Showing Compound 16alpha-Hydroxyestrone (FDB021959)

Record Information

Version

1.0

Creation date

2011-09-21 00:05:52 UTC

Update date

2015-10-09 22:30:49 UTC

Primary ID

FDB021959

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

16alpha-Hydroxyestrone

Description

Estrone (also oestrone) is an estrogenic hormone secreted by the ovary. Its molecular formula is C18H22O2. estrone has a melting point of 254.5 degrees Celsius. estrone is one of the three estrogens, which also include estriol and estradiol. estrone is the least prevalent of the three hormones, estradiol being prevalent almost always in a female body, estriol being prevalent primarily during pregnancy. estrone sulfate is relevant to health and disease due to its conversion to estrone sulfate, a long-lived derivative of estrone. estrone sulfate acts as a pool of estrone which can be converted as needed to the more active estradiol. [HMDB]

CAS Number

566-76-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
16 alpha OHE	ChEBI
3,16alpha-Dihydroxy-1,3,5(10)-estratrien-17-one	ChEBI
3,16alpha-Dihydroxyestra-1,3,5(10)-trien-17-one	ChEBI
Estra-1,3,5(10)-triene-3,16alpha-diol-17-one	ChEBI
16 a OHE	Generator
16 Α ohe	Generator
3,16a-Dihydroxy-1,3,5(10)-estratrien-17-one	Generator
3,16Α-dihydroxy-1,3,5(10)-estratrien-17-one	Generator
3,16a-Dihydroxyestra-1,3,5(10)-trien-17-one	Generator
3,16Α-dihydroxyestra-1,3,5(10)-trien-17-one	Generator
Estra-1,3,5(10)-triene-3,16a-diol-17-one	Generator
Estra-1,3,5(10)-triene-3,16α-diol-17-one	Generator
16 alpha-Hydroxyestrone	HMDB
3,16a-Dihydroxy-estra-1,3,5(10)-trien-17-one	HMDB
16 beta-Hydroxyestrone	HMDB
16-alpha-Hydroxyestrone	HMDB
16-Hydroxyestrone	HMDB
16 α ohe	Generator
16-alpha-hydroxyestrone	hmdb
16a-Hydroxyestrone	hmdb
16α-hydroxyestrone	Generator
3,16α-dihydroxy-1,3,5(10)-estratrien-17-one	Generator
3,16α-dihydroxyestra-1,3,5(10)-trien-17-one	Generator

Predicted Properties

Property	Value	Source
Water Solubility	0.047 g/L	ALOGPS
logP	2.45	ALOGPS
logP	3.44	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	10.33	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	80.57 m³·mol⁻¹	ChemAxon
Polarizability	32.06 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

C18H22O3

IUPAC name

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

InChI Identifier

InChI=1S/C18H22O3/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/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,18+/m1/s1

InChI Key

WPOCIZJTELRQMF-QFXBJFAPSA-N

Isomeric SMILES

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

Average Molecular Weight

286.3655

Monoisotopic Molecular Weight

286.15689457

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
16-alpha-hydroxysteroid
16-hydroxysteroid
Phenanthrene
Tetralin
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Cyclic alcohol
Secondary alcohol
Ketone
Carbonyl group
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

16alpha-hydroxy steroid (CHEBI:776 )
C18 steroids (estrogens) and derivatives (LMST02010041 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Hepatic tissue

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

Biological role:

Molecular messenger:

Industrial application:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
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
GC-MS	16alpha-Hydroxyestrone, 1 MEOX; 2 TMS, GC-MS Spectrum	splash10-0019-3941100000-3a930f8cc95b733c8653	Spectrum
GC-MS	16alpha-Hydroxyestrone, 1 MEOX; 2 TMS, GC-MS Spectrum	splash10-0019-3941100000-3e52ec60bd9142c09b74	Spectrum
GC-MS	16alpha-Hydroxyestrone, non-derivatized, GC-MS Spectrum	splash10-0019-3941100000-3a930f8cc95b733c8653	Spectrum
GC-MS	16alpha-Hydroxyestrone, non-derivatized, GC-MS Spectrum	splash10-0019-3941100000-3e52ec60bd9142c09b74	Spectrum
Predicted GC-MS	16alpha-Hydroxyestrone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ab9-2690000000-4da4066a9998d4bb7152	Spectrum
Predicted GC-MS	16alpha-Hydroxyestrone, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0gj1-1193300000-a36ac7539d25b407ca9f	Spectrum
Predicted GC-MS	16alpha-Hydroxyestrone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	16alpha-Hydroxyestrone, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	16alpha-Hydroxyestrone, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	16alpha-Hydroxyestrone, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	16alpha-Hydroxyestrone, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	16alpha-Hydroxyestrone, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	16alpha-Hydroxyestrone, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	16alpha-Hydroxyestrone, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	16alpha-Hydroxyestrone, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	16alpha-Hydroxyestrone, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	16alpha-Hydroxyestrone, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	16alpha-Hydroxyestrone, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-ea49b0e7c1a26f8807b3	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ap0-0490000000-7a9632ca2f7369b28ad3	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gb9-7980000000-f674402195ec376faeb7	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-91f32a5e866ea149a4a4	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0090000000-f8524ff8a5fae66251ad	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02dl-1090000000-5ac386a35fc2bb3cc1f0	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-8269f9806e3a6460adb9	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00ks-0590000000-2d8e09d2baef368efec1	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dj-0920000000-bce8e0246e58d9e59bbd	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-fcaf0435bbf678a207f7	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0090000000-48bccddc063fe7e2f998	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02di-0090000000-080f7d164203318ad338	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