Norgestimate (CHEM019356)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:02:46 UTC
Update Date2016-11-09 01:15:58 UTC
Accession NumberCHEM019356
Identification
Common NameNorgestimate
ClassSmall Molecule
DescriptionNorgestimate was first described in the literature in 1977. It was developed by Ortho Pharmaceutical Corporation as part of an effort to develop new hormonal contraceptives with reduced adverse effects. It is commonly formulated with as a combined oral contraceptive that can also be used to treat moderate acne vulgaris. Norgestimate was granted FDA approval on 29 December 1989.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-2698000000-7e02d6124cbf30e8be87Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00di-0009000000-b5b2b147e5ce033804a6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-1bb2450b5dc4140f5e93Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00di-0209000000-c0873e43f4129a09814dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00di-0922000000-9b40bb72db6c044b370cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00di-0922000000-59c3543a046f1a654729Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-05i3-0910000000-6a2449a24f6efdf10513Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-cda4a2de67f83fe17601Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0129000000-e3b5fba490277d952c9eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-6491000000-51d7c89ce72eb09d3993Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016r-1009000000-2b5a8cbd62430bb58addSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05r0-2009000000-05bf9254a578ac3a1a11Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4029000000-76a6829838c24ac7bd2cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0019000000-ffdfef9c7bc973ccee83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0293000000-fcd7c087298d41406df8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01qa-0930000000-01441e5a4930cf72a343Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-3009000000-8b4cc4a89faf8b738f0eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0049000000-27e791a48fed12ec9d0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfs-2049000000-4e6f026ed6781f5b8b3bSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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