| Common Name |
Nandrolone phenpropionate
| Description |
Nandrolone phenpropionate is only found in individuals that have used or taken this drug. It is a C18 steroid with androgenic and anabolic properties. It is generally prepared from alkyl ethers of estradiol to resemble testosterone but less one carbon at the 19 position. It is a schedlie III drug in the U.S. Nandrolone is an androgen receptor agonist. The drug bound to the receptor complexes which allows it to enter the nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects.
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
19NTPPChEBI
DurabolinChEBI
Nadrolone phenylpropionateChEBI
Nandrolon phenylpropionateChEBI
Nandrolone phenylpionateChEBI
Nandrolone phenylpropionateChEBI
Norandrolone phenyl propionateChEBI
Norandrostenolone phenylpropionateChEBI
Nortestosterone phenylpropionateChEBI
NPPChEBI
NTPPChEBI
Nandrolone phenpropionic acidGenerator
Nadrolone phenylpropionic acidGenerator
Nandrolon phenylpropionic acidGenerator
Nandrolone phenylpionic acidGenerator
Nandrolone phenylpropionic acidGenerator
Norandrolone phenyl propionic acidGenerator
Norandrostenolone phenylpropionic acidGenerator
Nortestosterone phenylpropionic acidGenerator
NandrolinHMDB
Testosterone phenylpropionateHMDB
17 beta-Hydroxyestr-4-en-3-one hydrocinnamateMeSH
Nandrolone phenpropionate, (17alpha)-isomerMeSH
FenobolinMeSH
NerobolylMeSH
NerobolilMeSH
Norandrolone phenylpropionateMeSH
| Chemical Formlia |
C27H34O3
| Average Molecliar Weight |
406.5571
| Monoisotopic Molecliar Weight |
406.250794954
| IUPAC Name |
(1S,2R,10R,11S,14S,15S)-15-methyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl 3-phenylpropanoate
| Traditional Name |
activin
| CAS Registry Number |
434-22-0
| SMILES |
[H][C@@]12CC[C@H](OC(=O)CCC3=CC=CC=C3)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]
| InChI Identifier |
InChI=1S/C27H34O3/c1-27-16-15-22-21-11-9-20(28)17-19(21)8-10-23(22)24(27)12-13-25(27)30-26(29)14-7-18-5-3-2-4-6-18/h2-6,17,21-25H,7-16H2,1H3/t21-,22+,23+,24-,25-,27-/m0/s1
| InChI Key |
UBWXUGDQUBIEIZ-QNTYDACNSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of organic compounds known as steroid esters. These are compounds containing a steroid moiety which bears a carboxylic acid ester group.
| Kingdom |
Organic compounds
| Super Class |
Lipids and lipid-like moleclies
| Class |
Steroids and steroid derivatives
| Sub Class |
Steroid esters
| Direct Parent |
Steroid esters
| Alternative Parents |
Estrogens and derivatives
3-oxo delta-4-steroids
Delta-4-steroids
Cyclohexenones
Benzene and substituted derivatives
Carboxylic acid esters
Monocarboxylic acids and derivatives
Organic oxides
Hydrocarbon derivatives
| Substituents |
Steroid ester
Estrogen-skeleton
3-oxo-delta-4-steroid
3-oxosteroid
Oxosteroid
Estrane-skeleton
Delta-4-steroid
Cyclohexenone
Monocyclic benzene moiety
Benzenoid
Carboxylic acid ester
Cyclic ketone
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound
| Molecliar Framework |
Aromatic homopolycyclic compounds
| External Descriptors |
3-phenylpropionate ester (CHEBI:7468 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Drug
| Biofunction |
Anabolic Agents
Androgens
Cell signaling
Fuel and energy storage
Fuel or energy source
Membrane integrity/stability
| Application |
Nutrients
Pharmaceutical
Stabilizers
Surfactants and Emlisifiers
| Cellliar locations |
Cytoplasm
Extracellliar
Membrane
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point118 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.58e-04 g/LNot Available
LogP2.62HANSCH,C ET AL. (1995)
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.000458 mg/mLALOGPS
logP4.22ALOGPS
logP5.79ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)19.28ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity118.43 m3·mol-1ChemAxon
Polarizability47.83 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
Extracellliar
Membrane
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00984
21059682
details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00984
21059682
details
|
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
DB00984
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
Not Available
| KNApSAcK ID |
Not Available
| Chemspider ID |
199761
| KEGG Compound ID |
C08155
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Nandrolone
| NuGOwiki Link |
HMDB15119
| Metagene Link |
HMDB15119
| METLIN ID |
Not Available
| PubChem Compound |
229455
| PDB ID |
Not Available
| ChEBI ID |
7468
Product: Mofegiline (hydrochloride)
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- InChem Data Sheet [Link]
|
Enzymes
- General function:
- Involved in monooxygenase activity
- Specific function:
- Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
- Gene Name:
- CYP19A1
- Uniprot ID:
- P11511
- Molecular weight:
- 57882.48
References
- Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
- General function:
- Involved in DNA binding
- Specific function:
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3
- Gene Name:
- AR
- Uniprot ID:
- P10275
- Molecular weight:
- 98987.9
References
- Cen Y, Li K, Liu XX: [Effect of nandrolone phenylpropionate on expression of hepatic albumin-mRNA and androgen receptor in burned rats]. Zhongguo Xiu Fu Chong Jian Wai Ke Za Zhi. 2003 Nov;17(6):439-41. [PubMed:14663936 ]
- Li K, Cen Y, Liu X, Luo X: [The effects of nandrolone phenylpropionate on androgen receptor of liver and sexual glands in burned rats]. Sichuan Da Xue Xue Bao Yi Xue Ban. 2003 Oct;34(4):708-10. [PubMed:14619588 ]
- Burger LL, Haisenleder DJ, Wotton GM, Aylor KW, Dalkin AC, Marshall JC: The regulation of FSHbeta transcription by gonadal steroids: testosterone and estradiol modulation of the activin intracellular signaling pathway. Am J Physiol Endocrinol Metab. 2007 Jul;293(1):E277-85. Epub 2007 Apr 3. [PubMed:17405825 ]
- Fujii Y, Kawakami S, Okada Y, Kageyama Y, Kihara K: Regulation of prostate-specific antigen by activin A in prostate cancer LNCaP cells. Am J Physiol Endocrinol Metab. 2004 Jun;286(6):E927-31. Epub 2004 Feb 3. [PubMed:14761877 ]
- Yan W, Burns KH, Matzuk MM: Genetic engineering to study testicular tumorigenesis. APMIS. 2003 Jan;111(1):174-81; discussion 182-3. [PubMed:12760377 ]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
PMID: 11373275
