Bovine Metabolome Database: Showing metabocard for Nandrolone (BMDB0002725)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:01:26 UTC

Update Date

2020-05-11 20:55:57 UTC

BMDB ID

BMDB0002725

Secondary Accession Numbers

BMDB02725

Metabolite Identification

Common Name

Nandrolone

Description

Nandrolone, also known as decadura, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, nandrolone is considered to be a steroid. Based on a literature review a significant number of articles have been published on Nandrolone.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(17beta)-17-Hydroxyestr-4-en-3-one	ChEBI
17beta-Hydroxy-19-nor-4-androsten-3-one	ChEBI
17beta-Hydroxy-4-estren-3-one	ChEBI
17beta-Hydroxyestr-4-en-3-one	ChEBI
19-Norandrostenolone	ChEBI
19-Nortestosterone	ChEBI
4-Estren-17beta-ol-3-one	ChEBI
Decadura	Kegg
(17b)-17-Hydroxyestr-4-en-3-one	Generator
(17Β)-17-hydroxyestr-4-en-3-one	Generator
17b-Hydroxy-19-nor-4-androsten-3-one	Generator
17Β-hydroxy-19-nor-4-androsten-3-one	Generator
17b-Hydroxy-4-estren-3-one	Generator
17Β-hydroxy-4-estren-3-one	Generator
17b-Hydroxyestr-4-en-3-one	Generator
17Β-hydroxyestr-4-en-3-one	Generator
4-Estren-17b-ol-3-one	Generator
4-Estren-17β-ol-3-one	Generator
(17-beta)-17-Hydroxyestr-4-en-3-one	HMDB
17-beta-Hydroestr-4-en-3-one	HMDB
Deca-durabolin	HMDB
Durabolin	HMDB
Menidrabol	HMDB
Nandrolon	HMDB
Nandrolona	HMDB
Nandrolone base	HMDB
Nandrolone decanoate	HMDB
Nandrolone decanoic acid	HMDB
Nandrolone phenpropionate	HMDB
Nandrolonum	HMDB
Norandrostenolon	HMDB
Norandrostenolone	HMDB
Nortestonate	HMDB
Nortestosterone	HMDB
Nortestosteronum	HMDB
Oestrenolon	HMDB
17-Hydroxy-estr-4-ene-3-one	MeSH, HMDB
Estrenolone	MeSH, HMDB
17beta Hydroxy 19 nor 4 androsten 3 one	MeSH, HMDB

Chemical Formula

C₁₈H₂₆O₂

Average Molecular Weight

274.3978

Monoisotopic Molecular Weight

274.193280076

IUPAC Name

(1S,2R,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

Traditional Name

(1S,2R,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

CAS Registry Number

434-22-0

SMILES

[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]

InChI Identifier

InChI=1S/C18H26O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,13-17,20H,2-9H2,1H3/t13-,14+,15+,16-,17-,18-/m0/s1

InChI Key

NPAGDVCDWIYMMC-IZPLOLCNSA-N

Chemical Taxonomy

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-oxo-delta-4-steroid
3-oxosteroid
17-hydroxysteroid
Oxosteroid
Hydroxysteroid
Delta-4-steroid
Cyclohexenone
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-oxo Delta(4)-steroid (CHEBI:7466 )
17beta-hydroxy steroid (CHEBI:7466 )
anabolic androgenic steroid (CHEBI:7466 )
Estrane and derivatives (C07254 )
C18 steroids (estrogens) and derivatives (LMST02010044 )

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	118 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	3.09 mg/mL at 25 °C	Not Available
LogP	2.62	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	2.6	ALOGPS
logP	3.07	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	19.28	ChemAxon
pKa (Strongest Basic)	-0.88	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	79.95 m³·mol⁻¹	ChemAxon
Polarizability	32.27 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)	splash10-05i3-8950000000-2aca1e24a2ef4acf545f	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05i3-8950000000-2aca1e24a2ef4acf545f	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05i3-8950000000-2aca1e24a2ef4acf545f	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05i3-8950000000-2aca1e24a2ef4acf545f	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05i3-8950000000-2aca1e24a2ef4acf545f	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05i3-8950000000-2aca1e24a2ef4acf545f	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05i3-8950000000-2aca1e24a2ef4acf545f	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05i3-8950000000-2aca1e24a2ef4acf545f	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-1390000000-ccec1d79f2682b0d6bcd	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-014i-3459000000-2c9e474d4fe483963de2	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	splash10-004i-0090000000-494e848349f5e9b86582	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0570-1980000000-e03a1bc79e9f4e2d8260	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-2900000000-e8dd93d5cf0dff8b90e4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a5c-7900000000-71f3c599cf3161ab0eb7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-057l-9500000000-ab3f2a34ef86ef591844	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-004i-0490000000-ef50b9f0fd0a9e2b7c03	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0090000000-494e848349f5e9b86582	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0570-1890000000-f1ef53c89897edb937bd	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a5c-7900000000-3fcbdc990804e86cea69	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0a4i-3900000000-38204908207e3c492f31	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-057l-9500000000-f8e3f1dca618b5773382	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0a70-1950000000-3deed21a74589392a1e6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-057l-9500000000-1532de517e04b6798dff	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0570-1890000000-c97321edf7f62a485d35	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0a4i-3900000000-e3fa79b994c641358e40	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a5c-7900000000-05b21f3048b9a15fd44c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a6r-0090000000-a68cb7a4b0cf987e8757	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-0390000000-3e5a09a8ce0262c4d8dd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pb9-3930000000-0e574177891b374ec885	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-d6ac133b0193eab1624e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0090000000-7b428460d9c77da1b323	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-1190000000-31322ef34e235f8b8e8f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0090000000-5809628d56891b262e6f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004j-0950000000-ff92f819e00b54e35c1e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052b-2900000000-8fa1a18a876d0904eb9e	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Membrane

Biospecimen Locations

Adrenal Gland
Epidermis
Hair
Skeletal Muscle
Testis

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adrenal Gland	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Hair	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Skeletal Muscle	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Testis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0002725

DrugBank ID

DB13169

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023054

KNApSAcK ID

Not Available

Chemspider ID

9520

KEGG Compound ID

C07254

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nandrolone

METLIN ID

1434

PubChem Compound

9904

PDB ID

Not Available

ChEBI ID

7466

References

Synthesis Reference

Nomine Gerard, Bertin Daniel, Tessier Jean, Pierdet Andre, Bucourt Robert. Process for the preparation of 19-nortestosterone and compounds used in this process. 1963, US Patent 3101354A (https://patents.google.com/patent/US3101354)

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Nandrolone (BMDB0002725)

Structure for BMDB0002725 (Nandrolone)