1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]ethan-1-one

• ChemBase ID: 106017
• Molecular Formular: C21H34O2
• Molecular Mass: 318.49346
• Monoisotopic Mass: 318.25588033
• SMILES: O=C(C)[C@@H]1[C@]2(CC[C@H]3[C@H]([C@@H]2CC1)CC[C@H]1C[C@H](O)CC[C@]31C)C
• Canonical SMILES: O[C@@H]1CC[C@]2([C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2C(=O)C)C)C
• 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
• InChIKey: AURFZBICLPNKBZ-SYBPFIFISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]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]ethan-1-one
• IUPAC Traditional name: 3a-hydroxy-5a-pregnan-20-one; 3α-hydroxy-5α-pregnan-20-one
• Synonyms: 3α-Hydroxy-5α-pregnan-20-one; 3α-OH-DHP; Allopregnan-3α-ol-20-one; Allopregnanolone; 5α-Pregnan-3α-ol-20-one; Allopregnan-3α-ol-20-one; 3α-Hydroxy-5α-20-one; ALLOPREGNANOLONE; (+)-3α-Hydroxy-5α-pregnan-20-one; (3α,5α)-3-Hydroxypregnan-20-one; 3α,5α-THP; 3α,5α-Tetrahydroprogesterone; 3α-Hydroxy-5α-dihydroprogesterone; 3α-Hydroxy-5α-pregnane-20-one; 5α-Pregnan-3α-ol-20-one; 5α-Pregnane-3α-ol-20-one; Allotetrahydroprogesterone; (3α)-Allopregnanolone

Database IDs

• CAS Number: 516-54-1
• MDL Number: MFCD00003677
• Beilstein Number: 3211363
• PubChem SID: 24278659; 162089001
• PubChem CID: 92786

CALCULATED PROPERTIES

• Acid pKa: 18.296396
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.986938
• LogD (pH = 7.4): 3.986938
• Log P: 3.986938
• Molar Refractivity: 92.9067 cm^3
• Polarizability: 37.18642 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: chloroform: soluble20 mg/mL, clear, colorless; DMSO: soluble5 mg/mL; methanol: soluble
• Apperance: white solid

Safety Information

• Storage Condition: Room Temperature (15-30°C), Protect from light, Avoid excess heat
• RTECS: TU4383000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... GABRA1(2554), GABRA2(2555), GABRA3(2556), GABRA4(2557), GABRA5(2558), GABRA6(2559), GABRB1(2560), GABRB2(2561), GABRB3(2562)mouse ... Gabrg2(14406)rat ... Gabra1(29705), Gabra2(29706), Gabrg2(29709)

Product Information

• Purity: ≥95%; ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C21H34O2

DETAILS

MP Biomedicals - 02195886

Purity: >95%
A neurosteroid with potent ligand properties against GABA Type A receptor complexes in mammalian CNS potentiating the GABA receptor-mediated chloride uptake in synaptoneurosomes.

Sigma Aldrich - P8887

Biochem/physiol Actions
Positive allosteric modulator of GABAA chloride channel.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. P8887.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - A547100

(3α)-Allopregnanolone acts as a GABAA receptor positive allosteric modulator. (3α)-Allopregnanolone is a metabolite of Progesterone (P755900). (3α)-Allopregnanolone is a neuroactive steroid present in the blood and also the brain.

REFERENCES

• Puja, G. et al.: Neuron, 4, 759 (1990)
• Belelli, D. et ael. Neurosteroid, 6, 565 (1990)
• Viapiano, M. et al.: Neurochem. Res., 23, 155 (1990)