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Showing Compound androst-4-en-3,17-dione (FDB030678)

Record Information
Version1.0
Creation date2015-05-07 19:46:52 UTC
Update date2019-11-26 03:21:51 UTC
Primary IDFDB030678
Secondary Accession NumbersNot Available
Chemical Information
FooDB Nameandrost-4-en-3,17-dione
DescriptionAndrost-4-en-3,17-dione, also known as androstenedione or delta(4)-androsten-3,17-dione, belongs to androgens and derivatives class of compounds. Those 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. Thus, androst-4-en-3,17-dione is considered to be a steroid lipid molecule. Androst-4-en-3,17-dione is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Androst-4-en-3,17-dione can be found in a number of food items such as naranjilla, purslane, common cabbage, and oval-leaf huckleberry, which makes androst-4-en-3,17-dione a potential biomarker for the consumption of these food products. Androst-4-en-3,17-dione can be found primarily in blood, cerebrospinal fluid (CSF), and urine, as well as throughout most human tissues. In humans, androst-4-en-3,17-dione is involved in a couple of metabolic pathways, which include androgen and estrogen metabolism and androstenedione metabolism. Androst-4-en-3,17-dione is also involved in a couple of metabolic disorders, which include 17-beta hydroxysteroid dehydrogenase III deficiency and aromatase deficiency. Moreover, androst-4-en-3,17-dione is found to be associated with rheumatoid arthritis, thyroid cancer , cushing's Syndrome, and schizophrenia. Androst-4-en-3,17-dione is a non-carcinogenic (not listed by IARC) potentially toxic compound.
CAS Number63-05-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.027 g/LALOGPS
logP2.93ALOGPS
logP3.93ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)19.03ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.61 m³·mol⁻¹ChemAxon
Polarizability33.21 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC19H26O2
IUPAC name(1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione
InChI IdentifierInChI=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/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1
InChI KeyAEMFNILZOJDQLW-QAGGRKNESA-N
Isomeric SMILES[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
Average Molecular Weight286.4085
Monoisotopic Molecular Weight286.193280076
Classification
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-4-steroid
  • Delta-4-steroid
  • Cyclohexenone
  • 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 effect

Health effect:

Disposition

Route of exposure:

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Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-059m-3940000000-9cb32ac21e46afb2829a2014-09-20View Spectrum
GC-MSandrost-4-en-3,17-dione, non-derivatized, GC-MS Spectrumsplash10-004l-5910000000-518e1ad38bcc73325b53Spectrum
GC-MSandrost-4-en-3,17-dione, non-derivatized, GC-MS Spectrumsplash10-004l-5910000000-5172e05f9889ee2bfaf4Spectrum
GC-MSandrost-4-en-3,17-dione, non-derivatized, GC-MS Spectrumsplash10-000f-8940000000-f2892fe3b281d44164c8Spectrum
GC-MSandrost-4-en-3,17-dione, non-derivatized, GC-MS Spectrumsplash10-007d-1960000000-167f1765b095da9d603bSpectrum
GC-MSandrost-4-en-3,17-dione, non-derivatized, GC-MS Spectrumsplash10-004l-5910000000-518e1ad38bcc73325b53Spectrum
GC-MSandrost-4-en-3,17-dione, non-derivatized, GC-MS Spectrumsplash10-004l-5910000000-5172e05f9889ee2bfaf4Spectrum
Predicted GC-MSandrost-4-en-3,17-dione, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-0590000000-502d6b821317a01a1990Spectrum
Predicted GC-MSandrost-4-en-3,17-dione, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0090000000-36e848ba16b141eef47b2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052b-9600000000-712954fc35a84c8217de2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-052b-9300000000-f8e9aa16b4b208b69f7b2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-000f-8940000000-e12025ea2b7808c64b9c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-052b-6910000000-b616785c86a92f46158e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-052b-9800000000-73e545a1eb2232d553712017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00kb-5790000000-735473bc44dd70e292592017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00kb-5790000000-114675a4457063901f2b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 55V, Positivesplash10-052b-7910000000-f0d8591998137c42f7172021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-00kb-5790000000-f47366cff1ef472534552021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 80V, Positivesplash10-052b-9800000000-58ced8830fbdd255377e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 55V, Positivesplash10-00kb-5790000000-4d32bf4d34aaef92de912021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-052b-9700000000-5a645018a15e2dd1adeb2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-052b-9500000000-70913f3a4e21abdcf9ee2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-052b-9500000000-1405c9c7f6ea07c8d1e42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-eec15e6fd9d08b27ef072021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-778071650dcadc3b30692021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-00c3-0900000000-faf22b1b9717d889edd82021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00ei-0940000000-930c091a3d14712216532021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0190000000-0347db9e9578e8d5d6f22017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05pc-0490000000-d4049441f1c172450dc32017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uk9-4790000000-355bc0834a6465ecad302017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-887b6f223b77c683ef992017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-9dafdd780cca012f1fb32017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mo-2190000000-264074b1eefeed0e31032017-07-26View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference