ANDROSTA-1,4-DIENE-3,17-DIONE

Identification

Name
ANDROSTA-1,4-DIENE-3,17-DIONE
Accession Number
DB07373
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
J38.935H / NSC-49080
Categories
UNII
2166Q8568W
CAS number
Not Available
Weight
Average: 284.3927
Monoisotopic: 284.177630012
Chemical Formula
C19H24O2
InChI Key
LUJVUUWNAPIQQI-QAGGRKNESA-N
InChI
InChI=1S/C19H24O2/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/h7,9,11,14-16H,3-6,8,10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1
IUPAC Name
(1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-diene-5,14-dione
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C=C[C@]12C

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UPentaerythritol tetranitrate reductaseNot AvailableEnterobacter cloacae
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Merle G. Wovcha, Candice B. Biggs, Thomas R. Pyke, "Process for preparing androsta-1,4-diene-3,17-dione and androst-4-ene-3,17-dione." U.S. Patent US4293645, issued July, 1977.

US4293645
General References
Not Available
External Links
Human Metabolome Database
HMDB0003422
PubChem Compound
13472
PubChem Substance
99443844
ChemSpider
12893
BindingDB
91718
ChEBI
40799
ChEMBL
CHEMBL1078534
HET
ANB
PDB Entries
1h62 / 4c3y

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0169 mg/mLALOGPS
logP2.78ALOGPS
logP3.93ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)18.83ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.7 m3·mol-1ChemAxon
Polarizability32.47 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9793
Caco-2 permeable+0.8011
P-glycoprotein substrateSubstrate0.5526
P-glycoprotein inhibitor IInhibitor0.8564
P-glycoprotein inhibitor IINon-inhibitor0.6615
Renal organic cation transporterNon-inhibitor0.6632
CYP450 2C9 substrateNon-substrate0.8548
CYP450 2D6 substrateNon-substrate0.9131
CYP450 3A4 substrateSubstrate0.7193
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9387
CYP450 2D6 inhibitorNon-inhibitor0.9386
CYP450 2C19 inhibitorNon-inhibitor0.8138
CYP450 3A4 inhibitorNon-inhibitor0.8483
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8067
Ames testNon AMES toxic0.9508
CarcinogenicityNon-carcinogens0.9313
BiodegradationNot ready biodegradable0.9343
Rat acute toxicity1.5360 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7599
hERG inhibition (predictor II)Non-inhibitor0.7469
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-APPI-QQ , positiveLC-MS/MSsplash10-0096-7900000000-0e538c3554828587687d
LC-MS/MS Spectrum - LC-APPI-QQ , positiveLC-MS/MSsplash10-00dm-3900000000-5d42203f518a99185773
LC-MS/MS Spectrum - LC-APPI-QQ , positiveLC-MS/MSsplash10-00dj-1900000000-19c879c287403c0ed2ef
LC-MS/MS Spectrum - LC-APPI-QQ , positiveLC-MS/MSsplash10-00dj-0910000000-004b73c2f16c9747052b
LC-MS/MS Spectrum - LC-APPI-QQ , positiveLC-MS/MSsplash10-00y1-0960000000-9c049fde9edd83e377b4
LC-MS/MS Spectrum - LC-APPI-QQ , positiveLC-MS/MSsplash10-000i-0090000000-59ad5b9288fa52be718c
LC-MS/MS Spectrum - LC-APPI-QQ , positiveLC-MS/MSsplash10-004l-5900000000-c06d7a1d1deabe2ff1f6
LC-MS/MS Spectrum - LC-APPI-QQ , positiveLC-MS/MSsplash10-05dl-4900000000-fa822a5bff16e6c79e5f
LC-MS/MS Spectrum - LC-APPI-QQ , positiveLC-MS/MSsplash10-00di-2910000000-d9af7cc7fbe8d5314eb4
LC-MS/MS Spectrum - LC-APPI-QQ , positiveLC-MS/MSsplash10-00di-1920000000-9967f8cfb367b47cc432
LC-MS/MS Spectrum - LC-APPI-QQ , positiveLC-MS/MSsplash10-014i-0790000000-0d6677503a198b1035c0
LC-MS/MS Spectrum - LC-APPI-QQ , positiveLC-MS/MSsplash10-014i-0090000000-696830f2bd076fad3e71
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-0910000000-f76cb8acbe3dda64f678

Taxonomy

Description
This compound 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Androstane steroids
Direct Parent
Androgens and derivatives
Alternative Parents
3-oxo delta-1,4-steroids / 17-oxosteroids / Delta-1,4-steroids / Cyclic ketones / Organic oxides / Hydrocarbon derivatives
Substituents
Androgen-skeleton / Oxosteroid / 17-oxosteroid / 3-oxosteroid / 3-oxo-delta-1,4-steroid / Delta-1,4-steroid / Cyclic ketone / Ketone / Organic oxygen compound / Organic oxide
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
3-oxo steroid, 17-oxo steroid (CHEBI:40799)

Targets

Kind
Protein
Organism
Enterobacter cloacae
Pharmacological action
Unknown
General Function
Oxidoreductase activity
Specific Function
Not Available
Gene Name
onr
Uniprot ID
P71278
Uniprot Name
Pentaerythritol tetranitrate reductase
Molecular Weight
39488.93 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on September 15, 2010 15:20 / Updated on November 02, 2018 06:31