Norgestimate (CED0008191)

Record Information
Version1.0
Creation Date2016-05-22 06:02:46 UTC
Update Date2026-08-22 01:41:52 UTC
Accession NumberCHEM019356
Identification
Common NameNorgestimate
ClassSmall Molecule
Description
Norgestimate is an organic compound with the formula C23H31NO3 and an average molecular weight of 369.50 g/mol. Norgestimate belongs to the steroid esters, a subclass of steroids and steroid derivatives within the organic compounds. This compound is found in or released from healthcare, pharmaceuticals, and veterinary products, specifically progestogens and estrogens in combination and hormonal contraceptives for systemic use. The recorded route of exposure for this substance is oral. Regarding its biological activity, norgestimate acts as an agonist or partial agonist of three protein targets: the progesterone receptor (PGR), the estrogen receptor (ESR1), and the androgen receptor (AR).
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one oxime acetate (ester)ChEBI
(17alpha)-17-(Acetyloxy)-13-ethyl-18,19-dinorpregn-4-en-20-yn-3-one 3-oximeChEBI
D-13beta-Ethyl-17alpha-ethynyl-17beta-acetoxygon-4-en-3-one oximeChEBI
Dexnorgestrel acetimeChEBI
NorgestimatoChEBI
NorgestimatumChEBI
(+)-13-Ethyl-17-hydroxy-18,19-dinor-17a-pregn-4-en-20-yn-3-one oxime acetate (ester)Generator
(+)-13-Ethyl-17-hydroxy-18,19-dinor-17a-pregn-4-en-20-yn-3-one oxime acetic acid (ester)Generator
(+)-13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one oxime acetic acid (ester)Generator
(+)-13-Ethyl-17-hydroxy-18,19-dinor-17α-pregn-4-en-20-yn-3-one oxime acetate (ester)Generator
(+)-13-Ethyl-17-hydroxy-18,19-dinor-17α-pregn-4-en-20-yn-3-one oxime acetic acid (ester)Generator
(17a)-17-(Acetyloxy)-13-ethyl-18,19-dinorpregn-4-en-20-yn-3-one 3-oximeGenerator
(17Α)-17-(acetyloxy)-13-ethyl-18,19-dinorpregn-4-en-20-yn-3-one 3-oximeGenerator
D-13b-Ethyl-17a-ethynyl-17b-acetoxygon-4-en-3-one oximeGenerator
D-13Β-ethyl-17α-ethynyl-17β-acetoxygon-4-en-3-one oximeGenerator
Norgestimic acidGenerator
Norgestrel oxime acetateHMDB
Chemical FormulaC23H31NO3
Average Molecular Mass369.497 g/mol
Monoisotopic Mass369.230 g/mol
CAS Registry Number35189-28-7
IUPAC Name(1S,2R,5E,10R,11S,14R,15S)-15-ethyl-14-ethynyl-5-(hydroxyimino)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl acetate
Traditional Namenorgestimate
SMILES[H][C@@]12CC[C@@](OC(C)=O)(C#C)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CC\C(C=C3CC[C@@]21[H])=N/O
InChI IdentifierInChI=1S/C23H31NO3/c1-4-22-12-10-19-18-9-7-17(24-26)14-16(18)6-8-20(19)21(22)11-13-23(22,5-2)27-15(3)25/h2,14,18-21,26H,4,6-13H2,1,3H3/b24-17+/t18-,19+,20+,21-,22-,23-/m0/s1
InChI KeyKIQQMECNKUGGKA-NMYWJIRASA-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
  • Ketoxime
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Oxime
  • Acetylide
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0053 g/LALOGPS
logP3.8ALOGPS
logP4.11ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)11.47ChemAxon
pKa (Strongest Basic)3.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area58.89 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity105 m³·mol⁻¹ChemAxon
Polarizability42.82 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-2698000000-7e02d6124cbf30e8be87Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0009000000-b5b2b147e5ce033804a6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0009000000-1bb2450b5dc4140f5e93Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0209000000-c0873e43f4129a09814dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0922000000-9b40bb72db6c044b370cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0922000000-59c3543a046f1a654729Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05i3-0910000000-6a2449a24f6efdf10513Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0009000000-cda4a2de67f83fe17601Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0129000000-e3b5fba490277d952c9eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-6491000000-51d7c89ce72eb09d3993Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-016r-1009000000-2b5a8cbd62430bb58addNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05r0-2009000000-05bf9254a578ac3a1a11Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-4029000000-76a6829838c24ac7bd2cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0019000000-ffdfef9c7bc973ccee83Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0293000000-fcd7c087298d41406df8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01qa-0930000000-01441e5a4930cf72a343Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-3009000000-8b4cc4a89faf8b738f0eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0049000000-27e791a48fed12ec9d0aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zfs-2049000000-4e6f026ed6781f5b8b3bNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2124.0Log mg/kg[1200:3800]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
317Hormonal contraceptives for systemic useHealthcare, pharmaceuticals & veterinary productsNot Available
322Progestogens and estrogens in combinationHealthcare, pharmaceuticals & veterinary productsNot Available
Pathways
1 pathway
Norgestimate Drug Metabolism Action Pathway
Norgestimate Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureAndrogen receptorP15207Rattus norvegicusPredicted (SEA)8.01847
Click to view 3D structureProgesterone receptorQ690N0Bos taurusPredicted (SEA)3.65891
Sex hormone-binding globulin structureClick to view 3D structureSex hormone-binding globulinP04278HumansPredicted (SEA)12.2223
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)161.459
Glucocorticoid receptor structureClick to view 3D structureGlucocorticoid receptorP04150HumansPredicted (SEA)33.7866
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansPredicted (SEA)130.553
Progesterone receptor structureClick to view 3D structureProgesterone receptorP06401HumansPredicted (SEA)95.5988
Corticosteroid-binding globulin structureClick to view 3D structureCorticosteroid-binding globulinP08185HumansPredicted (SEA)27.2472
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)1804.93
Androgen receptor structureClick to view 3D structureAndrogen receptorP10275HumansPredicted (SEA)554.131
Mineralocorticoid receptor structureClick to view 3D structureMineralocorticoid receptorP08235HumansPredicted (SEA)239.464
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)5350.73
Steroid 17-alpha-hydroxylase/17,20 lyase structureClick to view 3D structureSteroid 17-alpha-hydroxylase/17,20 lyaseP05093HumansPredicted (SEA)184.97
Amine oxidase [flavin-containing] A structureClick to view 3D structureAmine oxidase [flavin-containing] AP21397HumansPredicted (SEA)1763.6
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)817.339
Click to view 3D structureAndrogen receptorP19091Mus musculusPredicted (SEA)67.3396
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)6715.74
Click to view 3D structure3-oxo-5-alpha-steroid 4-dehydrogenase 1P18405HumansPredicted (SEA)26.9358
Estrogen receptor beta structureClick to view 3D structureEstrogen receptor betaQ92731HumansPredicted (SEA)2389.66
Click to view 3D structureGlucocorticoid receptorP06536Rattus norvegicusPredicted (SEA)69.4415
3-oxo-5-alpha-steroid 4-dehydrogenase 2 structureClick to view 3D structure3-oxo-5-alpha-steroid 4-dehydrogenase 2P31213HumansPredicted (SEA)56.4407
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)5543.64
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansPredicted (SEA)4921.24
Muscarinic acetylcholine receptor M2 structureClick to view 3D structureMuscarinic acetylcholine receptor M2P08172HumansPredicted (SEA)5291.26
Click to view 3D structureGlucocorticoid receptorQ9N1U3Sus scrofaPredicted (SEA)8.17417
Concentrations
Not Available
External Links
DrugBank IDDB00957
HMDB IDHMDB0015092
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNorgestimate
Chemspider ID5022837
ChEBI ID50815
PubChem Compound ID6540478
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
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.
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.
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.
5. The lipid handbook with CD-ROM