Showing metabocard for Danazol (BMDB0002835)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:01:50 UTC
Update Date2020-04-22 15:11:27 UTC
BMDB IDBMDB0002835
Secondary Accession Numbers
  • BMDB02835
Metabolite Identification
Common NameDanazol
DescriptionDanazol, also known as danocrine or cyclomen, belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton. Danazol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
CyclomenChEBI
DanazolumChEBI
DanocrineChEBI
(17a)-Pregna-2,4-dien-20-yno[2,3-D]isoxazol-17-olHMDB
1-Ethynyl-2,3,3a,3b,4,5,10,10a,10b,11,12,12a-dodecahydro-10a,12a-dimethyl-1H-cyclopenta[7,8]phenanthro[3,2-D]isoxazol-1-olHMDB
17 alpha-Pregna-2,4-dien-20-yno[2,3-D] isoxazol-17 beta-olHMDB
17a-Pregna-2,4-dien-20-yne-[2,3-D]isoxazole-17b-olHMDB
17a-Pregna-2,4-dien-20-yno[2,3-D]isoxazol-17-olHMDB
1H-Cyclopenta[7,8]phenanthro[3,2-D]isoxazole- pregna-2,4-dien-20-yno[2,3-D]isoxazol-17-ol deriv.HMDB
BonzolHMDB
ChronogynHMDB
DanolHMDB
DanovaolHMDB
DanzolHMDB
LadogalHMDB
WinobaninHMDB
Alphapharm brand OF danazolHMDB
Kendrick brand OF danazolHMDB
Sanofi brand OF danazolHMDB
DanatrolHMDB
DanazantHMDB
Danazol-ratiopharmHMDB
DanovalHMDB
Ratiopharm brand OF danazolHMDB
Antigen brand OF danazolHMDB
AzolHMDB
NorcidenHMDB
PanacrineHMDB
Sanofi synthelabo brand OF danazolHMDB
Sanofi winthrop brand OF danazolHMDB
Danazol ratiopharmHMDB
Chemical FormulaC22H27NO2
Average Molecular Weight337.4553
Monoisotopic Molecular Weight337.204179113
IUPAC Name(1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.0^{2,10}.0^{4,8}.0^{14,18}]icosa-4(8),5,9-trien-17-ol
Traditional Name(1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.0^{2,10}.0^{4,8}.0^{14,18}]icosa-4(8),5,9-trien-17-ol
CAS Registry Number17230-88-5
SMILES
[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC3=C(C[C@]12C)C=NO3
InChI Identifier
InChI=1S/C22H27NO2/c1-4-22(24)10-8-18-16-6-5-15-11-19-14(13-23-25-19)12-20(15,2)17(16)7-9-21(18,22)3/h1,11,13,16-18,24H,5-10,12H2,2-3H3/t16-,17+,18+,20+,21+,22+/m1/s1
InChI KeyPOZRVZJJTULAOH-LHZXLZLDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrane steroids
Alternative Parents
Substituents
  • Estrane-skeleton
  • Hydroxysteroid
  • 17-hydroxysteroid
  • Ynone
  • Heteroaromatic compound
  • Azole
  • Cyclic alcohol
  • Tertiary alcohol
  • Isoxazole
  • Acetylide
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point225.6 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP4.081Not Available
Predicted Properties
PropertyValueSource
logP3.62ALOGPS
logP3.46ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)17.59ChemAxon
pKa (Strongest Basic)0.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.26 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity98.54 m³·mol⁻¹ChemAxon
Polarizability38.44 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-0669000000-7afc135d5b1e92134191View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-000x-2479000000-d5f94bb7e7215a30f820View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0009000000-9e745b8feecd354f6618View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-01b9-6902000000-854476472755ef5419e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9100000000-0d62c0c1b53c1cea5a25View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0329000000-56adc37fd83dfa3c686fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-05ia-3931000000-1490f6c4984a84016076View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-002f-6900000000-529d2d24864b26fdd611View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-002f-6900000000-01f21f6ea357e6649d15View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000i-1309000000-271d4ce8113e1bf16016View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-00dj-2910000000-3af637f5ddbf8cfd6b84View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-00dj-2920000000-ba6bb4b948be2171d864View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-05tg-3900000000-29df3c1f08b04956955dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-000i-0009000000-5fc69729a45a40e94073View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-002f-4900000000-7ba349192301fd4e5013View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-05tg-3900000000-a692616aee182eeb1270View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0119000000-d7acb78e38c02e285d4fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01wr-0289000000-2db311b410937e72f25aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000j-3690000000-5eb98df42b0016f9967aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-d1a89ea3e6c72ff1ab88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-71fbd4000b06296a8386View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00e9-2089000000-24b6d7f3ec074a6c2b59View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0019000000-2626c30d979a970252f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-007y-0982000000-4cf29ec44560862d68c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1001-1890000000-24565065bfdf6e8edf39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-8413c28ca2b1374741c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-3424fea43411af836104View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0002835
DrugBank IDDB01406
Phenol Explorer Compound IDNot Available
FooDB IDFDB023073
KNApSAcK IDNot Available
Chemspider ID26436
KEGG Compound IDC06938
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDanazol
METLIN IDNot Available
PubChem Compound28417
PDB IDNot Available
ChEBI ID4315
References
Synthesis ReferenceRaczkowska, Sabina; Lypacewicz, Maria K.; Chojecka-Koryn, Ewa; Jaworska, Romana; Wasiak, Teresa; Mozolowski, Felicjan; Wajcht, Jozef. Method of obtaining highly pure danazol. Pol. (1991), 3 pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available