| Common Name |
16a-Hydroxydehydroisoandrosterone
| Description |
16a-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 slifatase deficiency (PSD), a rare disorder with low estrogen production due to placental enzymatic deficiency. (PMID 2150812 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
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 Formlia |
C19H28O3
| Average Molecliar Weight |
304.4238
| Monoisotopic Molecliar Weight |
304.203844762
| 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 Name |
16a-Hydroxy-DHEA
| CAS Registry Number |
1232-73-1
| 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 Key |
QQIVKFZWLZJXJT-DNKQKWOHSA-N
| Chemical Taxonomy |
| Classification |
Not classified
| Ontology |
| Status |
Detected and 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 Emlisifiers
| Cellliar locations |
Extracellliar
Membrane (predicted from logP)
Endoplasmic reticlium
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
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
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Extracellliar
Membrane (predicted from logP)
Endoplasmic reticlium
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodExpected but not Quantified Not AvailableNot Available
Normal
details
UrineDetected and Quantified0.35 +/- 0.24 umol/mmol creatinineAdlit (>18 years old)FemaleNormal
14643447
details
|
| Abnormal Concentrations |
|
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
UrineDetected and Quantified0.35 +/- 0.21 umol/mmol creatinineAdlit (>18 years old)FemaleThyroid cancer
14643447
details
| Associated Disorders and Diseases |
| Disease References |
| Thyroid cancer |
- 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 IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB021975
| KNApSAcK ID |
Not Available
| Chemspider ID |
92168
| KEGG Compound ID |
C05139
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00352
| Metagene Link |
HMDB00352
| METLIN ID |
5341
| PubChem Compound |
102030
| PDB ID |
Not Available
| ChEBI ID |
27771
Product: AZD9056 (hydrochloride)
References |
| Synthesis Reference |
Siiter, 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 |
- 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 (authors transl)]. Nihon Sanka Fujinka Gakkai Zasshi. 1982 Mar;34(3):325-34. [PubMed:6461703 ]
- 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 + NAD |
details |
- 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 + NAD |
details |
PMID: 19777062