Bovine Metabolome Database: Showing metabocard for Etiocholanedione (BMDB0003769)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:06:04 UTC

Update Date

2020-04-22 15:12:44 UTC

BMDB ID

BMDB0003769

Secondary Accession Numbers

BMDB03769

Metabolite Identification

Common Name

Etiocholanedione

Description

Etiocholanedione , also known as Etiocholanedione or etiocholanedione, belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Thus, etiocholanedione is considered to be a steroid lipid molecule. Etiocholanedione is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Etiocholanedione exists in all living organisms, ranging from bacteria to humans. Etiocholanedione participates in a number of enzymatic reactions, within cattle. In particular, Etiocholanedione can be biosynthesized from androstenedione through its interaction with the enzyme 3-oxo-5-beta-steroid 4-dehydrogenase. In addition, Etiocholanedione can be converted into etiocholanolone; which is catalyzed by the enzyme aldo-keto reductase family 1 member C4. In cattle, etiocholanedione is involved in the metabolic pathway called the androstenedione metabolism pathway.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Etiocholane-3,17-dione	ChEBI
Etiocholanedione	ChEBI
(5b)-Androstane-3,17-dione	HMDB
5b-Androstane-3,17-dione	HMDB
5b-Androstanedione	HMDB
5beta-Androstane-3,17-dione	HMDB
Etiochola-3,17-dione	HMDB

Chemical Formula

C₁₉H₂₈O₂

Average Molecular Weight

288.4244

Monoisotopic Molecular Weight

288.20893014

IUPAC Name

(1S,2S,7R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-dione

Traditional Name

5-β-androstane-3,17-dione

CAS Registry Number

1229-12-5

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12,14-16H,3-11H2,1-2H3/t12-,14+,15+,16+,18+,19+/m1/s1

InChI Key

RAJWOBJTTGJROA-QJISAEMRSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

Androgen-skeleton
3-oxo-5-beta-steroid
Oxosteroid
17-oxosteroid
3-oxosteroid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

androstane-3,17-dione (CHEBI:16985 )
C19 steroids (androgens) and derivatives (C03772 )
Androstane and derivatives (C03772 )
C19 steroids (androgens) and derivatives (LMST02020058 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	3.64	Not Available

Predicted Properties

Property	Value	Source
logP	3.4	ALOGPS
logP	3.97	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	19.78	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	82.78 m³·mol⁻¹	ChemAxon
Polarizability	33.79 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 - EI-B (Non-derivatized)	splash10-0079-2960000000-ea444704310ecd83d3ce	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-052f-3921000000-17fcd3fbf7ce3dec6b0b	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0079-2960000000-ea444704310ecd83d3ce	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-052f-3921000000-17fcd3fbf7ce3dec6b0b	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03ea-0490000000-e4819053bc47c4809a6c	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0190000000-274e4abb4afd97e047bd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05a9-0490000000-ea747ee7d3b074178ffe	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0h04-2790000000-f49dc8e9045f408d3658	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-66fb88cf829fcdb74c4c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0090000000-dcc70e0ff918620e20dc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-3190000000-eb4a160989f10eb86d96	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-383f8ad782110ec64fbf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0090000000-383f8ad782110ec64fbf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f79-0090000000-0497207bd4a67a50d8d8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-a3a5ee5e1cdb4d550aac	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0h90-0970000000-66d8653b98d2df4aa327	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-1900000000-2a46c86775b66edae018	View in MoNA