Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:39 UTC
HMDB IDHMDB0014511
Secondary Accession Numbers
  • HMDB14511
Metabolite Identification
Common NameLevonorgestrel
DescriptionLevonorgestrel, also known as microlut or norplant, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, levonorgestrel is considered to be a steroid lipid molecule. Levonorgestrel is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Levonorgestrel is a potentially toxic compound.
Structure
Data?1582753187
Synonyms
ValueSource
(-)-13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-oneChEBI
13-beta-Ethyl-17alpha-ethynyl-17beta-hydroxygon-4-en-3-oneChEBI
13-Ethyl-17-alpha-ethynyl-17-beta-hydroxy-4-gonen-3-oneChEBI
13-Ethyl-17-alpha-ethynylgon-4-en-17-beta-ol-3-oneChEBI
17-alpha-Ethinyl-13-beta-ethyl-17-beta-hydroxy-4-estren-3-oneChEBI
17-alpha-Ethynyl-13-ethyl-19-nortestosteroneChEBI
17-Ethynyl-18-methyl-19-nortestosteroneChEBI
17alpha-Ethynyl-13beta-ethyl-3-oxo-4-estren-17beta-olChEBI
17alpha-Ethynyl-17-hydroxy-18-methylestr-4-en-3-oneChEBI
17alpha-Ethynyl-18-homo-19-nortestosteroneChEBI
18-Methyl-17-alpha-ethynyl-19-nortestosteroneChEBI
18-MethylnorethisteroneChEBI
D(-)-NorgestrelChEBI
JadelleChEBI
LevonelleChEBI
LevonorgestrelumChEBI
LevonovaChEBI
MicrolutChEBI
MicrolutonChEBI
MicrovalChEBI
MirenaChEBI
NorLevoChEBI
Plan bChEBI
PostinorChEBI
(+-)-NorgestrelKegg
OvretteKegg
(-)-13-Ethyl-17-hydroxy-18,19-dinor-17a-pregn-4-en-20-yn-3-oneGenerator
(-)-13-Ethyl-17-hydroxy-18,19-dinor-17α-pregn-4-en-20-yn-3-oneGenerator
13-b-Ethyl-17a-ethynyl-17b-hydroxygon-4-en-3-oneGenerator
13-Β-ethyl-17α-ethynyl-17β-hydroxygon-4-en-3-oneGenerator
13-Ethyl-17-a-ethynyl-17-b-hydroxy-4-gonen-3-oneGenerator
13-Ethyl-17-α-ethynyl-17-β-hydroxy-4-gonen-3-oneGenerator
13-Ethyl-17-a-ethynylgon-4-en-17-b-ol-3-oneGenerator
13-Ethyl-17-α-ethynylgon-4-en-17-β-ol-3-oneGenerator
17-a-Ethinyl-13-b-ethyl-17-b-hydroxy-4-estren-3-oneGenerator
17-Α-ethinyl-13-β-ethyl-17-β-hydroxy-4-estren-3-oneGenerator
17-a-Ethynyl-13-ethyl-19-nortestosteroneGenerator
17-Α-ethynyl-13-ethyl-19-nortestosteroneGenerator
17a-Ethynyl-13b-ethyl-3-oxo-4-estren-17b-olGenerator
17Α-ethynyl-13β-ethyl-3-oxo-4-estren-17β-olGenerator
17a-Ethynyl-17-hydroxy-18-methylestr-4-en-3-oneGenerator
17Α-ethynyl-17-hydroxy-18-methylestr-4-en-3-oneGenerator
17a-Ethynyl-18-homo-19-nortestosteroneGenerator
17Α-ethynyl-18-homo-19-nortestosteroneGenerator
18-Methyl-17-a-ethynyl-19-nortestosteroneGenerator
18-Methyl-17-α-ethynyl-19-nortestosteroneGenerator
Levonorgestrel alcala brandHMDB
Levonorgestrel hexal brandHMDB
NorplantHMDB
Paladin brand OF levonorgestrelHMDB
VikelaHMDB
Wyeth brand OF levonorgestrelHMDB
DuofemHMDB
L-NorgestrelHMDB
Aventis pharma brand OF levonorgestrelHMDB
Berlex brand OF levonorgestrelHMDB
HRA brand 1 OF levonorgestrelHMDB
Hexal brand OF levonorgestrelHMDB
Levonorgestrel paladin brandHMDB
Levonorgestrel wyeth brandHMDB
Norplant 2HMDB
Alcala brand OF levonorgestrelHMDB
CapronorHMDB
CerazetHMDB
D-NorgestrelHMDB
HRA brand 2 OF levonorgestrelHMDB
Norplant-2HMDB
Schering brand 3 OF levonorgestrelHMDB
L NorgestrelHMDB
D NorgestrelHMDB
Levonorgestrel berlex brandHMDB
NorgestonHMDB
Norplant2HMDB
Schering brand 1 OF levonorgestrelHMDB
Schering brand 2 OF levonorgestrelHMDB
Women's capital brand OF levonorgestrelHMDB
LevonorgestrelMeSH
Chemical FormulaC21H28O2
Average Molecular Weight312.4458
Monoisotopic Molecular Weight312.20893014
IUPAC Name(1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
Traditional Name(1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
CAS Registry Number797-63-7
SMILES
[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]
InChI Identifier
InChI=1S/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1
InChI KeyWWYNJERNGUHSAO-XUDSTZEESA-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrogens and derivatives
Alternative Parents
Substituents
  • Estrogen-skeleton
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • 17-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Ynone
  • Cyclic alcohol
  • Tertiary alcohol
  • Cyclic ketone
  • Ketone
  • Acetylide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • terminal acetylenic compound (CHEBI:6443 )
  • 3-oxo Delta(4)-steroid (CHEBI:6443 )
  • 17beta-hydroxy steroid (CHEBI:6443 )
  • Pregnane and derivatives [Fig] (C08153 )
  • C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C08153 )
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030119 )
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point240 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0058 g/LNot Available
LogP3.8Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available178.634http://allccs.zhulab.cn/database/detail?ID=AllCCS00001174
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0058 g/LALOGPS
logP3.25ALOGPS
logP3.66ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)17.91ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity92.03 m³·mol⁻¹ChemAxon
Polarizability36.75 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+175.54631661259
DarkChem[M-H]-175.42331661259
DeepCCS[M-2H]-209.67730932474
DeepCCS[M+Na]+183.90530932474
AllCCS[M+H]+180.032859911
AllCCS[M+H-H2O]+177.132859911
AllCCS[M+NH4]+182.732859911
AllCCS[M+Na]+183.532859911
AllCCS[M-H]-185.132859911
AllCCS[M+Na-2H]-185.332859911
AllCCS[M+HCOO]-185.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Levonorgestrel[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]3776.6Standard polar33892256
Levonorgestrel[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]2716.4Standard non polar33892256
Levonorgestrel[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]2765.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Levonorgestrel,1TMS,isomer #1C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21CC2867.1Semi standard non polar33892256
Levonorgestrel,1TMS,isomer #2C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC2760.1Semi standard non polar33892256
Levonorgestrel,2TMS,isomer #1C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC2837.5Semi standard non polar33892256
Levonorgestrel,2TMS,isomer #1C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC2914.3Standard non polar33892256
Levonorgestrel,2TMS,isomer #1C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC3258.3Standard polar33892256
Levonorgestrel,1TBDMS,isomer #1C#C[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21CC3128.6Semi standard non polar33892256
Levonorgestrel,1TBDMS,isomer #2C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC3025.5Semi standard non polar33892256
Levonorgestrel,2TBDMS,isomer #1C#C[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC3345.5Semi standard non polar33892256
Levonorgestrel,2TBDMS,isomer #1C#C[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC3383.2Standard non polar33892256
Levonorgestrel,2TBDMS,isomer #1C#C[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC3436.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Levonorgestrel GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-0490000000-497c4ebd506c0b9c8ec32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Levonorgestrel GC-MS (1 TMS) - 70eV, Positivesplash10-0a4l-1259000000-2a7acf9f8fd01faadc862017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Levonorgestrel GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Levonorgestrel LC-ESI-qTof , Positive-QTOFsplash10-066r-0931000000-4a863e895a5edd6cebeb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levonorgestrel , positive-QTOFsplash10-03di-0439000000-bcbc7c657a115dced40a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levonorgestrel , positive-QTOFsplash10-0a5a-3920000000-edbd3785e7d20d9e81be2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levonorgestrel , positive-QTOFsplash10-0a4i-2920000000-a08b14b6d762cf4c42b12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levonorgestrel 45V, Negative-QTOFsplash10-0002-0900000000-ccbe00eb6d33f44bf13e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levonorgestrel 30V, Negative-QTOFsplash10-03dj-0809000000-3b4f03aa1582c55a88a42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levonorgestrel 45V, Positive-QTOFsplash10-0a59-2910000000-2e210ea979850c3d19ac2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levonorgestrel 90V, Negative-QTOFsplash10-0002-0900000000-87a5333787ffe2461b522021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levonorgestrel 30V, Positive-QTOFsplash10-03dj-1943000000-e4eeb86036aa8456827f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levonorgestrel 35V, Positive-QTOFsplash10-06r2-0932000000-542d94c4f65730336be82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levonorgestrel 75V, Negative-QTOFsplash10-0002-0900000000-d9c9cc75f7d6522925902021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levonorgestrel 60V, Negative-QTOFsplash10-0002-0900000000-a5a5bd10465f22e61a652021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levonorgestrel 15V, Positive-QTOFsplash10-03di-0009000000-0d184562b2bcf62fab5c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levonorgestrel 75V, Positive-QTOFsplash10-055f-7900000000-2c2242a1883d4b23fb142021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levonorgestrel 60V, Positive-QTOFsplash10-0a5c-4900000000-64d2115a1e9554b157802021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levonorgestrel 90V, Positive-QTOFsplash10-05po-9700000000-f172af0f505e7230dfcc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levonorgestrel 15V, Negative-QTOFsplash10-03di-0009000000-73765d8e0531c2c942512021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levonorgestrel 10V, Positive-QTOFsplash10-03di-0179000000-09f92950350c9411f4dc2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levonorgestrel 20V, Positive-QTOFsplash10-0btj-0191000000-7bd7256abde150b22d9f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levonorgestrel 40V, Positive-QTOFsplash10-0f76-2390000000-84a923da67ade6ef90a82016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levonorgestrel 10V, Negative-QTOFsplash10-03di-0019000000-3f0cb0e2e76214741c6f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levonorgestrel 20V, Negative-QTOFsplash10-03di-0059000000-f6e5c83ac4c0da584cb22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levonorgestrel 40V, Negative-QTOFsplash10-053v-0090000000-6bb0ea8f0fc81b4c6fe22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levonorgestrel 10V, Negative-QTOFsplash10-03di-0009000000-152b659b4891e36b54f32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levonorgestrel 20V, Negative-QTOFsplash10-03di-0019000000-51b6ec5de157050ca35e2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00367 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00367 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00367
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID12560
KEGG Compound IDC08153
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLevonorgestrel
METLIN IDNot Available
PubChem Compound13109
PDB IDNot Available
ChEBI ID6443
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sitruk-Ware R: New progestagens for contraceptive use. Hum Reprod Update. 2006 Mar-Apr;12(2):169-78. Epub 2005 Nov 16. [PubMed:16291771 ]
  2. Edgren RA, Stanczyk FZ: Nomenclature of the gonane progestins. Contraception. 1999 Dec;60(6):313. [PubMed:10715364 ]
  3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  4. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  5. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  6. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  7. (). FDA label.. .
  8. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in 3-oxo-5-alpha-steroid 4-dehydrogenase activity
Specific function:
Converts testosterone into 5-alpha-dihydrotestosterone and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and androgen physiology.
Gene Name:
SRD5A1
Uniprot ID:
P18405
Molecular weight:
29458.18
References
  1. Hammond GL, Rabe T, Wagner JD: Preclinical profiles of progestins used in formulations of oral contraceptives and hormone replacement therapy. Am J Obstet Gynecol. 2001 Aug;185(2 Suppl):S24-31. [PubMed:11521119 ]
  2. Rabe T, Kowald A, Ortmann J, Rehberger-Schneider S: Inhibition of skin 5 alpha-reductase by oral contraceptive progestins in vitro. Gynecol Endocrinol. 2000 Aug;14(4):223-30. [PubMed:11075290 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. 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 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
  1. 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
  1. Shields-Botella J, Duc I, Duranti E, Puccio F, Bonnet P, Delansorne R, Paris J: An overview of nomegestrol acetate selective receptor binding and lack of estrogenic action on hormone-dependent cancer cells. J Steroid Biochem Mol Biol. 2003 Nov;87(2-3):111-22. [PubMed:14672731 ]
  2. Freyberger A, Witters H, Weimer M, Lofink W, Berckmans P, Ahr HJ: Screening for (anti)androgenic properties using a standard operation protocol based on the human stably transfected androgen sensitive PALM cell line. First steps towards validation. Reprod Toxicol. 2010 Aug;30(1):9-17. doi: 10.1016/j.reprotox.2009.10.002. Epub 2009 Oct 27. [PubMed:19836445 ]
  3. Freyberger A, Weimer M, Tran HS, Ahr HJ: Assessment of a recombinant androgen receptor binding assay: initial steps towards validation. Reprod Toxicol. 2010 Aug;30(1):2-8. doi: 10.1016/j.reprotox.2009.10.001. Epub 2009 Oct 13. [PubMed:19833195 ]
  4. Kloosterboer HJ, Vonk-Noordegraaf CA, Turpijn EW: Selectivity in progesterone and androgen receptor binding of progestagens used in oral contraceptives. Contraception. 1988 Sep;38(3):325-32. [PubMed:3139361 ]
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Isoform A is inactive in stimulating c-Src/MAPK signaling on hormone stimulation
Gene Name:
PGR
Uniprot ID:
P06401
Molecular weight:
98980.0
References
  1. Maruo T, Ohara N, Matsuo H, Xu Q, Chen W, Sitruk-Ware R, Johansson ED: Effects of levonorgestrel-releasing IUS and progesterone receptor modulator PRM CDB-2914 on uterine leiomyomas. Contraception. 2007 Jun;75(6 Suppl):S99-103. Epub 2007 Mar 21. [PubMed:17531625 ]
  2. Mirkin S, Wong BC, Archer DF: Effect of 17 beta-estradiol, progesterone, synthetic progestins, tibolone, and tibolone metabolites on vascular endothelial growth factor mRNA in breast cancer cells. Fertil Steril. 2005 Aug;84(2):485-91. [PubMed:16084894 ]
  3. Hompes PG, Mijatovic V: Endometriosis: the way forward. Gynecol Endocrinol. 2007 Jan;23(1):5-12. [PubMed:17484506 ]
  4. Creinin MD, Schlaff W, Archer DF, Wan L, Frezieres R, Thomas M, Rosenberg M, Higgins J: Progesterone receptor modulator for emergency contraception: a randomized controlled trial. Obstet Gynecol. 2006 Nov;108(5):1089-97. [PubMed:17077229 ]
  5. Bray JD, Jelinsky S, Ghatge R, Bray JA, Tunkey C, Saraf K, Jacobsen BM, Richer JK, Brown EL, Winneker RC, Horwitz KB, Lyttle CR: Quantitative analysis of gene regulation by seven clinically relevant progestins suggests a highly similar mechanism of action through progesterone receptors in T47D breast cancer cells. J Steroid Biochem Mol Biol. 2005 Dec;97(4):328-41. Epub 2005 Sep 12. [PubMed:16157482 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Can activate the transcriptional activity of TFF1
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular weight:
66215.4
References
  1. Vereide AB, Kaino T, Sager G, Arnes M, Orbo A: Effect of levonorgestrel IUD and oral medroxyprogesterone acetate on glandular and stromal progesterone receptors (PRA and PRB), and estrogen receptors (ER-alpha and ER-beta) in human endometrial hyperplasia. Gynecol Oncol. 2006 May;101(2):214-23. Epub 2005 Dec 1. [PubMed:16325240 ]
  2. Mirkin S, Wong BC, Archer DF: Effect of 17 beta-estradiol, progesterone, synthetic progestins, tibolone, and tibolone metabolites on vascular endothelial growth factor mRNA in breast cancer cells. Fertil Steril. 2005 Aug;84(2):485-91. [PubMed:16084894 ]
  3. Abdel-Aleem H, Shaaban OM, Amin AF, Abdel-Aleem AM: Tamoxifen treatment of bleeding irregularities associated with Norplant use. Contraception. 2005 Dec;72(6):432-7. Epub 2005 Aug 9. [PubMed:16307966 ]
  4. Sun D, Yan C, Jacobson A, Jiang H, Carroll MA, Huang A: Contribution of epoxyeicosatrienoic acids to flow-induced dilation in arteries of male ERalpha knockout mice: role of aromatase. Am J Physiol Regul Integr Comp Physiol. 2007 Sep;293(3):R1239-46. Epub 2007 Jul 18. [PubMed:17634204 ]
  5. Vijayanathan V, Venkiteswaran S, Nair SK, Verma A, Thomas TJ, Zhu BT, Thomas T: Physiologic levels of 2-methoxyestradiol interfere with nongenomic signaling of 17beta-estradiol in human breast cancer cells. Clin Cancer Res. 2006 Apr 1;12(7 Pt 1):2038-48. [PubMed:16609013 ]