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Record Information
Version3.6
Creation Date2006-08-13 05:18:00 UTC
Update Date2013-05-21 21:53:36 UTC
HMDB IDHMDB03818
Secondary Accession NumbersNone
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
Thumb
Synonyms
  1. 3beta,17beta-Dihydroxy-5-androstene
  2. 3beta,17beta-Dihydroxyandrost-5-ene
  3. 5-Androstenediol
  4. Androst-5-ene-3,17-diol
  5. Androst-5-ene-3b,17b-diol
  6. Androst-5-ene-3beta,17beta-diol
  7. Androst-5-enediol
  8. Androstenediol
  9. b,17b-Diol
  10. delta(Sup 5)-Androstenediol
  11. delta-5-Androstenediol
  12. Delta5-Androstenediol
  13. Hermaphrodiol
  14. Tetrabol
Chemical FormulaC19H30O2
Average Molecular Weight290.4403
Monoisotopic Molecular Weight290.224580204
IUPAC Name(1S,2R,5S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,14-diol
Traditional IUPAC Nameandrostenediol
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
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassAndrogens and Derivatives
Other Descriptors
  • 17beta-hydroxy steroid(ChEBI)
  • 3beta-hydroxy steroid(ChEBI)
  • Aliphatic Homopolycyclic Compounds
  • Androstane and derivatives(KEGG)
  • C19 steroids (androgens) and derivatives(KEGG)
  • C19 steroids (androgens) and derivatives(Lipidmaps)
  • Hydroxysteroids
  • androgen(ChEBI)
Substituents
  • Bicyclohexane
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Secondary Alcohol
  • Sesquiterpene Backbone
Direct ParentAndrogens and Derivatives
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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 Area40.46ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity85.48ChemAxon
Polarizability34.68ChemAxon
Spectra
SpectraGC-MS
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue Location
  • Adipose Tissue
  • Adrenal Cortex
  • Muscle
  • Prostate
  • Testes
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023228
KNApSAcK IDNot Available
Chemspider ID10188
KEGG Compound IDC04295
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAndrostenediol
NuGOwiki LinkHMDB03818
Metagene LinkHMDB03818
METLIN ID6983
PubChem Compound10634
PDB IDB81
ChEBI ID2710
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