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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-25 18:31:02 UTC
HMDB IDHMDB0000352
Secondary Accession Numbers
  • HMDB00352
StatusDetected and Quantified
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:
Source:
Route of exposure:
Subcellular:
Enteral:
Biological:
Biofluid and excreta:
Animal:
Process
Naturally occurring process:
Biological process:
Cellular process:
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity86.15 m3·mol-1ChemAxon
Polarizability34.85 Å3ChemAxon
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-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
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
    NuGOwiki LinkHMDB0000352
    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