19-Oxotestosterone (CHEM035607)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:55:25 UTC
Update Date2016-11-09 01:21:20 UTC
Accession NumberCHEM035607
Identification
Common Name19-Oxotestosterone
ClassSmall Molecule
Description19-Oxotestosterone 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. 19-Oxotestosterone exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. 19-Oxotestosterone participates in a number of enzymatic reactions, within cattle. In particular, 19-Oxotestosterone can be converted into estradiol and formic acid through its interaction with the enzyme cytochrome P450 19A1. In addition, 19-Oxotestosterone can be biosynthesized from 19-hydroxytestosterone; which is catalyzed by the enzyme cytochrome P450 19A1. In cattle, 19-oxotestosterone is involved in the metabolic pathway called the androgen and estrogen metabolism pathway.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC19H28O2
Average Molecular Mass288.424 g/mol
Monoisotopic Mass288.209 g/mol
CAS Registry Number4075-13-2
IUPAC Name(1S,2S,10S,11S,14S,15S)-14-hydroxy-15-methyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-2-carbaldehyde
Traditional Name19-oxotestosterone
SMILES[H][C@@]1(O)CC[C@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C
InChI IdentifierInChI=1S/C19H28O2/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/h11,14-17,21H,3-10H2,1-2H3/t14-,15+,16-,17+,18-,19-/m0/s1
InChI KeyMUMGGOZAMZWBJJ-WXJALIKYSA-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
  • 19-oxosteroid
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • 17-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aldehyde
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • 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 Solubility0.05 g/LALOGPS
logP2.32ALOGPS
logP2.4ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)18.29ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity85.22 m³·mol⁻¹ChemAxon
Polarizability33.95 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, Positivesplash10-00di-1190000000-38a46782f3a05e410638Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0592-2169000000-be11c2989577a025bcebSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0095000000-f1b4c5073a1a349142cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ktr-0191000000-787c331104e02697f82eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-4290000000-c3ebd3f84fc5f2a0f1adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0039000000-fcbe7a10b70f243584caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-0098000000-88bd42d7a3c0ee3d7238Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fs-0090000000-e5ab8ef14971dd3b053aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0029000000-ab4e4333433d95463751Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0190000000-58b8fdd5c28b55834da9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aba-0900000000-a07aa8a9e25f2da78867Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0019000000-e1aa2d5a1d9cdeff04e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pi0-0093000000-1d8018c21ff4c38691c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-0290000000-794f96d5ceb67c29f858Spectrum
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 IDNot Available
HMDB IDHMDB0003959
FooDB IDFDB030283
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc ID19-OXO-TESTOSTERONE
METLIN ID6991
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID13628409
ChEBI ID75308
PubChem Compound ID7048589
Kegg Compound IDC05295
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Benson, Harvey Douglas; Grunwell, Joyce Francis; Johnston, John O'Neal; Petrow, Vladimir. Compositions for inducing an estrogenic response. Belg. (1977), 32 pp.
2. Handelsman DJ: Clinical review: The rationale for banning human chorionic gonadotropin and estrogen blockers in sport. J Clin Endocrinol Metab. 2006 May;91(5):1646-53. Epub 2006 Feb 14.
3. Mazer N, Fisher D, Fischer J, Cosgrove M, Bell D, Eilers B: Transfer of transdermally applied testosterone to clothing: a comparison of a testosterone patch versus a testosterone gel. J Sex Med. 2005 Mar;2(2):227-34.
4. Pasqualotto FF, Lucon AM, de Goes PM, Sobreiro BP, Hallak J, Pasqualotto EB, Arap S: Relationship between the number of veins ligated in a varicocelectomy with testicular volume, hormonal levels and semen parameters outcome. J Assist Reprod Genet. 2005 Jun;22(6):245-9.
5. Schaap LA, Pluijm SM, Smit JH, van Schoor NM, Visser M, Gooren LJ, Lips P: The association of sex hormone levels with poor mobility, low muscle strength and incidence of falls among older men and women. Clin Endocrinol (Oxf). 2005 Aug;63(2):152-60.
6. Huang I, Jones J, Khorram O: Human seminal plasma nitric oxide: correlation with sperm morphology and testosterone. Med Sci Monit. 2006 Mar;12(3):CR103-6. Epub 2006 Feb 23.
7. Ahtiainen JP, Pakarinen A, Alen M, Kraemer WJ, Hakkinen K: Short vs. long rest period between the sets in hypertrophic resistance training: influence on muscle strength, size, and hormonal adaptations in trained men. J Strength Cond Res. 2005 Aug;19(3):572-82.
8. Tan U: Testosterone and somatosensory evoked potentials from right and left posterior tibial nerves in right-handed young adults. Int J Neurosci. 1990 Dec;55(2-4):161-70.
9. Fejes I, Koloszar S, Szollosi J, Zavaczki Z, Pal A: Is semen quality affected by male body fat distribution? Andrologia. 2005 Oct;37(5):155-9.
10. Jarow JP, Zirkin BR: The androgen microenvironment of the human testis and hormonal control of spermatogenesis. Ann N Y Acad Sci. 2005 Dec;1061:208-20.
11. Klimek M, Pabian W, Tomaszewska B, Kolodziejczyk J: Levels of plasma ACTH in men from infertile couples. Neuro Endocrinol Lett. 2005 Aug;26(4):347-50.
12. Fournier P, Boissier S, Filleur S, Guglielmi J, Cabon F, Colombel M, Clezardin P: Bisphosphonates inhibit angiogenesis in vitro and testosterone-stimulated vascular regrowth in the ventral prostate in castrated rats. Cancer Res. 2002 Nov 15;62(22):6538-44.
13. Dicker A, Ryden M, Naslund E, Muehlen IE, Wiren M, Lafontan M, Arner P: Effect of testosterone on lipolysis in human pre-adipocytes from different fat depots. Diabetologia. 2004 Mar;47(3):420-428. doi: 10.1007/s00125-003-1324-0. Epub 2004 Jan 30.
14. Sipila S, Heikkinen E, Cheng S, Suominen H, Saari P, Kovanen V, Alen M, Rantanen T: Endogenous hormones, muscle strength, and risk of fall-related fractures in older women. J Gerontol A Biol Sci Med Sci. 2006 Jan;61(1):92-6.
15. Ferrando AA, Sheffield-Moore M, Wolf SE, Herndon DN, Wolfe RR: Testosterone administration in severe burns ameliorates muscle catabolism. Crit Care Med. 2001 Oct;29(10):1936-42.
16. Martinez-Riera A, Santolaria-Fernandez F, Gonzalez Reimers E, Milena A, Gomez-Sirvent JL, Rodriguez-Moreno F, Gonzalez-Martin I, Rodriguez-Rodriguez E: Alcoholic hypogonadism: hormonal response to clomiphene. Alcohol. 1995 Nov-Dec;12(6):581-7.
17. Ebert T, Jockenhovel F, Morales A, Shabsigh R: The current status of therapy for symptomatic late-onset hypogonadism with transdermal testosterone gel. Eur Urol. 2005 Feb;47(2):137-46.
18. Shores MM, Matsumoto AM, Sloan KL, Kivlahan DR: Low serum testosterone and mortality in male veterans. Arch Intern Med. 2006 Aug 14-28;166(15):1660-5.
19. Bhasin S, Cunningham GR, Hayes FJ, Matsumoto AM, Snyder PJ, Swerdloff RS, Montori VM: Testosterone therapy in adult men with androgen deficiency syndromes: an endocrine society clinical practice guideline. J Clin Endocrinol Metab. 2006 Jun;91(6):1995-2010. Epub 2006 May 23.
20. Jarow JP, Wright WW, Brown TR, Yan X, Zirkin BR: Bioactivity of androgens within the testes and serum of normal men. J Androl. 2005 May-Jun;26(3):343-8.
21. Lottrup G, Andersson AM, Leffers H, Mortensen GK, Toppari J, Skakkebaek NE, Main KM: Possible impact of phthalates on infant reproductive health. Int J Androl. 2006 Feb;29(1):172-80; discussion 181-5.
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=2317517
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=2363692
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=3857612