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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:04 UTC
HMDB IDHMDB0015668
Secondary Accession Numbers
  • HMDB15668
Metabolite Identification
Common NameGestodene
DescriptionGestodene is only found in individuals that have used or taken this drug.Gestodene is a progestogen hormonal contraceptive. Products containing gestoden include Meliane, which contains 20 mcg of ethinylestradiol and 75 mcg of gestodene; and Gynera, which contains 30 mcg of ethinylestradiol and 75 mcg of gestodene.
Structure
Data?1582753321
Synonyms
ValueSource
SH b 331HMDB
GestodenHMDB
13-Ethyl-17-hydroxy-18,19-dinor-17 alpha-pregna-4,15-dien-20-yn-3-oneHMDB
SH b 3331HMDB
17-alpha-Ethinyl-13-ethyl-17 beta-hydroxy-4,15-gonadien-3-oneHMDB
Gestodene, ((17alpha)-(+-))-isomerHMDB
Chemical FormulaC21H26O2
Average Molecular Weight310.4299
Monoisotopic Molecular Weight310.193280076
IUPAC Name(1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-6,12-dien-5-one
Traditional Namegestodene
CAS Registry Number60282-87-3
SMILES
CC[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@H]34)[C@@H]1C=C[C@@]2(O)C#C
InChI Identifier
InChI=1S/C21H26O2/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/h2,10,12-13,16-19,23H,3,5-9,11H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1
InChI KeySIGSPDASOTUPFS-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-oxosteroid
  • Hydroxysteroid
  • Oxosteroid
  • 17-hydroxysteroid
  • Cyclohexenone
  • Ynone
  • Tertiary alcohol
  • Ketone
  • Cyclic ketone
  • Acetylide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point197.9 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0058 g/LALOGPS
logP3.15ALOGPS
logP3.46ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)17.08ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity92.99 m³·mol⁻¹ChemAxon
Polarizability35.94 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]+174.21631661259
DarkChem[M-H]-175.42631661259
DeepCCS[M-2H]-219.33930932474
DeepCCS[M+Na]+195.42130932474
AllCCS[M+H]+179.032859911
AllCCS[M+H-H2O]+175.832859911
AllCCS[M+NH4]+181.932859911
AllCCS[M+Na]+182.732859911
AllCCS[M-H]-184.432859911
AllCCS[M+Na-2H]-184.432859911
AllCCS[M+HCOO]-184.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
GestodeneCC[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@H]34)[C@@H]1C=C[C@@]2(O)C#C3713.8Standard polar33892256
GestodeneCC[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@H]34)[C@@H]1C=C[C@@]2(O)C#C2696.8Standard non polar33892256
GestodeneCC[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@H]34)[C@@H]1C=C[C@@]2(O)C#C2681.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Gestodene,1TMS,isomer #1C#C[C@]1(O[Si](C)(C)C)C=C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21CC2851.0Semi standard non polar33892256
Gestodene,1TMS,isomer #2C#C[C@]1(O)C=C[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC2696.4Semi standard non polar33892256
Gestodene,2TMS,isomer #1C#C[C@]1(O[Si](C)(C)C)C=C[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC2786.6Semi standard non polar33892256
Gestodene,2TMS,isomer #1C#C[C@]1(O[Si](C)(C)C)C=C[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC2815.4Standard non polar33892256
Gestodene,2TMS,isomer #1C#C[C@]1(O[Si](C)(C)C)C=C[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC3290.1Standard polar33892256
Gestodene,1TBDMS,isomer #1C#C[C@]1(O[Si](C)(C)C(C)(C)C)C=C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21CC3106.6Semi standard non polar33892256
Gestodene,1TBDMS,isomer #2C#C[C@]1(O)C=C[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC2971.5Semi standard non polar33892256
Gestodene,2TBDMS,isomer #1C#C[C@]1(O[Si](C)(C)C(C)(C)C)C=C[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC3322.4Semi standard non polar33892256
Gestodene,2TBDMS,isomer #1C#C[C@]1(O[Si](C)(C)C(C)(C)C)C=C[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC3286.5Standard non polar33892256
Gestodene,2TBDMS,isomer #1C#C[C@]1(O[Si](C)(C)C(C)(C)C)C=C[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC3489.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Gestodene GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-0590000000-0ae848be3d8a8c4e03902017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gestodene GC-MS (1 TMS) - 70eV, Positivesplash10-0gb9-1339000000-eec167d7cdc5857052842017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gestodene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gestodene 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 - Gestodene 40V, Positive-QTOFsplash10-0fbc-0910000000-f78be4e55be72987c86a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gestodene 30V, Positive-QTOFsplash10-0kaj-0920000000-8e7c943a5ade2dcf23612021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gestodene 10V, Positive-QTOFsplash10-03di-0009000000-e311e146b48c013646982021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gestodene 20V, Positive-QTOFsplash10-03di-0759000000-639b7bc095ad306f7cf32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gestodene 40V, Positive-QTOFsplash10-0fbc-0910000000-0bd07f5d796b4f8935492021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gestodene 50V, Positive-QTOFsplash10-00ou-0900000000-6d2a0be9e20d6f98f9ec2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gestodene 30V, Positive-QTOFsplash10-0kaj-0920000000-e98c1051a49916cdccc52021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gestodene 10V, Positive-QTOFsplash10-03di-0179000000-959f6c3a1ad2ee1501822016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gestodene 20V, Positive-QTOFsplash10-01px-0191000000-b1ab41a59d167d8daa5b2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gestodene 40V, Positive-QTOFsplash10-0uec-4690000000-c95a90b1a2652620de842016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gestodene 10V, Negative-QTOFsplash10-0a4i-0019000000-a6c0ac024a65d327f7c42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gestodene 20V, Negative-QTOFsplash10-0a4i-0059000000-34da217065f0fd643dc62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gestodene 40V, Negative-QTOFsplash10-0kcu-0090000000-070c5a39f651450e461a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gestodene 10V, Positive-QTOFsplash10-0006-0090000000-af63cd8f347d3cf069362021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gestodene 20V, Positive-QTOFsplash10-02tc-0391000000-75cb366ab4597609b5e82021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gestodene 40V, Positive-QTOFsplash10-03xs-1890000000-a1e1ca10a4691110fb1b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gestodene 10V, Negative-QTOFsplash10-0a4i-0009000000-d834b990dbff0e00d2662021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gestodene 20V, Negative-QTOFsplash10-0a4i-0019000000-c052dcefafdd437fec672021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gestodene 40V, Negative-QTOFsplash10-0a5c-1291000000-0df40a773eac7c585fe72021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 DB06730 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06730 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06730
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2298532
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGestodene
METLIN IDNot Available
PubChem Compound3033968
PDB IDNot Available
ChEBI ID785428
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular weight:
57108.065
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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular weight:
57525.03