Bovine Metabolome Database: Showing metabocard for Adrenosterone (BMDB0006772)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:25:53 UTC

Update Date

2020-04-22 15:18:33 UTC

BMDB ID

BMDB0006772

Secondary Accession Numbers

BMDB06772

Metabolite Identification

Common Name

Adrenosterone

Description

Adrenosterone, also known as Adrenosterone or NSC 12166, 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. Adrenosterone is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Adrenosterone can be biosynthesized from 11b-hydroxyandrost-4-ene-3,17-dione through its interaction with the enzyme corticosteroid 11-beta-dehydrogenase isozyme 1. In cattle, adrenosterone is involved in the metabolic pathway called the androstenedione metabolism pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
11-Keto-androstenedione	ChEBI
11-Ketoandrostenedione	ChEBI
11-oxo	ChEBI
11-Oxoandrost-4-ene-3,17-dione	ChEBI
11-Oxoandrostenedione	ChEBI
11-Oxy-4-androstenedione	ChEBI
4-Androsten-3,11,17-trione	ChEBI
Andrenosterone	ChEBI
Androst-4-ene-3,11,17-trione	ChEBI
NSC 12166	ChEBI
Reichstein's substance g	ChEBI
4-Androstene-3,11,17-trione	HMDB
Adrenosterone, 3H-labeled	HMDB

Chemical Formula

C₁₉H₂₄O₃

Average Molecular Weight

300.3921

Monoisotopic Molecular Weight

300.172544634

IUPAC Name

(1S,2R,10S,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,14,17-trione

Traditional Name

adrenosterone

CAS Registry Number

382-45-6

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C19H24O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-14,17H,3-8,10H2,1-2H3/t13-,14-,17+,18-,19-/m0/s1

InChI Key

RZRPTBIGEANTGU-IRIMSJTPSA-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-delta-4-steroid
3-oxosteroid
Oxosteroid
17-oxosteroid
11-oxosteroid
Delta-4-steroid
Cyclohexenone
Cyclic ketone
Ketone
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-hydroxy steroid (CHEBI:2495 )
Androstane and derivatives (C05285 )

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	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.42	ALOGPS
logP	3.01	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	17.99	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	51.21 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	84.27 m³·mol⁻¹	ChemAxon
Polarizability	33.28 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 - GC-MS (Non-derivatized)	splash10-004l-3910000000-dda2aae9c4577545506c	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004l-3910000000-dda2aae9c4577545506c	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fr-1590000000-60fcf2c287c8dac542ee	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0ab9-2940000000-06e07dc51a896789d933	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-001i-0290000000-a6dda3c4c0b1e8e4c477	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-001i-0090000000-572505448243920d7c46	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-001i-0190000000-6a4af6e2a1477f91dfbb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-001i-0190000000-57c8256a5ea31b9519f8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-004i-1091000000-6b6dae7a99821b529938	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-004i-1092000000-9361c41ea86f032c634b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0159-0290000000-6d600d8c52e480412d37	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0159-0290000000-af6aba5ffbd5525ba43a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0ab9-2940000000-06e07dc51a896789d933	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0596-3910000000-521e74db879ee9f81a3b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0pi0-0973000000-767c7b546b71c185a624	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0udi-0469000000-25e6987364697bc536e2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0019000000-059fceb486c74e543289	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0069000000-51d9ddcfd1d7b8a3e20c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0l7i-0291000000-7b42bb8a716d4c0700e6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0k9j-2490000000-c88e67e966734b1d65ea	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-34ecec5ab91ebc5e78dd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0090000000-4c027780977d32f6a16e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05nf-2090000000-cdcd813d0ed227d587c1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-dd82c6133109d0e6e28e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0090000000-ff5973ba5b3491dd86a7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014m-4190000000-b9abb2323ddbbd68f5ca	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0029000000-2789ee380fa1a8c91727	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0191000000-4cdffaa52886ce780121	View in MoNA