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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 17:21:38 UTC
HMDB IDHMDB0000352
Secondary Accession Numbers
  • HMDB00352
Metabolite Identification
Common Name16a-Hydroxydehydroisoandrosterone
Description16a-Hydroxydehydroisoandrosterone is a metabolite present during pregnancy with increased concentrations as it progresses (PMID 6461703 ). A reduced level of 16a-Hydroxydehydroisoandrosterone is observed in cases of Placental sulfatase deficiency (PSD), a rare disorder with low estrogen production due to placental enzymatic deficiency. (PMID 2150812 ).
Structure
Thumb
Synonyms
ValueSource
16alpha-HydroxydehydroisoandrosteroneChEBI
3beta,16alpha-Dihydroxy-androst-5-en-17-oneChEBI
5-Androstene-3beta,16alpha-diol-17-oneChEBI
16α-hydroxydehydroisoandrosteroneGenerator
3b,16a-Dihydroxy-androst-5-en-17-oneGenerator
3β,16α-dihydroxy-androst-5-en-17-oneGenerator
5-Androstene-3b,16a-diol-17-oneGenerator
5-Androstene-3β,16α-diol-17-oneGenerator
16 alpha-Hydroxy-dehydroepiandrosteroneHMDB
16-HydroxydehydroandrosteroneHMDB
16-HydroxydehydroepiandrosteroneHMDB
16a-Hydroxy-dheaHMDB
16a-HydroxydehydroandrosteroneHMDB
16a-HydroxydehydroepiandrosteroneHMDB
3b,16a-Dihydroxyandrost-5-en-17-oneHMDB
Androst-5-ene-3b-16a-diol-17-oneHMDB
16alpha-Hydroxy-dehydroepiandrosteroneMeSH
3beta,16alpha-Dihydroxyandrost-5-en-17-oneMeSH
16 alpha-HydroxydehydroisoandrosteroneMeSH
3,16-Dihydroxyandrost-5-en-17-oneMeSH
3 beta,16 beta-Dihydroxyandrost-5-en-17-oneMeSH
16 beta-HydroxydehydroepiandrosteroneMeSH
3 beta,16 alpha-Dihydroxyandrost-5-en-17-oneMeSH
16-Hydroxydehydroepiandrosterone, (16beta)-isomerMeSH
16-Hydroxydehydroepiandrosterone, (3alpha,16alpha)-isomerMeSH
Chemical FormulaC19H28O3
Average Molecular Weight304.4238
Monoisotopic Molecular Weight304.203844762
IUPAC Name(1S,2R,5S,10R,11S,13R,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-one
Traditional Name16a-Hydroxy-DHEA
CAS Registry Number1232-73-1
SMILES
[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-16,20-21H,4-10H2,1-2H3/t12-,13+,14-,15-,16+,18-,19-/m0/s1
InChI KeyQQIVKFZWLZJXJT-DNKQKWOHSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 16-hydroxysteroid
  • 16-alpha-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Oxosteroid
  • 17-oxosteroid
  • Hydroxysteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

  Health condition:

    Cancer:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    System process:

Role

Industrial application:

Biological role:

  Molecular messenger:

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 Solubility0.12 g/LALOGPS
logP2.42ALOGPS
logP2.49ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)13.38ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity86.15 m³·mol⁻¹ChemAxon
Polarizability34.85 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01r2-0190000000-8f531134e0d23da25da5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001i-1038900000-e6ab9b68f3f5cbbada20View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0194000000-ebe887790f49b4681923View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0291000000-dd1067b167ad1b942053View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pxr-3690000000-ff802ceebc639b3e7c1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0029000000-c31ccc892715a3b41570View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0079000000-ca33420930d851c47a69View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007c-1090000000-e8a494aec5ecf04bc8fdView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified0.35 +/- 0.24 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    UrineDetected and Quantified0.35 +/- 0.21 umol/mmol creatinineAdult (>18 years old)FemaleThyroid cancer details
    Associated Disorders and Diseases
    Disease References
    Thyroid cancer
    1. Kim KM, Jung BH, Lho DS, Chung WY, Paeng KJ, Chung BC: Alteration of urinary profiles of endogenous steroids and polyunsaturated fatty acids in thyroid cancer. Cancer Lett. 2003 Dec 30;202(2):173-9. [PubMed:14643447 ]
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB021975
    KNApSAcK IDNot Available
    Chemspider ID92168
    KEGG Compound IDC05139
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN ID5341
    PubChem Compound102030
    PDB IDNot Available
    ChEBI ID27771
    References
    Synthesis ReferenceSiiter, Pentti K.; MacDonald, Paul C. Placental estrogen biosynthesis during human pregnancy. Journal of Clinical Endocrinology and Metabolism (1966), 26(7), 751-61.
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. Gothoda Y, Hirato K, Yanaihara T, Nakayama T, Kanbegawa A: [A study of 16 alpha OH-DHA and 16 alpha OH-pregnenolone in feto-placental unit (author's transl)]. Nihon Sanka Fujinka Gakkai Zasshi. 1982 Mar;34(3):325-34. [PubMed:6461703 ]
    2. Hirato K, Yanaihara T: Serum steroid hormone levels in neonates born from the mother with placental sulfatase deficiency. Endocrinol Jpn. 1990 Oct;37(5):731-9. [PubMed:2150812 ]

    Enzymes

    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
    16a-Hydroxyandrost-4-ene-3,17-dione + Hydrogen Ion + NADH → 16a-Hydroxydehydroisoandrosterone + 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
    16a-Hydroxyandrost-4-ene-3,17-dione + Hydrogen Ion + NADH → 16a-Hydroxydehydroisoandrosterone + NADdetails