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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:42 UTC
HMDB IDHMDB0014961
Secondary Accession Numbers
  • HMDB14961
Metabolite Identification
Common NameEthynodiol Diacetate
DescriptionEthynodiol Diacetate is only found in individuals that have used or taken this drug. It is a synthetic progestational hormone used alone or in combination with estrogens as an oral contraceptive. [PubChem]Binds to the progesterone and estrogen receptors. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progestins like Ethynodiol Diacetate will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH (luteinizing hormone) surge.
Structure
Data?1582753242
Synonyms
ValueSource
17alpha-Ethynyl-19-norandrost-4-ene-3beta,17-beta-diol diacetateChEBI
17alpha-Ethynyl-3,17-dihydroxy-4-estrene diacetateChEBI
17alpha-Ethynyl-4-estrene-3beta,17beta-diol diacetateChEBI
17alpha-Ethynylestr-4-ene-3beta,17beta-diol acetateChEBI
19-Nor-17alpha-pregn-4-en-20-yne-3beta,17-diol diacetateChEBI
3beta, 17beta-Diacetoxy-17alpha-ethynyl-4-oestreneChEBI
3beta,17beta-Diacetoxy-19-nor-17alpha-pregn-4-en-20-yneChEBI
17a-Ethynyl-19-norandrost-4-ene-3b,17-b-diol diacetateGenerator
17a-Ethynyl-19-norandrost-4-ene-3b,17-b-diol diacetic acidGenerator
17alpha-Ethynyl-19-norandrost-4-ene-3beta,17-beta-diol diacetic acidGenerator
17Α-ethynyl-19-norandrost-4-ene-3β,17-β-diol diacetateGenerator
17Α-ethynyl-19-norandrost-4-ene-3β,17-β-diol diacetic acidGenerator
17a-Ethynyl-3,17-dihydroxy-4-estrene diacetateGenerator
17a-Ethynyl-3,17-dihydroxy-4-estrene diacetic acidGenerator
17alpha-Ethynyl-3,17-dihydroxy-4-estrene diacetic acidGenerator
17Α-ethynyl-3,17-dihydroxy-4-estrene diacetateGenerator
17Α-ethynyl-3,17-dihydroxy-4-estrene diacetic acidGenerator
17a-Ethynyl-4-estrene-3b,17b-diol diacetateGenerator
17a-Ethynyl-4-estrene-3b,17b-diol diacetic acidGenerator
17alpha-Ethynyl-4-estrene-3beta,17beta-diol diacetic acidGenerator
17Α-ethynyl-4-estrene-3β,17β-diol diacetateGenerator
17Α-ethynyl-4-estrene-3β,17β-diol diacetic acidGenerator
17a-Ethynylestr-4-ene-3b,17b-diol acetateGenerator
17a-Ethynylestr-4-ene-3b,17b-diol acetic acidGenerator
17alpha-Ethynylestr-4-ene-3beta,17beta-diol acetic acidGenerator
17Α-ethynylestr-4-ene-3β,17β-diol acetateGenerator
17Α-ethynylestr-4-ene-3β,17β-diol acetic acidGenerator
19-Nor-17a-pregn-4-en-20-yne-3b,17-diol diacetateGenerator
19-Nor-17a-pregn-4-en-20-yne-3b,17-diol diacetic acidGenerator
19-Nor-17alpha-pregn-4-en-20-yne-3beta,17-diol diacetic acidGenerator
19-Nor-17α-pregn-4-en-20-yne-3β,17-diol diacetateGenerator
19-Nor-17α-pregn-4-en-20-yne-3β,17-diol diacetic acidGenerator
3b, 17b-Diacetoxy-17a-ethynyl-4-oestreneGenerator
3Β, 17β-diacetoxy-17α-ethynyl-4-oestreneGenerator
3b,17b-Diacetoxy-19-nor-17a-pregn-4-en-20-yneGenerator
3Β,17β-diacetoxy-19-nor-17α-pregn-4-en-20-yneGenerator
Ethynodiol diacetic acidGenerator
Ethinodiol diacetateHMDB
EthynodiolHMDB
EtynodiolHMDB
Ethyndiol diacetateHMDB
Diacetate, ethyndiolHMDB
Ethynodiol diacetate, (17 alpha)-isomerHMDB
FemulenHMDB
ContinuinHMDB
(3 beta, 17 alpha)-19-Norpregn-4-en-20-yne-3,17 diol diacetateHMDB
Diacetate, ethynodiolHMDB
Chemical FormulaC24H32O4
Average Molecular Weight384.5085
Monoisotopic Molecular Weight384.230059512
IUPAC Name(1S,2R,5S,10R,11S,14R,15S)-5-(acetyloxy)-14-ethynyl-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl acetate
Traditional Nameethynodiol diacetate
CAS Registry Number297-76-7
SMILES
[H][C@@]12CC[C@@](OC(C)=O)(C#C)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CC[C@H](OC(C)=O)C=C3CC[C@@]21[H]
InChI Identifier
InChI=1S/C24H32O4/c1-5-24(28-16(3)26)13-11-22-21-8-6-17-14-18(27-15(2)25)7-9-19(17)20(21)10-12-23(22,24)4/h1,14,18-22H,6-13H2,2-4H3/t18-,19-,20+,21+,22-,23-,24-/m0/s1
InChI KeyONKUMRGIYFNPJW-KIEAKMPYSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid esters
Direct ParentSteroid esters
Alternative Parents
Substituents
  • Steroid ester
  • Estrane-skeleton
  • Delta-4-steroid
  • Ynone
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Acetylide
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • terminal acetylenic compound (CHEBI:31580 )
  • steroid ester (CHEBI:31580 )
  • C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C12724 )
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030124 )
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.004 g/LNot Available
LogP5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.004 g/LALOGPS
logP3.99ALOGPS
logP3.69ChemAxon
logS-5ALOGPS
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity106.62 m³·mol⁻¹ChemAxon
Polarizability44.11 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0100-1194000000-36378317102183460faeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002u-0019000000-a73cd21b30c9439d33beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-0079000000-136800a52b34f352d78eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00e9-0290000000-2ea658e56bd9ec1ef885Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000x-0009000000-85f53cde1cbdf66e3366Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000x-2029000000-0187f016d0d4a58f5182Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052e-7094000000-0495ab26817d2a5560a9Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00823 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00823 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00823
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8913
KEGG Compound IDC12724
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthynodiol_Diacetate
METLIN IDNot Available
PubChem Compound9270
PDB IDNot Available
ChEBI ID31580
Food Biomarker OntologyNot Available
VMH 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 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. Tamaya T, Nioka S, Furuta N, Shimura T, Takano N: Contribution of functional groups of 19-nor-progestogens to binding to progesterone and estradiol-17beta receptors in rabbit uterus. Endocrinology. 1977 Jun;100(6):1579-84. [PubMed:858280 ]
  2. Briggs MH: Contraceptive steroid binding to the human uterine progesterone-receptor. Curr Med Res Opin. 1975;3(2):95-8. [PubMed:166800 ]
  3. 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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Kappus H, Bolt HM, Remmer H: Affinity of ethynyl-estradiol and mestranol for the uterine estrogen receptor and for the microsomal mixed function oxidase of the liver. J Steroid Biochem. 1973 Mar;4(2):121-8. [PubMed:4123746 ]