sex hormone-binding globulinSHBGP04278
Estrogen receptorESR1P03372
UDP-glucuronosyltransferase 2A3UGT2A3Q6UWM9
Cytochrome P450, family 1, subfamily A, polypeptide 1CYP1A1A0N0X8
Cytochrome P450 2D6CYP2D6Q6NWU0
Estrogen sulfotransferaseSULT1E1P49888
Pathways
NameSMPDB LinkKEGG Link
Androgen and Estrogen MetabolismSMP00068 map00150
Sulfate/Sulfite MetabolismSMP00041 map00920
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.