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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-06 16:21:47 UTC
Update Date2021-09-16 15:27:41 UTC
HMDB IDHMDB0006769
Secondary Accession Numbers
  • HMDB06769
Metabolite Identification
Common Name19-Hydroxytestosterone
DescriptionIndole-5,6-quinone belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Indole-5,6-quinone is a strong basic compound (based on its pKa). Indole-5,6-quinone exists in all living organisms, ranging from bacteria to humans. indole-5,6-quinone can be biosynthesized from 5,6-dihydroxyindole through the action of the enzyme tyrosinase. In humans, indole-5,6-quinone is involved in the metabolic disorder called hawkinsinuria. Outside of the human body, Indole-5,6-quinone has been detected, but not quantified in, milk (cow). This could make indole-5,6-quinone a potential biomarker for the consumption of these foods.
Structure
Data?1582752405
Synonyms
ValueSource
1H-Indole-5,6-dioneHMDB
Indole-5,6 quinoneHMDB
17beta,19-Dihydroxyandrost-4-en-3-oneHMDB
Chemical FormulaC19H28O3
Average Molecular Weight304.4238
Monoisotopic Molecular Weight304.203844762
IUPAC Name(2S,10R,14S,15S)-14-hydroxy-2-(hydroxymethyl)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Name(2S,10R,14S,15S)-14-hydroxy-2-(hydroxymethyl)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
CAS Registry Number2126-37-6
SMILES
[H]C12CC[C@H](O)[C@@]1(C)CCC1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12CO
InChI Identifier
InChI=1S/C19H28O3/c1-18-8-7-16-14(15(18)4-5-17(18)22)3-2-12-10-13(21)6-9-19(12,16)11-20/h10,14-17,20,22H,2-9,11H2,1H3/t14-,15?,16?,17-,18-,19+/m0/s1
InChI KeyYLTCTXBDDHSLCS-HRCCTRRKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassNot Available
Direct ParentIndoles and derivatives
Alternative Parents
Substituents
  • Indole or derivatives
  • Pyrrole
  • Vinylogous amide
  • Heteroaromatic compound
  • Ketone
  • Cyclic ketone
  • Azacycle
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.064 g/LALOGPS
logP10(1.93) g/LALOGPS
logP10(2.08) g/LChemAxon
logS10(-3.7) g/LALOGPS
pKa (Strongest Acidic)18.74ChemAxon
pKa (Strongest Basic)-0.62ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity86.2 m³·mol⁻¹ChemAxon
Polarizability34.77 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+169.69931661259
DarkChem[M-H]-165.18931661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
19-Hydroxytestosterone,1TMS,#1C[C@]12CCC3[C@@H](CCC4=CC(=O)CC[C@@]43CO)C1CC[C@@H]2O[Si](C)(C)C2942.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
19-Hydroxytestosterone,1TMS,#2C[C@]12CCC3[C@@H](CCC4=CC(=O)CC[C@@]43CO[Si](C)(C)C)C1CC[C@@H]2O2906.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
19-Hydroxytestosterone,1TMS,#3C[C@]12CCC3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43CO)C1CC[C@@H]2O2827.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
19-Hydroxytestosterone,2TMS,#1C[C@]12CCC3[C@@H](CCC4=CC(=O)CC[C@@]43CO[Si](C)(C)C)C1CC[C@@H]2O[Si](C)(C)C2933.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
19-Hydroxytestosterone,2TMS,#2C[C@]12CCC3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43CO)C1CC[C@@H]2O[Si](C)(C)C2852.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
19-Hydroxytestosterone,2TMS,#3C[C@]12CCC3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43CO[Si](C)(C)C)C1CC[C@@H]2O2838.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
19-Hydroxytestosterone,1TBDMS,#1CC(C)(C)[Si](C)(C)O[C@H]1CCC2[C@@H]3CCC4=CC(=O)CC[C@]4(CO)C3CC[C@@]21C3216.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
19-Hydroxytestosterone,1TBDMS,#2CC(C)(C)[Si](C)(C)OC[C@]12CCC(=O)C=C1CC[C@@H]1C2CC[C@@]2(C)C1CC[C@@H]2O3174.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
19-Hydroxytestosterone,1TBDMS,#3CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(CO)C(=C1)CC[C@@H]1C2CC[C@@]2(C)C1CC[C@@H]2O3114.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
19-Hydroxytestosterone,2TBDMS,#1CC(C)(C)[Si](C)(C)OC[C@]12CCC(=O)C=C1CC[C@@H]1C2CC[C@@]2(C)C1CC[C@@H]2O[Si](C)(C)C(C)(C)C3453.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
19-Hydroxytestosterone,2TBDMS,#2CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(CO)C(=C1)CC[C@@H]1C2CC[C@@]2(C)C1CC[C@@H]2O[Si](C)(C)C(C)(C)C3379.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
19-Hydroxytestosterone,2TBDMS,#3CC(C)(C)[Si](C)(C)OC[C@]12CC=C(O[Si](C)(C)C(C)(C)C)C=C1CC[C@@H]1C2CC[C@@]2(C)C1CC[C@@H]2O3316.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 19-Hydroxytestosterone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00g0-0190000000-6e4fc7b300ad16c455cd2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 19-Hydroxytestosterone GC-MS (2 TMS) - 70eV, Positivesplash10-001i-1203900000-4f90d6dd0388b3a160172017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 19-Hydroxytestosterone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 19-Hydroxytestosterone 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 - 19-Hydroxytestosterone 10V, Positive-QTOFsplash10-052r-0093000000-e6de474519f1a50b8a292017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Hydroxytestosterone 20V, Positive-QTOFsplash10-0670-0090000000-e998b159f6f17e76d6ff2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Hydroxytestosterone 40V, Positive-QTOFsplash10-0550-3590000000-c2362be82382a74f0ccb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Hydroxytestosterone 10V, Negative-QTOFsplash10-0udi-0059000000-22c9035dbc29099536802017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Hydroxytestosterone 20V, Negative-QTOFsplash10-0zmr-0094000000-a86f4275aef3909e642b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Hydroxytestosterone 40V, Negative-QTOFsplash10-05fs-0090000000-a227eb144908c8f752ba2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Hydroxytestosterone 10V, Positive-QTOFsplash10-0a4i-0019000000-96c876787125565560bb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Hydroxytestosterone 20V, Positive-QTOFsplash10-0a6r-0892000000-64923385891f1c2ddf282021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Hydroxytestosterone 40V, Positive-QTOFsplash10-0a4i-0900000000-9b70a6d7d0da7c6a6b3d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Hydroxytestosterone 10V, Negative-QTOFsplash10-0udi-0019000000-28d038f60bc762557a4d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Hydroxytestosterone 20V, Negative-QTOFsplash10-0udi-0039000000-b8ab70909d16db9663112021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Hydroxytestosterone 40V, Negative-QTOFsplash10-0ab9-0090000000-21047d70207f0666ac312021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024077
KNApSAcK IDNot Available
Chemspider ID389600
KEGG Compound IDC05579
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIndole-5,6-quinone
METLIN IDNot Available
PubChem Compound440728
PDB IDNot Available
ChEBI ID27406
Food Biomarker OntologyNot Available
VMH IDM03163
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Only showing the first 10 proteins. There are 24 proteins in total.

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
General function:
Involved in monooxygenase activity
Specific function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular weight:
56848.42
General function:
Involved in monooxygenase activity
Specific function:
Exhibits low testosterone 6-beta-hydroxylase activity.
Gene Name:
CYP3A43
Uniprot ID:
Q9HB55
Molecular weight:
57756.285
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Molecular weight:
60845.33
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP2C18
Uniprot ID:
P33260
Molecular weight:
55710.075
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
May be involved in the metabolism of various pneumotoxicants including naphthalene. Is able to dealkylate ethoxycoumarin, propoxycoumarin, and pentoxyresorufin but possesses no activity toward ethoxyresorufin and only trace dearylation activity toward benzyloxyresorufin. Bioactivates 3-methylindole (3MI) by dehydrogenation to the putative electrophile 3-methylene-indolenine.
Gene Name:
CYP2F1
Uniprot ID:
P24903
Molecular weight:
55500.64
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
CYP4X1
Uniprot ID:
Q8N118
Molecular weight:
58874.62
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular weight:
56277.81

Only showing the first 10 proteins. There are 24 proteins in total.