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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-13 05:18:00 UTC
Update Date2022-09-22 18:34:17 UTC
HMDB IDHMDB0003818
Secondary Accession Numbers
  • HMDB03818
Metabolite Identification
Common Name5-Androstenediol
Description5-Androstenediol is a direct metabolite of the most abundant steroid produced by the human adrenal cortex, dehydroepiandrosterone (DHEA). 5-Androstenediol is less androgenic than 4-androstenediol, and stimulates the immune system. When administered to rats in vivo, 5-androstenediol has approximately 1/70 the androgenicity of DHEA, 1/185 the androgenicity of androstenedione, and 1/475 the androgenicity of testosterone (Wikipedia ). Because it induces production of white blood cells and platelets, 5-androstenediol is being developed as a radiation countermeasure as Neumune (HE2100). An intermediate in testosterone biosynthesis, found in the testis or the adrenal glands. 5-Androstenediol, derived from dehydroepiandrosterone by the reduction of the 17-keto group (17-hydroxysteroid dehydrogenases), is converted to testosterone by the oxidation of the 3-beta hydroxyl group to a 3-keto group (3-fydroxysteroid dehydrogenase).
Structure
Data?1582752287
Synonyms
ValueSource
(3beta,17beta)-Androst-5-ene-3,17-diolChEBI
3beta,17beta-Dihydroxy-5-androsteneChEBI
3beta,17beta-Dihydroxyandrost-5-eneChEBI
5-AndrostenediolChEBI
Androst-5-en-3beta,17beta-diolChEBI
Androst-5-enediolChEBI
HermaphrodiolChEBI
Androst-5-ene-3beta,17beta-diolKegg
TetrabolKegg
(3b,17b)-Androst-5-ene-3,17-diolGenerator
(3Β,17β)-androst-5-ene-3,17-diolGenerator
3b,17b-Dihydroxy-5-androsteneGenerator
3Β,17β-dihydroxy-5-androsteneGenerator
3b,17b-Dihydroxyandrost-5-eneGenerator
3Β,17β-dihydroxyandrost-5-eneGenerator
Androst-5-en-3b,17b-diolGenerator
Androst-5-en-3β,17β-diolGenerator
Androst-5-ene-3b,17b-diolGenerator
Androst-5-ene-3β,17β-diolGenerator
AndrostenediolChEBI
Androst-5-ene-3,17-diolHMDB
b,17b-DiolHMDB
delta-5-AndrostenediolHMDB
Delta5-AndrostenediolHMDB
5 Androstene 3,17 diolMeSH, HMDB
Delta 5-AndrostenediolMeSH, HMDB
Parke davis brand OF androstenediolMeSH, HMDB
delta 5-Androstene-3 beta,17 beta-diolMeSH, HMDB
5 Androstene 3beta 17beta diolMeSH, HMDB
Androst 5 ene 3 beta,17 beta diolMeSH, HMDB
Androst-5-ene-3 beta,17 beta-diolMeSH, HMDB
5-Androstene-3beta-17beta-diolMeSH, HMDB
BisexovisterMeSH, HMDB
Delta 5 AndrostenediolMeSH, HMDB
5-Androstene-3,17-diolMeSH, HMDB
Androst 5 ene 3,17 diolMeSH, HMDB
delta 5 Androstene 3 beta,17 beta diolMeSH, HMDB
Chemical FormulaC19H30O2
Average Molecular Weight290.4403
Monoisotopic Molecular Weight290.224580204
IUPAC Name(1S,2R,5S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,14-diol
Traditional Name5-androstenediol
CAS Registry Number521-17-5
SMILES
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C19H30O2/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/h3,13-17,20-21H,4-11H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1
InChI KeyQADHLRWLCPCEKT-LOVVWNRFSA-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
  • 17-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.055 g/LALOGPS
logP3.42ALOGPS
logP2.8ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-0.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity85.48 m³·mol⁻¹ChemAxon
Polarizability34.68 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+169.52931661259
DarkChem[M-H]-164.97631661259
DeepCCS[M-2H]-208.05630932474
DeepCCS[M+Na]+182.58230932474
AllCCS[M+H]+176.632859911
AllCCS[M+H-H2O]+173.532859911
AllCCS[M+NH4]+179.532859911
AllCCS[M+Na]+180.332859911
AllCCS[M-H]-178.832859911
AllCCS[M+Na-2H]-179.032859911
AllCCS[M+HCOO]-179.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-Androstenediol[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C2471.0Standard polar33892256
5-Androstenediol[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C2497.1Standard non polar33892256
5-Androstenediol[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C2609.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Androstenediol,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]1CC[C@@H]2O[Si](C)(C)C2607.7Semi standard non polar33892256
5-Androstenediol,1TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2O2601.2Semi standard non polar33892256
5-Androstenediol,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2O[Si](C)(C)C2658.0Semi standard non polar33892256
5-Androstenediol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C2891.1Semi standard non polar33892256
5-Androstenediol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]32)C12871.3Semi standard non polar33892256
5-Androstenediol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]32)C13205.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 5-Androstenediol GC-MS (2 TMS)splash10-004l-3920000000-6d05021a14366bfd40ba2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Androstenediol GC-MS (Non-derivatized)splash10-004l-3920000000-6d05021a14366bfd40ba2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Androstenediol GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ea-0190000000-3ceb1bf6f3d53ee5d7e52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Androstenediol GC-MS (2 TMS) - 70eV, Positivesplash10-014i-2126900000-1bc7293586fc53c1c4572017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Androstenediol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Androstenediol 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 - 5-Androstenediol 10V, Positive-QTOFsplash10-00dl-0090000000-551d3445a2c6cdfa61ee2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Androstenediol 20V, Positive-QTOFsplash10-05fr-0390000000-5cfc4d0f79fea1c885b82016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Androstenediol 40V, Positive-QTOFsplash10-02bf-3890000000-e55a0a62bc36fe9049ec2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Androstenediol 10V, Negative-QTOFsplash10-000i-0090000000-d1deb080063b126f79ce2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Androstenediol 20V, Negative-QTOFsplash10-0079-0090000000-4d0bb4d4f197bc1e68462016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Androstenediol 40V, Negative-QTOFsplash10-0abc-1190000000-3f4cb9035ceae26a48762016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Androstenediol 10V, Positive-QTOFsplash10-0006-0090000000-9de0edc3a8b815dd70712021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Androstenediol 20V, Positive-QTOFsplash10-0abd-1940000000-90cd37c36522659206782021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Androstenediol 40V, Positive-QTOFsplash10-0aos-1900000000-76460d7bb552466d15042021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Androstenediol 10V, Negative-QTOFsplash10-000i-0090000000-c8c452fd99c6bb4f36312021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Androstenediol 20V, Negative-QTOFsplash10-000i-0090000000-1ce9bb01eb35f26908c42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Androstenediol 40V, Negative-QTOFsplash10-000i-0090000000-aeda10893d01c46acf8c2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Adipose Tissue
  • Adrenal Cortex
  • Prostate
  • Skeletal Muscle
  • Testis
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Associated OMIM IDs
DrugBank IDDB01524
Phenol Explorer Compound IDNot Available
FooDB IDFDB023228
KNApSAcK IDNot Available
Chemspider ID10188
KEGG Compound IDC04295
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAndrostenediol
METLIN IDNot Available
PubChem Compound10634
PDB IDNot Available
ChEBI ID2710
Food Biomarker OntologyNot Available
VMH IDC04295
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceRistovic, Lj.; Cobanovic, M.; Jovanovic, Z.; Orlic, M. Synthesis of androstenediol and determination of its physicochemical constants. Kemija u Industriji (1975), 24(7), 389-92.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Weusten JJ, Smals AG, Hofman JA, Kloppenborg PW, Benraad TJ: Early time sequence in pregnenolone metabolism to testosterone in homogenates of human and rat testis. Endocrinology. 1987 May;120(5):1909-13. [PubMed:3569120 ]
  2. Leszczynski DE, Schafer RM: Characterization of steroid hormone association with human plasma lipoproteins. Steroids. 1989 Jul;54(1):37-53. [PubMed:2815156 ]
  3. Szymczak J, Milewicz A, Thijssen JH, Blankenstein MA, Daroszewski J: Concentration of sex steroids in adipose tissue after menopause. Steroids. 1998 May-Jun;63(5-6):319-21. [PubMed:9618794 ]
  4. Tchernof A, Despres JP, Belanger A, Dupont A, Prud'homme D, Moorjani S, Lupien PJ, Labrie F: Reduced testosterone and adrenal C19 steroid levels in obese men. Metabolism. 1995 Apr;44(4):513-9. [PubMed:7723675 ]
  5. Vermeulen A, Deslypere JP: Intratesticular unconjugated steroids in elderly men. J Steroid Biochem. 1986 May;24(5):1079-83. [PubMed:2941625 ]
  6. Anderson DC, Child DF, Sutcliffe CH, Buckley CH, Davies D, Longson D: Cushing's syndrome, nodular adrenal hyperplasia and virilizing carcinoma. Clin Endocrinol (Oxf). 1978 Jul;9(1):1-14. [PubMed:209918 ]
  7. Dikkeschei LD, Wolthers BG, Willemse PH, van der Pol H, de Ruyter-Buitenhuis AW, Nagel GT: The determination of delta-5-androstenediol and its sulphate in serum and urine by gas chromatography-mass spectrometry. Clin Endocrinol (Oxf). 1993 Oct;39(4):469-74. [PubMed:8287574 ]
  8. Bonney RC, Reed MJ, Beranek PA, James VH: Metabolism of adrenal androgens by human endometrium and adrenal cortex. J Steroid Biochem. 1985 Sep;23(3):347-52. [PubMed:2995729 ]
  9. Mizokami A, Koh E, Fujita H, Maeda Y, Egawa M, Koshida K, Honma S, Keller ET, Namiki M: The adrenal androgen androstenediol is present in prostate cancer tissue after androgen deprivation therapy and activates mutated androgen receptor. Cancer Res. 2004 Jan 15;64(2):765-71. [PubMed:14744796 ]
  10. Higashi T, Takayama N, Shimada K: Enzymic conversion of 3beta-hydroxy-5-ene-steroids and their sulfates to 3-oxo-4-ene-steroids for increasing sensitivity in LC-APCI-MS. J Pharm Biomed Anal. 2005 Sep 15;39(3-4):718-23. [PubMed:15905063 ]
  11. Brown GA, Vukovich M, King DS: Testosterone prohormone supplements. Med Sci Sports Exerc. 2006 Aug;38(8):1451-61. [PubMed:16888459 ]
  12. Mendonca BB, Bloise W, Arnhold IJ, Batista MC, Toledo SP, Drummond MC, Nicolau W, Mattar E: Male pseudohermaphroditism due to nonsalt-losing 3 beta-hydroxysteroid dehydrogenase deficiency: gender role change and absence of gynecomastia at puberty. J Steroid Biochem. 1987 Dec;28(6):669-75. [PubMed:2826919 ]
  13. Brind JL: Direct radioimmunoassay of androstenediol-3-sulfate in the serum of normal men. Steroids. 1991 Jun;56(6):320-4. [PubMed:1926228 ]
  14. Jones DL, James VH: The identification, quantification and possible origin of non-polar conjugates in human plasma. J Steroid Biochem. 1985 Feb;22(2):243-7. [PubMed:3157025 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihydroxy-4-cholesten-3-one and 7-alpha-hydroxy-4-cholesten-3-one can also act as substrates.
Gene Name:
AKR1D1
Uniprot ID:
P51857
Molecular weight:
32889.38
General function:
Involved in 3-oxo-5-alpha-steroid 4-dehydrogenase activity
Specific function:
Converts testosterone into 5-alpha-dihydrotestosterone and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and androgen physiology.
Gene Name:
SRD5A1
Uniprot ID:
P18405
Molecular weight:
29458.18
General function:
Involved in oxidoreductase activity
Specific function:
Favors the reduction of androstenedione to testosterone. Uses NADPH while the two other EDH17B enzymes use NADH.
Gene Name:
HSD17B3
Uniprot ID:
P37058
Molecular weight:
34515.345
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular weight:
57882.48
General function:
Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:
3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids. Efficiently catalyzes the transformation of pregnenolone to progesterone, 17-alpha-hydroxypregnenolone to 17-alpha-hydroxyprogesterone, DHEA to 4-androstenedione, dihydrotestosterone to 5-alpha-androstane-3 beta,17 beta-diol, dehydroepiandrosterone to androstenedione and 5-alpha-androstan-3 beta,17 beta-diol to 5-alpha-dihydrotestosterone.
Gene Name:
HSD3B1
Uniprot ID:
P14060
Molecular weight:
42251.25
Reactions
Testosterone + Hydrogen Ion + NADH → 5-Androstenediol + NADdetails
General function:
Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:
3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids.
Gene Name:
HSD3B2
Uniprot ID:
P26439
Molecular weight:
42051.845
Reactions
Testosterone + Hydrogen Ion + NADH → 5-Androstenediol + NADdetails