| Common Name |
3b,16a-Dihydroxyandrostenone slifate
| Description |
3b,16a-Dihydroxyandrostenone slifate (DHEAS) is a normal human metabolite identified in pregnant women in placenta, in breast milk, and the size of the neonates adrenal glands is in direct relation to the levels of DHEAS in pregnancy. (PMIDs 2963083, 2974194, 6216072, 6220027, 6220952, 6445373).
| Structure |
| Synonyms |
| Value |
Source |
16a-Hydroxydehydroepiandrosterone 3-slifateHMDB
16a-Hydroxydehydroepiandrosterone 3-sliphateHMDB
16a-Hydroxydehydroisoandrosterone slifateHMDB
16a-Hydroxydehydroisoandrosterone sliphateHMDB
3b,16a-Dihydroxy-5-androsten-17-one 3-slifateHMDB
3b,16a-Dihydroxy-5-androsten-17-one 3-sliphateHMDB
3b,16a-Dihydroxy-androstenone slifateHMDB
3b,16a-Dihydroxy-androstenone sliphateHMDB
3b,16a-Dihydroxyandrostenone sliphateHMDB
| Chemical Formlia |
C19H28O6S
| Average Molecliar Weight |
384.487
| Monoisotopic Molecliar Weight |
384.160659318
| IUPAC Name |
[(1S,2S,10S,11S,13R,15R)-5-hydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-13-yl]oxidaneslifonic acid
| Traditional Name |
[(1S,2S,10S,11S,13R,15R)-5-hydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-13-yl]oxidaneslifonic acid
| CAS Registry Number |
4873-65-8
| SMILES |
[H][C@@]12C[C@H](C[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)=CC(=O)[C@]12C)OS(O)(=O)=O
| InChI Identifier |
InChI=1S/C19H28O6S/c1-18-6-5-15-14(16(18)9-13(10-18)25-26(22,23)24)4-3-11-7-12(20)8-17(21)19(11,15)2/h8,11,13-16,20H,3-7,9-10H2,1-2H3,(H,22,23,24)/t11?,13-,14-,15+,16+,18-,19+/m1/s1
| InChI Key |
AWUIWQRSWWITFQ-LZRZFMTJSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as slifated steroids. These are sterol lipids containing a slifate group attached to the steroid skeleton.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Lipids and lipid-like moleclies
| Sub Class |
Steroids and steroid derivatives
| Direct Parent |
Slifated steroids
| Alternative Parents |
Androgens and derivatives
Oxosteroids
3-hydroxysteroids
Cyclohexenones
Slifuric acid monoesters
Alkyl slifates
Vinylogous acids
Enols
Organic oxides
Hydrocarbon derivatives
| Substituents |
Slifated steroid skeleton
Androgen-skeleton
Androstane-skeleton
3-hydroxysteroid
Hydroxysteroid
1-oxosteroid
Oxosteroid
Cyclohexenone
Slifuric acid ester
Alkyl slifate
Slifate-ester
Slifuric acid monoester
Organic slifuric acid or derivatives
Vinylogous acid
Ketone
Enol
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aliphatic homopolycyclic compound
| Molecliar Framework |
Aliphatic homopolycyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Expected but 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 Emlisifiers
| Cellliar locations |
Cytoplasm
Extracellliar
Membrane (predicted from logP)
| 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 Solubility0.046 mg/mLALOGPS
logP-0.08ALOGPS
logP2.99ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)-1.4ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area100.9 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity96.94 m3·mol-1ChemAxon
Polarizability40.66 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
Extracellliar
Membrane (predicted from logP)
| Biofluid Locations |
Not Available
| Tissue Location |
Kidney
Liver
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| 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 |
FDB022004
| KNApSAcK ID |
Not Available
| Chemspider ID |
17215945
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00386
| Metagene Link |
HMDB00386
| METLIN ID |
5375
| PubChem Compound |
Not Available
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: Beaucage reagent
References |
| Synthesis Reference |
Easterling, William E., Jr.; Simmer, Hans H.; Dignam, William J.; Frankland, Marjorie V.; Naftolin, Frederick. Neutral C19 steroids and steroid sulfates in human pregnancy. II. Dehydroepiandrosterone sulfate, 16a-hydroxydehydroepiandrosterone, and 16a-hydroxydehydroepiandrosterone sulfate in maternal and fetal blood of pregnancies with anencephalic and normal fetuses. Steroids (1966), 8(2), 157-78. |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Smith JL, Lewindon PJ, Hoskins AC, Pereira TN, Setchell KD, OConnell NC, Shepherd RW, Ramm GA: Endogenous ursodeoxycholic acid and cholic acid in liver disease due to cystic fibrosis. Hepatology. 2004 Jun;39(6):1673-82. [PubMed:15185309 ]
|
PMID: 23512340