| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:48:00 UTC |
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| Update Date | 2020-06-04 20:42:59 UTC |
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| BMDB ID | BMDB0001830 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Progesterone |
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| Description | Progesterone, also known as gesterol or corlutin, belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. Thus, progesterone is considered to be a steroid lipid molecule. Progesterone is a drug which is used for progesterone supplementation or replacement as part of an assisted reproductive technology (art) treatment for infertile women with progesterone deficiency and for the treatment of secondary amenorrhea. also used for the reduction of the incidence of endometrial hyperplasia and the attendant risk of endometrial carcinoma in postmenopausal women receiving estrogen replacement therapy, as well as treatment of abnormal uterine bleeding due to hormonal imbalance in the absence of organic pathology such as fibroids or uterine cancer. Progesterone exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Progesterone exists in all living organisms, ranging from bacteria to humans. Progesterone participates in a number of enzymatic reactions, within cattle. In particular, Progesterone can be converted into deoxycorticosterone; which is mediated by the enzyme steroid 21-hydroxylase. In addition, Progesterone can be biosynthesized from pregnenolone; which is mediated by the enzyme 3-beta-HSD 1. In cattle, progesterone is involved in the metabolic pathway called the steroidogenesis pathway. Progesterone is a potentially toxic compound. |
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| Structure | |
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| Synonyms | | Value | Source |
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| (S)-4-Pregnene-3,20-dione | ChEBI | | (S)-Pregn-4-en-3,20-dione | ChEBI | | (S)-Progesterone | ChEBI | | 17alpha-Progesterone | ChEBI | | 4-Pregnene-3,20-dione | ChEBI | | Agolutin | ChEBI | | Akrolutin | ChEBI | | Corpus luteum hormone | ChEBI | | Crinone | ChEBI | | Delta(4)-Pregnene-3,20-dione | ChEBI | | Gelbkoerperhormon | ChEBI | | Luteohormone | ChEBI | | Progesteron | ChEBI | | Prometrium | Kegg | | 17a-Progesterone | Generator | | 17Α-progesterone | Generator | | Δ(4)-pregnene-3,20-dione | Generator | | 3,20-Pregnene-4 | HMDB | | 4-Pregnen-3,20-dione | HMDB | | beta-Progesterone | HMDB | | Bio-luton | HMDB | | CIDR | HMDB | | Colprosterone | HMDB | | Corlutin | HMDB | | Corlutina | HMDB | | Corluvite | HMDB | | Corporin | HMDB | | Crinone progesterone gel | HMDB | | Curretab | HMDB | | Cyclogest | HMDB | | Cyclogesterin | HMDB | | D4-Pregnene-3,20-dione | HMDB | | Delalutin | HMDB | | Duraprogen | HMDB | | Estima | HMDB | | Flavolutan | HMDB | | Fologenon | HMDB | | Gesterol | HMDB | | Gesterol 100 | HMDB | | Gesterol 50 | HMDB | | Gestiron | HMDB | | Gestone | HMDB | | Gestormone | HMDB | | Gestron | HMDB | | Glanducorpin | HMDB | | Gynlutin | HMDB | | Gynoluton | HMDB | | Gynolutone | HMDB | | Hormoflaveine | HMDB | | Hormoluton | HMDB | | Hydroxyprogesterone caproate | HMDB | | Hydroxyprogesterone caproic acid | HMDB | | Lingusorbs | HMDB | | Lipo-lutin | HMDB | | Lucorteum | HMDB | | Lucorteum sol | HMDB | | Lugesteron | HMDB | | Luteal hormone | HMDB | | Luteocrin normale | HMDB | | Luteodyn | HMDB | | Luteogan | HMDB | | Luteol | HMDB | | Luteopur | HMDB | | Luteosan | HMDB | | Luteostab | HMDB | | Luteovis | HMDB | | Luteum | HMDB | | Lutex | HMDB | | Lutidon | HMDB | | Lutociclina | HMDB | | Lutocuclin m | HMDB | | Lutocyclin | HMDB | | Lutocyclin m | HMDB | | Lutocylin | HMDB | | Lutocylol | HMDB | | Lutoform | HMDB | | Lutogyl | HMDB | | Lutren | HMDB | | Lutromone | HMDB | | Membrettes | HMDB | | Methylpregnone | HMDB | | MPA | HMDB | | Nalutron | HMDB | | Percutacrine | HMDB | | Percutacrine luteinique | HMDB | | Piaponon | HMDB | | Pranone | HMDB | | Pregn-4-en-3,20-dione | HMDB | | Pregn-4-ene-3,20-dione | HMDB | | Pregnene-3,20-dione | HMDB | | Pregnenedione | HMDB | | Primolut | HMDB | | Prochieve | HMDB | | Progeffik | HMDB | | Progekan | HMDB | | Progestan | HMDB | | Progestasert | HMDB | | Progesterol | HMDB | | Progesteronum | HMDB | | Progestin | HMDB | | Progestogel | HMDB | | Progestol | HMDB | | Progeston | HMDB | | Progestone | HMDB | | Progestosol | HMDB | | Progestron | HMDB | | Progestronol | HMDB | | Projestaject | HMDB | | Prolets | HMDB | | Prolidon | HMDB | | Prolutin | HMDB | | Proluton | HMDB | | Prolutone | HMDB | | Prontogest | HMDB | | Protormone | HMDB | | Syngesterone | HMDB | | Syngestrets | HMDB | | Synovex S | HMDB | | Syntolutan | HMDB | | Utrogest | HMDB | | Utrogestan | HMDB | | Vitarrine | HMDB | | Progesterone, (13 alpha,17 alpha)-(+-)-isomer | HMDB | | Progesterone, (17 alpha)-isomer | HMDB | | Progesterone, (9 beta,10 alpha)-isomer | HMDB |
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| Chemical Formula | C21H30O2 |
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| Average Molecular Weight | 314.4617 |
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| Monoisotopic Molecular Weight | 314.224580204 |
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| IUPAC Name | (1S,2R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one |
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| Traditional Name | (1S,2R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one |
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| CAS Registry Number | 57-83-0 |
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| SMILES | [H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C |
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| InChI Identifier | InChI=1S/C21H30O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,16-19H,4-11H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1 |
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| InChI Key | RJKFOVLPORLFTN-LEKSSAKUSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. |
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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 | Pregnane steroids |
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| Direct Parent | Gluco/mineralocorticoids, progestogins and derivatives |
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| Alternative Parents | |
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| Substituents | - Progestogin-skeleton
- 20-oxosteroid
- Oxosteroid
- 3-oxosteroid
- 3-oxo-delta-4-steroid
- Delta-4-steroid
- Cyclohexenone
- Cyclic ketone
- Ketone
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Status | Detected and Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | - Cell membrane
- Cytoplasm
- Endoplasmic reticulum
- Membrane
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 121 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 0.00881 mg/mL at 25 °C | YALKOWSKY,SH & DANNENFELSER,RM (1992) | | LogP | 3.87 | HANSCH,C ET AL. (1995) |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | |
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| GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0fbc-5910000000-422e38df6de7e8b0a4b7 | View in MoNA |
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| GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0fbc-5910000000-385f45345742235da8e0 | View in MoNA |
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| GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-024l-6923000000-639c7405f69825de7f90 | View in MoNA |
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| GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0229-2941000000-1e075d8489b79cf4e34a | View in MoNA |
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| GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0229-3963000000-f35e3d9faf6b2ee87465 | View in MoNA |
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| GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0fbc-5910000000-422e38df6de7e8b0a4b7 | View in MoNA |
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| GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0fbc-5910000000-385f45345742235da8e0 | View in MoNA |
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| GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0f6x-2910000000-1baafb91a3e0b988caa7 | View in MoNA |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-000g-1590000000-3ebb52b90c541e38c0b4 | View in MoNA |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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| LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-014i-1009000000-0f8b7c3e6c2265c3889f | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-052b-8900000000-0b0167121b798e7e7534 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-052b-9400000000-881510cbcecd9cb61f4f | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positive | splash10-024l-6923000000-639c7405f69825de7f90 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive | splash10-0229-2941000000-1e075d8489b79cf4e34a | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-004i-0950000000-ca28d8dfdf780c201716 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-000i-1900000000-857f6720dd17fb2547d1 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-004i-3930000000-fda87095285a83b85ad5 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-00kb-7955000000-a22f06eac940cd4f753d | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-014i-0139000000-6b47f75a44df3e20fa3b | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0aba-0950000000-b26d04d179294aa67cc7 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0aba-0920000000-d0a3365efe1f8a589564 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-05aj-0910000000-61d7a07e6be85600e1f1 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-014i-0009000000-67c6f0147801f0ece957 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-05mk-8956000000-aa5fe992c41261b62fbf | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-052b-6910000000-5e26497eb2d0150a30ac | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-0a4j-8900000000-7ca6fd15f0ccc18bfa31 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-052b-9700000000-523fe1ad11bfcbb46f85 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-054k-9400000000-e3d581bd8685e1d3f35d | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-0269000000-9aa25f8d44bc44ee4d4c | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-06dj-0491000000-c312ac322a549be24fac | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0pbc-2290000000-859101eb546be9ddc938 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0019000000-e021f799bd2d232a0592 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-0049000000-55066424591bf87a4a49 | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0002-1090000000-e9387b8ab692f5ef9083 | View in MoNA |
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| MS | Mass Spectrum (Electron Ionization) | splash10-006x-7931000000-f6ad83adccd7e016fa29 | View in MoNA |
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| 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental) | Not Available | View in JSpectraViewer |
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| 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental) | Not Available | View in JSpectraViewer |
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| 1D NMR | 13C NMR Spectrum (1D, 50.18 MHz, CDCl3, experimental) | Not Available | View in JSpectraViewer |
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| 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | Not Available | View in JSpectraViewer |
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