1.0 2011-09-21 00:17:07 UTC 2015-07-21 06:57:17 UTC FDB022630 Allopregnanolone A neuroactive metabolite of progesterone and a barbiturate-like modulator of central gamma-aminobutyric acid receptors that modify a range of behaviors, including the stress response. is a steroid created in the body when progesterone, the female sex hormone, is metabolized. Typically, THP (allopregnanolone) is released in the brain in response to stress, and quiets the neural system within 30 minutes of escalation. This steroid hormone has recently been found to be responsible for the extreme mood swings found in teenagers. In adults and pre-pubescent chlidren THP normally helps soothe the activity of brain cells by binding to GABA receptors that inhibit accelerating electrical activity. However, in pubescent teenagers THP actually becomes a GABA receptor antagonist. GABA (gamma-aminobutyric acid) is the primary inhibitory neurotransmitter in the brain with most sedatives (tranquilizers, anesthetics and alcohol) acting on the GABA receptor. [HMDB] (+)-3a-Hydroxy-5a-pregnan-20-one (3a,5a)-3-Hydroxypregnan-20-one (3a)-Allopregnanolone (3alpha,5alpha)-3-Hydroxypregnan-20-one (3α,5α)-3-hydroxypregnan-20-one 3-a-tetrahydroprogesterone 3-alpha-tetrahydroprogesterone 3a-Hydroxy-5a-dihydroprogesterone 3a-Hydroxy-5a-pregnan-20-one 3a-Hydroxy-5a-pregnane-20-one 3a-OH DHP 3a,5a-Pregnanolone 3a,5a-Tetrahydroprogesterone 3a,5a-THP 3alpha-OH DHP 3α-OH dhp 5a-Pregnan-3a-ol-20-one 5a-Pregnane-3a-ol-20-one Allopregnan-3a-ol-20-one Allopregnan-3alpha-ol-20-one Allopregnan-3α-ol-20-one Allotetrahydroprogesterone C21H34O2 318.4935 318.255880332 1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethan-1-one 1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethanone 516-54-1 [H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C InChI=1S/C21H34O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19,23H,4-12H2,1-3H3/t14-,15+,16-,17+,18-,19-,20-,21+/m0/s1 AURFZBICLPNKBZ-SYBPFIFISA-N belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. Gluco/mineralocorticoids, progestogins and derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Pregnane steroids Aliphatic homopolycyclic compounds 20-oxosteroids 3-alpha-hydroxysteroids Cyclic alcohols and derivatives Hydrocarbon derivatives Ketones Organic oxides Secondary alcohols 20-oxosteroid 3-alpha-hydroxysteroid 3-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Carbonyl group Cyclic alcohol Hydrocarbon derivative Hydroxysteroid Ketone Organic oxide Organic oxygen compound Organooxygen compound Oxosteroid Progestogin-skeleton Secondary alcohol 3-hydroxy-5alpha-pregnan-20-one C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives Solid logp 4.28 ALOGPS logs -5.37 ALOGPS solubility 1.36e-03 g/l ALOGPS logp 3.99 ChemAxon pka_strongest_acidic 18.3 ChemAxon pka_strongest_basic -1.4 ChemAxon iupac 1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethan-1-one ChemAxon average_mass 318.4935 ChemAxon mono_mass 318.255880332 ChemAxon smiles [H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C ChemAxon formula C21H34O2 ChemAxon inchi InChI=1S/C21H34O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19,23H,4-12H2,1-3H3/t14-,15+,16-,17+,18-,19-,20-,21+/m0/s1 ChemAxon inchikey AURFZBICLPNKBZ-SYBPFIFISA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 92.91 ChemAxon polarizability 38.52 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 2131 Specdb::CMs 13671 Specdb::CMs 31335 Specdb::CMs 38078 Specdb::CMs 148713 Specdb::MsMs 105369 Specdb::MsMs 105370 Specdb::MsMs 105371 Specdb::MsMs 171846 Specdb::MsMs 171847 Specdb::MsMs 171848 Specdb::MsMs 2706107 Specdb::MsMs 2706108 Specdb::MsMs 2706109 Specdb::MsMs 2999182 Specdb::MsMs 2999183 Specdb::MsMs 2999184 HMDB01449 32924 #<Reference:0x000055ce320eefd8> #<Reference:0x000055ce320eee20> #<Reference:0x000055ce320eec68> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823