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Showing metabocard for 5a-Dihydrotestosterone sulfate (HMDB0006278)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-22 21:03:43 UTC
Update Date2021-09-14 15:40:13 UTC
HMDB IDHMDB0006278
Secondary Accession Numbers
  • HMDB06278
Metabolite Identification
Common Name5a-Dihydrotestosterone sulfate
Description5a-Dihydrotestosterone sulfate is a sulfate derivative of 5a-Dihydrotestosterone produced through phase II metabolism. 5a-dihydrotestosterone (DHT) is a steroid similar to testosterone and androstenedione, that belongs to a class called androgens. DHT is a C19 steroid and possesses androgenic activity. Androgen production takes place mainly in the Leydig cells of the testes. Androgens circulate in the blood bound to proteins, especially sex hormone binding globulin (SHBG) and albumin. A trace amount of these steroids circulate in the unbound form in the blood and are referred to as the free fractions. DHT has at least three times the binding affinity for SHBG than testosterone. About 70% of DHT is derived from peripheral conversion of testosterone in males, while most of the DHT is derived from androstenedione in females.
Structure
Data?1582752378
MOLSDFPDBSMILESInChI

MOL for HMDB0006278 (5a-Dihydrotestosterone sulfate)

Not Available

3D MOL for HMDB0006278 (5a-Dihydrotestosterone sulfate)

Not Available

3D SDF for HMDB0006278 (5a-Dihydrotestosterone sulfate)

Not Available

3D-SDF for HMDB0006278 (5a-Dihydrotestosterone sulfate)

Not Available

PDB for HMDB0006278 (5a-Dihydrotestosterone sulfate)

Not Available

3D PDB for HMDB0006278 (5a-Dihydrotestosterone sulfate)

Not Available

SMILES for HMDB0006278 (5a-Dihydrotestosterone sulfate)

Not Available

INCHI for HMDB0006278 (5a-Dihydrotestosterone sulfate)

Not Available
View in JSmolView Stereo Labels
SynonymsNot Available
Chemical FormulaC19H30O5S
Average Molecular Weight370.504
Monoisotopic Molecular Weight370.18139476
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILESNot Available
InChI Identifier
InChI=1S/C19H30O5S/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(24-25(21,22)23)19(15,2)10-8-16(14)18/h12,14-17H,3-11H2,1-2H3,(H,21,22,23)/t12-,14-,15-,16-,17-,18-,19-/m0/s1
InChI KeyKYVPWJSGFKNNLD-ABEVXSGRSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties
Predicted Molecular PropertiesNot Available
Predicted Chromatographic Properties

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.7.28 minutes32390414
Predicted by Siyang on May 30, 202217.9775 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.7 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid2797.0 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid444.3 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid220.2 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid199.6 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid591.8 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid719.8 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid806.3 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)91.7 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1400.3 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid511.4 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1688.1 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid400.1 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid471.2 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate291.8 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA378.7 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water43.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5a-Dihydrotestosterone sulfate[H][C@@]12CC[C@H](OS(O)(=O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C3251.4Standard polar33892256
5a-Dihydrotestosterone sulfate[H][C@@]12CC[C@H](OS(O)(=O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C2905.7Standard non polar33892256
5a-Dihydrotestosterone sulfate[H][C@@]12CC[C@H](OS(O)(=O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C3182.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5a-Dihydrotestosterone sulfate,1TMS,isomer #1C[C@]12CCC(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@H]123088.1Semi standard non polar33892256
5a-Dihydrotestosterone sulfate,1TMS,isomer #1C[C@]12CCC(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@H]123069.4Standard non polar33892256
5a-Dihydrotestosterone sulfate,1TMS,isomer #1C[C@]12CCC(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@H]123744.1Standard polar33892256
5a-Dihydrotestosterone sulfate,1TMS,isomer #2C[C@]12CC=C(O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O)CC[C@@H]123112.9Semi standard non polar33892256
5a-Dihydrotestosterone sulfate,1TMS,isomer #2C[C@]12CC=C(O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O)CC[C@@H]122989.9Standard non polar33892256
5a-Dihydrotestosterone sulfate,1TMS,isomer #2C[C@]12CC=C(O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O)CC[C@@H]123847.5Standard polar33892256
5a-Dihydrotestosterone sulfate,1TMS,isomer #3C[C@]12CC[C@H]3[C@@H](CC[C@H]4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O3107.0Semi standard non polar33892256
5a-Dihydrotestosterone sulfate,1TMS,isomer #3C[C@]12CC[C@H]3[C@@H](CC[C@H]4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O3007.0Standard non polar33892256
5a-Dihydrotestosterone sulfate,1TMS,isomer #3C[C@]12CC[C@H]3[C@@H](CC[C@H]4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O3839.7Standard polar33892256
5a-Dihydrotestosterone sulfate,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@H]4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O[Si](C)(C)C3108.3Semi standard non polar33892256
5a-Dihydrotestosterone sulfate,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@H]4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O[Si](C)(C)C3208.4Standard non polar33892256
5a-Dihydrotestosterone sulfate,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@H]4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O[Si](C)(C)C3794.7Standard polar33892256
5a-Dihydrotestosterone sulfate,2TMS,isomer #2C[C@]12CC=C(O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@H]123115.4Semi standard non polar33892256
5a-Dihydrotestosterone sulfate,2TMS,isomer #2C[C@]12CC=C(O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@H]123192.5Standard non polar33892256
5a-Dihydrotestosterone sulfate,2TMS,isomer #2C[C@]12CC=C(O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@H]123796.6Standard polar33892256
5a-Dihydrotestosterone sulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C3308.3Semi standard non polar33892256
5a-Dihydrotestosterone sulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C3377.8Standard non polar33892256
5a-Dihydrotestosterone sulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C3864.4Standard polar33892256
5a-Dihydrotestosterone sulfate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O)CC[C@@H]32)C13396.2Semi standard non polar33892256
5a-Dihydrotestosterone sulfate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O)CC[C@@H]32)C13285.8Standard non polar33892256
5a-Dihydrotestosterone sulfate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O)CC[C@@H]32)C13987.1Standard polar33892256
5a-Dihydrotestosterone sulfate,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](OS(=O)(=O)O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC13375.5Semi standard non polar33892256
5a-Dihydrotestosterone sulfate,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](OS(=O)(=O)O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC13311.7Standard non polar33892256
5a-Dihydrotestosterone sulfate,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](OS(=O)(=O)O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC13980.2Standard polar33892256
5a-Dihydrotestosterone sulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@@H]32)C13589.0Semi standard non polar33892256
5a-Dihydrotestosterone sulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@@H]32)C13749.7Standard non polar33892256
5a-Dihydrotestosterone sulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@@H]32)C13954.5Standard polar33892256
5a-Dihydrotestosterone sulfate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC13559.9Semi standard non polar33892256
5a-Dihydrotestosterone sulfate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC13774.4Standard non polar33892256
5a-Dihydrotestosterone sulfate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC13951.8Standard polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
External LinksNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Purvis K, Saksena SK, Landgren BM, Cekan Z, Diczfalusy E: Steroid conjugates in human seminal plasma. Clin Endocrinol (Oxf). 1976 May;5(3):253-61. [PubMed:133773 ]
  2. Purvis K, Saksena SK, Cekan Z, Diczfalusy E, Giner J: Endocrine effects of vasectomy. Clin Endocrinol (Oxf). 1976 May;5(3):263-72. [PubMed:133774 ]
  3. Zhao X, Xu F, Qi B, Hao S, Li Y, Li Y, Zou L, Lu C, Xu G, Hou L: Serum metabolomics study of polycystic ovary syndrome based on liquid chromatography-mass spectrometry. J Proteome Res. 2014 Feb 7;13(2):1101-11. doi: 10.1021/pr401130w. Epub 2014 Jan 24. [PubMed:24428203 ]
  4. Sanchez-Guijo A, Oji V, Hartmann MF, Traupe H, Wudy SA: Simultaneous quantification of cholesterol sulfate, androgen sulfates, and progestagen sulfates in human serum by LC-MS/MS. J Lipid Res. 2015 Sep;56(9):1843-51. doi: 10.1194/jlr.D061499. Epub 2015 Aug 2. [PubMed:26239050 ]
  5. Xu H, Zheng X, Qian Y, Guan J, Yi H, Zou J, Wang Y, Meng L, Zhao A, Yin S, Jia W: Metabolomics Profiling for Obstructive Sleep Apnea and Simple Snorers. Sci Rep. 2016 Aug 2;6:30958. doi: 10.1038/srep30958. [PubMed:27480913 ]
  6. Dehennin L, Jondet M, Scholler R: Androgen and 19-norsteroid profiles in human preovulatory follicles from stimulated cycles: an isotope dilution-mass spectrometric study. J Steroid Biochem. 1987 Mar;26(3):399-405. [PubMed:3586654 ]
  7. Gibb W, Jeffery J: 5 -dihydrotestosterone sulphate and cortisone reductase. Biochim Biophys Acta. 1972 Dec 8;280(4):646-51. [PubMed:4648789 ]