Basic Info

Common Name18-Hydroxycorticosterone(F05321)
2D Structure
Description

11 beta,18,21-Trihydroxypregn-4-ene-3,20-dione. 18-Hydroxycorticosterone is a derivative of corticosterone. It serves as an intermediate in the synthesis of aldosterone by the enzyme aldosterone synthase in the zona glomerulosa.

FRCD IDF05321
CAS Number561-65-9
PubChem CID11222
FormulaC21H30O5
IUPAC Name

(8S,9S,10R,11S,13R,14S,17S)-11-hydroxy-17-(2-hydroxyacetyl)-13-(hydroxymethyl)-10-methyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

InChI Key

HFSXHZZDNDGLQN-ZVIOFETBSA-N

InChI

InChI=1S/C21H30O5/c1-20-7-6-13(24)8-12(20)2-3-14-15-4-5-16(18(26)10-22)21(15,11-23)9-17(25)19(14)20/h8,14-17,19,22-23,25H,2-7,9-11H2,1H3/t14-,15-,16+,17-,19+,20-,21+/m0/s1

Canonical SMILES

CC12CCC(=O)C=C1CCC3C2C(CC4(C3CCC4C(=O)CO)CO)O

Isomeric SMILES

C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2[C@H](C[C@]4([C@H]3CC[C@@H]4C(=O)CO)CO)O

Wikipedia18-Hydroxycorticosterone
Synonyms
        
            4U5T0O9SI3
        
            11beta,18,21-trihydroxy-pregn-4-ene-3,20-dione
        
            18-HYDROXYCORTICOSTERONE
        
            561-65-9
        
            UNII-4U5T0O9SI3
        
            11beta,18,21-Trihydroxypregn-4-ene-3,20-dione
        
            EINECS 209-221-9
        
            AC1L1WVV
        
            18-hydroxy corticosterone
        
            SCHEMBL142427
        
Classifies
                

                  
                    Animal Toxin
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
SubclassHydroxysteroids
Intermediate Tree NodesNot available
Direct Parent21-hydroxysteroids
Alternative Parents
Molecular FrameworkAliphatic homopolycyclic compounds
SubstituentsProgestogin-skeleton - 21-hydroxysteroid - Pregnane-skeleton - 20-oxosteroid - 18-hydroxysteroid - 3-oxo-delta-4-steroid - 3-oxosteroid - 11-hydroxysteroid - 11-beta-hydroxysteroid - Oxosteroid - Delta-4-steroid - Cyclohexenone - Alpha-hydroxy ketone - Cyclic alcohol - Ketone - Secondary alcohol - Cyclic ketone - Hydrocarbon derivative - Organic oxide - Carbonyl group - Organic oxygen compound - Alcohol - Organooxygen compound - Primary alcohol - Aliphatic homopolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.

Properties

Property NameProperty Value
Molecular Weight362.466
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Complexity655
Monoisotopic Mass362.209
Exact Mass362.209
XLogP0.7
Formal Charge0
Heavy Atom Count26
Defined Atom Stereocenter Count7
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9095
Human Intestinal AbsorptionHIA+0.9945
Caco-2 PermeabilityCaco2+0.7004
P-glycoprotein SubstrateSubstrate0.8097
P-glycoprotein InhibitorNon-inhibitor0.6756
Non-inhibitor0.7694
Renal Organic Cation TransporterNon-inhibitor0.6677
Distribution
Subcellular localizationMitochondria0.8676
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8306
CYP450 2D6 SubstrateNon-substrate0.8901
CYP450 3A4 SubstrateSubstrate0.7030
CYP450 1A2 InhibitorNon-inhibitor0.9385
CYP450 2C9 InhibitorNon-inhibitor0.9170
CYP450 2D6 InhibitorNon-inhibitor0.9274
CYP450 2C19 InhibitorNon-inhibitor0.9132
CYP450 3A4 InhibitorNon-inhibitor0.9020
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9217
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9112
Inhibitor0.5274
AMES ToxicityNon AMES toxic0.8959
CarcinogensNon-carcinogens0.9568
Fish ToxicityHigh FHMT0.9906
Tetrahymena Pyriformis ToxicityHigh TPT0.9722
Honey Bee ToxicityHigh HBT0.7631
BiodegradationNot ready biodegradable0.9460
Acute Oral ToxicityIII0.6351
Carcinogenicity (Three-class)Non-required0.6457

Model Value Unit
Absorption
Aqueous solubility-3.8016LogS
Caco-2 Permeability0.8456LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.6255LD50, mol/kg
Fish Toxicity1.1443pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.8752pIGC50, ug/L

Targets

General Function:
Zinc ion binding
Specific Function:
Receptor for both mineralocorticoids (MC) such as aldosterone and glucocorticoids (GC) such as corticosterone or cortisol. Binds to mineralocorticoid response elements (MRE) and transactivates target genes. The effect of MC is to increase ion and water transport and thus raise extracellular fluid volume and blood pressure and lower potassium levels.
Gene Name:
NR3C2
Uniprot ID:
P08235
Molecular Weight:
107066.575 Da