Hmdb loader
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:00 UTC
HMDB IDHMDB0000352
Secondary Accession Numbers
  • HMDB00352
Metabolite Identification
Common Name16a-Hydroxydehydroisoandrosterone
Description16a-Hydroxydehydroisoandrosterone, also known as 3b,16a-dihydroxy-androst-5-en-17-one or 5-androstene-3beta,16alpha-diol-17-one, 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. Thus, 16a-hydroxydehydroisoandrosterone is considered to be a steroid lipid molecule. 16a-Hydroxydehydroisoandrosterone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1582752125
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-dehydroepiandrosteroneHMDB
3beta,16alpha-Dihydroxyandrost-5-en-17-oneHMDB
16 alpha-HydroxydehydroisoandrosteroneHMDB
3,16-Dihydroxyandrost-5-en-17-oneHMDB
3 beta,16 beta-Dihydroxyandrost-5-en-17-oneHMDB
16 beta-HydroxydehydroepiandrosteroneHMDB
3 beta,16 alpha-Dihydroxyandrost-5-en-17-oneHMDB
16-Hydroxydehydroepiandrosterone, (16beta)-isomerHMDB
16-Hydroxydehydroepiandrosterone, (3alpha,16alpha)-isomerHMDB
16Α-hydroxydehydroepiandrosteroneHMDB
16a-HydroxydehydroisoandrosteroneGenerator
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
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
  • 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
Disposition
Biological locationRoute of exposureSource
Process
Role
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 Solubility0.12 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
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]+172.62331661259
DarkChem[M-H]-167.52831661259
AllCCS[M+H]+177.89632859911
AllCCS[M-H]-180.47832859911
DeepCCS[M-2H]-208.22630932474
DeepCCS[M+Na]+182.49830932474
AllCCS[M+H]+177.932859911
AllCCS[M+H-H2O]+174.932859911
AllCCS[M+NH4]+180.732859911
AllCCS[M+Na]+181.532859911
AllCCS[M-H]-180.532859911
AllCCS[M+Na-2H]-180.632859911
AllCCS[M+HCOO]-180.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
16a-Hydroxydehydroisoandrosterone[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@]12C2709.5Standard polar33892256
16a-Hydroxydehydroisoandrosterone[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@]12C2602.5Standard non polar33892256
16a-Hydroxydehydroisoandrosterone[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@]12C2716.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
16a-Hydroxydehydroisoandrosterone,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]1C[C@@H](O[Si](C)(C)C)C2=O2802.3Semi standard non polar33892256
16a-Hydroxydehydroisoandrosterone,1TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1C[C@@H](O)C2=O2769.5Semi standard non polar33892256
16a-Hydroxydehydroisoandrosterone,1TMS,isomer #3C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]1CC(O)=C2O[Si](C)(C)C2759.1Semi standard non polar33892256
16a-Hydroxydehydroisoandrosterone,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1C[C@@H](O[Si](C)(C)C)C2=O2828.4Semi standard non polar33892256
16a-Hydroxydehydroisoandrosterone,2TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C2833.8Semi standard non polar33892256
16a-Hydroxydehydroisoandrosterone,2TMS,isomer #3C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC(O)=C2O[Si](C)(C)C2765.2Semi standard non polar33892256
16a-Hydroxydehydroisoandrosterone,3TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C2825.9Semi standard non polar33892256
16a-Hydroxydehydroisoandrosterone,3TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C2812.9Standard non polar33892256
16a-Hydroxydehydroisoandrosterone,3TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C3081.8Standard polar33892256
16a-Hydroxydehydroisoandrosterone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1C[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]2(C)C1=O3073.1Semi standard non polar33892256
16a-Hydroxydehydroisoandrosterone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4C[C@@H](O)C(=O)[C@@]4(C)CC[C@@H]32)C13042.6Semi standard non polar33892256
16a-Hydroxydehydroisoandrosterone,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=C(O)C[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C3042.9Semi standard non polar33892256
16a-Hydroxydehydroisoandrosterone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)[C@@]4(C)CC[C@@H]32)C13359.6Semi standard non polar33892256
16a-Hydroxydehydroisoandrosterone,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]2C13384.5Semi standard non polar33892256
16a-Hydroxydehydroisoandrosterone,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=C(O)C[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3308.8Semi standard non polar33892256
16a-Hydroxydehydroisoandrosterone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@]43C)[C@@H]2C13579.4Semi standard non polar33892256
16a-Hydroxydehydroisoandrosterone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@]43C)[C@@H]2C13382.3Standard non polar33892256
16a-Hydroxydehydroisoandrosterone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@]43C)[C@@H]2C13374.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 16a-Hydroxydehydroisoandrosterone GC-MS (Non-derivatized) - 70eV, Positivesplash10-01r2-0190000000-8f531134e0d23da25da52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16a-Hydroxydehydroisoandrosterone GC-MS (2 TMS) - 70eV, Positivesplash10-001i-1038900000-e6ab9b68f3f5cbbada202017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16a-Hydroxydehydroisoandrosterone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16a-Hydroxydehydroisoandrosterone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16a-Hydroxydehydroisoandrosterone GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16a-Hydroxydehydroisoandrosterone GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16a-Hydroxydehydroisoandrosterone GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16a-Hydroxydehydroisoandrosterone GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16a-Hydroxydehydroisoandrosterone GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16a-Hydroxydehydroisoandrosterone GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16a-Hydroxydehydroisoandrosterone GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16a-Hydroxydehydroisoandrosterone GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16a-Hydroxydehydroisoandrosterone GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16a-Hydroxydehydroisoandrosterone GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16a-Hydroxydehydroisoandrosterone GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16a-Hydroxydehydroisoandrosterone 10V, Positive-QTOFsplash10-052r-0194000000-ebe887790f49b46819232016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16a-Hydroxydehydroisoandrosterone 20V, Positive-QTOFsplash10-0a4r-0291000000-dd1067b167ad1b9420532016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16a-Hydroxydehydroisoandrosterone 40V, Positive-QTOFsplash10-0pxr-3690000000-ff802ceebc639b3e7c1f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16a-Hydroxydehydroisoandrosterone 10V, Negative-QTOFsplash10-0udi-0029000000-c31ccc892715a3b415702016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16a-Hydroxydehydroisoandrosterone 20V, Negative-QTOFsplash10-0udi-0079000000-ca33420930d851c47a692016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16a-Hydroxydehydroisoandrosterone 40V, Negative-QTOFsplash10-007c-1090000000-e8a494aec5ecf04bc8fd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16a-Hydroxydehydroisoandrosterone 10V, Positive-QTOFsplash10-0a4r-0069000000-057040f4b3850a0663672021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16a-Hydroxydehydroisoandrosterone 20V, Positive-QTOFsplash10-0670-0982000000-202e2a5dcedc0d7b97b12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16a-Hydroxydehydroisoandrosterone 40V, Positive-QTOFsplash10-0005-1910000000-6544390a129e44d961062021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16a-Hydroxydehydroisoandrosterone 10V, Negative-QTOFsplash10-0udi-0009000000-93986d59045cc7fce5512021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16a-Hydroxydehydroisoandrosterone 20V, Negative-QTOFsplash10-0udi-0039000000-af52444aa96638a90cb72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16a-Hydroxydehydroisoandrosterone 40V, Negative-QTOFsplash10-0uk9-1094000000-48ce674daa94d6aea6fb2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
UrineDetected and Quantified0.35 +/- 0.24 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDEANDRSTRN
MarkerDB IDNot Available
Good Scents IDNot Available
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