Common Name3alpha-hydroxy-5alpha-pregnan-20-one
DescriptionAllopregnanolone is 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.
Structure
Molecular FormulaC21H34O2
Average Mass318.49350
Monoisotopic Mass318.25588
IUPAC Name1-[(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
Traditional NameAllopregnan-3α-ol-20-one
CAS Registry Number516-54-1
SMILESCC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
InChI IdentifierInChI=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
InChI KeyAURFZBICLPNKBZ-SYBPFIFISA-N
CHEBI IDCHEBI:50169
HMDB IDHMDB0001449
StateNot Available
Water Solubility1.36e-03 g/l
logP4.28
logS-5.37
pKa (Strongest Acidic)18.30
pKa (Strongest Basic)-1.36
Hydrogen Acceptor Count2
Hydrogen Donor Count1
Polar Surface Area37.3 Ų
Rotatable Bond Count1
Physiological Charge0
Formal Charge0
Refractivity92.91 m³·mol⁻¹
Polarizability38.57

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