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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-21 06:16:28 UTC
Update Date2022-03-07 03:17:54 UTC
HMDB IDHMDB0062415
Secondary Accession Numbers
  • HMDB62415
Metabolite Identification
Common Nameandrost-5-ene-3,17-dione
Descriptionandrost-5-ene-3,17-dione, also known as delta5-ADD or δ5-add, is classified as an androgen or an Androgen derivative. Androgens are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. androst-5-ene-3,17-dione is considered to be practically insoluble (in water) and relatively neutral
Structure
Data?1563866308
Synonyms
ValueSource
5-Androstene-3,17-dioneChEBI
Delta(5)-Androstene-3,17-dioneChEBI
delta5-Androstene-3,17-dioneChEBI
Δ(5)-androstene-3,17-dioneGenerator
Δ5-androstene-3,17-dioneGenerator
Chemical FormulaC19H26O2
Average Molecular Weight286.415
Monoisotopic Molecular Weight286.193280077
IUPAC Name(1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,14-dione
Traditional Name(1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,14-dione
CAS Registry Number571-36-8
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C19H26O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,14-16H,4-11H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1
InChI KeySQGZFRITSMYKRH-QAGGRKNESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • Oxosteroid
  • 17-oxosteroid
  • 3-oxosteroid
  • 3-oxo-delta-5-steroid
  • Delta-5-steroid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.037 g/lALOGPS
LogP3.21ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP3.21ALOGPS
logP3.57ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)16.23ChemAxon
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.63 m³·mol⁻¹ChemAxon
Polarizability33.23 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]+170.85231661259
DarkChem[M-H]-165.44331661259
DeepCCS[M-2H]-202.63230932474
DeepCCS[M+Na]+176.84730932474
AllCCS[M+H]+172.832859911
AllCCS[M+H-H2O]+169.632859911
AllCCS[M+NH4]+175.732859911
AllCCS[M+Na]+176.632859911
AllCCS[M-H]-178.332859911
AllCCS[M+Na-2H]-178.332859911
AllCCS[M+HCOO]-178.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
androst-5-ene-3,17-dione[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CC(=O)CC[C@]12C2820.1Standard polar33892256
androst-5-ene-3,17-dione[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CC(=O)CC[C@]12C2467.6Standard non polar33892256
androst-5-ene-3,17-dione[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CC(=O)CC[C@]12C2585.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
androst-5-ene-3,17-dione,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4CC(=O)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2636.4Semi standard non polar33892256
androst-5-ene-3,17-dione,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4CC(=O)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2463.6Standard non polar33892256
androst-5-ene-3,17-dione,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4CC(=O)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2886.3Standard polar33892256
androst-5-ene-3,17-dione,1TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC=C4CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CCC2=O2635.6Semi standard non polar33892256
androst-5-ene-3,17-dione,1TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC=C4CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CCC2=O2520.4Standard non polar33892256
androst-5-ene-3,17-dione,1TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC=C4CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CCC2=O2991.3Standard polar33892256
androst-5-ene-3,17-dione,1TMS,isomer #3C[C@]12CC[C@H]3[C@@H](CC=C4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CCC2=O2671.1Semi standard non polar33892256
androst-5-ene-3,17-dione,1TMS,isomer #3C[C@]12CC[C@H]3[C@@H](CC=C4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CCC2=O2599.3Standard non polar33892256
androst-5-ene-3,17-dione,1TMS,isomer #3C[C@]12CC[C@H]3[C@@H](CC=C4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CCC2=O3015.3Standard polar33892256
androst-5-ene-3,17-dione,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2682.1Semi standard non polar33892256
androst-5-ene-3,17-dione,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2578.1Standard non polar33892256
androst-5-ene-3,17-dione,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2962.9Standard polar33892256
androst-5-ene-3,17-dione,2TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC=C4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2738.2Semi standard non polar33892256
androst-5-ene-3,17-dione,2TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC=C4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2648.4Standard non polar33892256
androst-5-ene-3,17-dione,2TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC=C4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C3004.2Standard polar33892256
androst-5-ene-3,17-dione,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC=C4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C2885.0Semi standard non polar33892256
androst-5-ene-3,17-dione,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC=C4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C2616.0Standard non polar33892256
androst-5-ene-3,17-dione,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC=C4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C3047.6Standard polar33892256
androst-5-ene-3,17-dione,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]32)C12885.5Semi standard non polar33892256
androst-5-ene-3,17-dione,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]32)C12734.8Standard non polar33892256
androst-5-ene-3,17-dione,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]32)C13143.7Standard polar33892256
androst-5-ene-3,17-dione,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC2=CC[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC12921.0Semi standard non polar33892256
androst-5-ene-3,17-dione,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC2=CC[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC12823.7Standard non polar33892256
androst-5-ene-3,17-dione,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC2=CC[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC13170.4Standard polar33892256
androst-5-ene-3,17-dione,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC=C(O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]32)C13219.1Semi standard non polar33892256
androst-5-ene-3,17-dione,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC=C(O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]32)C12850.9Standard non polar33892256
androst-5-ene-3,17-dione,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC=C(O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]32)C13202.6Standard polar33892256
androst-5-ene-3,17-dione,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC2=CC[C@H]3[C@@H]4CC=C(O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC13237.1Semi standard non polar33892256
androst-5-ene-3,17-dione,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC2=CC[C@H]3[C@@H]4CC=C(O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC12938.4Standard non polar33892256
androst-5-ene-3,17-dione,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC2=CC[C@H]3[C@@H]4CC=C(O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC13250.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - androst-5-ene-3,17-dione GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-0390000000-760e3af08c182fe0a7a82017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - androst-5-ene-3,17-dione GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - androst-5-ene-3,17-dione GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - androst-5-ene-3,17-dione 10V, Positive-QTOFsplash10-000i-0190000000-345528e1582c3af702212017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - androst-5-ene-3,17-dione 20V, Positive-QTOFsplash10-05pc-0490000000-ab4bc66eeb37b3d2c4032017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - androst-5-ene-3,17-dione 40V, Positive-QTOFsplash10-0w4j-2890000000-dbe08175bd667d0fdcbb2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - androst-5-ene-3,17-dione 10V, Negative-QTOFsplash10-000i-0090000000-d6f4af13bb58272885132017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - androst-5-ene-3,17-dione 20V, Negative-QTOFsplash10-000i-0090000000-80b339c485bd38625c192017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - androst-5-ene-3,17-dione 40V, Negative-QTOFsplash10-05mo-3190000000-ba08d022265f023bf6d52017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - androst-5-ene-3,17-dione 10V, Positive-QTOFsplash10-000i-0090000000-2b9c612ca0a0402e57212021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - androst-5-ene-3,17-dione 20V, Positive-QTOFsplash10-1000-0390000000-979afa8c7116bf2cca6d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - androst-5-ene-3,17-dione 40V, Positive-QTOFsplash10-0a4l-4900000000-f149fa8af7691dce05da2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - androst-5-ene-3,17-dione 10V, Negative-QTOFsplash10-000i-0090000000-69c80a26e4f51bb27abb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - androst-5-ene-3,17-dione 20V, Negative-QTOFsplash10-000i-0090000000-69c80a26e4f51bb27abb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - androst-5-ene-3,17-dione 40V, Negative-QTOFsplash10-0uei-1290000000-1e4a1c47b26b3ac4099f2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01456
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID141063
KEGG Compound IDC20252
BioCyc IDCPD66-29
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound160531
PDB IDNot Available
ChEBI ID83865
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.