Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:51 UTC |
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Update Date | 2022-03-07 02:51:52 UTC |
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HMDB ID | HMDB0015119 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Nandrolone phenpropionate |
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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 schedule 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. |
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Structure | [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=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 |
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Synonyms | Value | Source |
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19NTPP | ChEBI | Durabolin | ChEBI | Nadrolone phenylpropionate | ChEBI | Nandrolon phenylpropionate | ChEBI | Nandrolone phenylpionate | ChEBI | Nandrolone phenylpropionate | ChEBI | Norandrolone phenyl propionate | ChEBI | Norandrostenolone phenylpropionate | ChEBI | Nortestosterone phenylpropionate | ChEBI | NPP | ChEBI | NTPP | ChEBI | Nadrolone phenylpropionic acid | Generator | Nandrolon phenylpropionic acid | Generator | Nandrolone phenylpionic acid | Generator | Nandrolone phenylpropionic acid | Generator | Norandrolone phenyl propionic acid | Generator | Norandrostenolone phenylpropionic acid | Generator | Nortestosterone phenylpropionic acid | Generator | Nandrolone phenpropionic acid | Generator | Nandrolin | HMDB | Testosterone phenylpropionate | HMDB | 17 beta-Hydroxyestr-4-en-3-one hydrocinnamate | HMDB | Nandrolone phenpropionate, (17alpha)-isomer | HMDB | Fenobolin | HMDB | Nerobolyl | HMDB | Nerobolil | HMDB | Norandrolone phenylpropionate | HMDB |
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Chemical Formula | C27H34O3 |
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Average Molecular Weight | 406.5571 |
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Monoisotopic Molecular Weight | 406.250794954 |
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IUPAC Name | (1S,2R,10R,11S,14S,15S)-15-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl 3-phenylpropanoate |
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Traditional Name | (1S,2R,10R,11S,14S,15S)-15-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl 3-phenylpropanoate |
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CAS Registry Number | 62-90-8 |
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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] |
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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 |
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InChI Key | UBWXUGDQUBIEIZ-QNTYDACNSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Steroid esters |
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Direct Parent | Steroid esters |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic homopolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 118 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.00046 g/L | Not Available | LogP | 2.62 | HANSCH,C ET AL. (1995) |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Nandrolone phenpropionate,1TMS,isomer #1 | C[C@]12CC[C@@H]3[C@H]4CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC[C@@H]2OC(=O)CCC1=CC=CC=C1 | 3520.5 | Semi standard non polar | 33892256 | Nandrolone phenpropionate,1TMS,isomer #1 | C[C@]12CC[C@@H]3[C@H]4CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC[C@@H]2OC(=O)CCC1=CC=CC=C1 | 3392.6 | Standard non polar | 33892256 | Nandrolone phenpropionate,1TMS,isomer #1 | C[C@]12CC[C@@H]3[C@H]4CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC[C@@H]2OC(=O)CCC1=CC=CC=C1 | 4113.0 | Standard polar | 33892256 | Nandrolone phenpropionate,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC[C@H]2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OC(=O)CCC3=CC=CC=C3)CC[C@@H]12 | 3798.8 | Semi standard non polar | 33892256 | Nandrolone phenpropionate,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC[C@H]2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OC(=O)CCC3=CC=CC=C3)CC[C@@H]12 | 3630.9 | Standard non polar | 33892256 | Nandrolone phenpropionate,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC[C@H]2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OC(=O)CCC3=CC=CC=C3)CC[C@@H]12 | 4237.3 | Standard polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Nandrolone phenpropionate GC-MS (Non-derivatized) - 70eV, Positive | splash10-056u-2794000000-8a406f2131925f7d78d7 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Nandrolone phenpropionate GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Nandrolone phenpropionate GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nandrolone phenpropionate 10V, Positive-QTOF | splash10-0a4i-2693800000-014d5a8f5785d5fa2138 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nandrolone phenpropionate 20V, Positive-QTOF | splash10-0a59-2891000000-0d191fd67047632bac0b | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nandrolone phenpropionate 40V, Positive-QTOF | splash10-002f-2290000000-d1eb49bea81bc4fe8fec | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nandrolone phenpropionate 10V, Negative-QTOF | splash10-0a4i-0250900000-73ea898c756aee0d065d | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nandrolone phenpropionate 20V, Negative-QTOF | splash10-05fr-0491200000-c48f4cd0cb4d262db924 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nandrolone phenpropionate 40V, Negative-QTOF | splash10-006x-2290000000-2d0ca51aad14a4610e02 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nandrolone phenpropionate 10V, Positive-QTOF | splash10-0a4i-2290300000-bac5d57e78f5058c299b | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nandrolone phenpropionate 20V, Positive-QTOF | splash10-0a4l-5931100000-59cd27d9e64a7d2840f5 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nandrolone phenpropionate 40V, Positive-QTOF | splash10-0a4u-3920000000-ff8ab93696f1c30ae190 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nandrolone phenpropionate 10V, Negative-QTOF | splash10-0a4i-0000900000-c12aa2fec47362dfe817 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nandrolone phenpropionate 20V, Negative-QTOF | splash10-0a4i-2311900000-d39466b8e277a338d135 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nandrolone phenpropionate 40V, Negative-QTOF | splash10-004i-9707100000-32c75e3ec9135a8c9585 | 2021-10-11 | Wishart Lab | View Spectrum |
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