1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyl(4,4,5,6,6-2H5)tetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]ethan-1-one

• ChemBase ID: 159659
• Molecular Formular: C21H34O2
• Molecular Mass: 318.49346
• Monoisotopic Mass: 318.25588033
• SMILES: C1[C@H](C[C@H]2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@H](CC2)C(=O)C)C)C)O
• 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-dimethyl(4,4,5,6,6-^2H₅)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]ethan-1-one
• IUPAC Traditional name: 1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyl(4,4,5,6,6-^2H₅)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]ethanone
• Synonyms: (+)-3α-Hydroxy-5α-pregnan-20-one-d5; (3α,5α)-3-Hydroxypregnan-20-one-d5; 3α,5α-THP-d5; 3α,5α-Tetrahydroprogesterone-d5; 3α-Hydroxy-5α-dihydroprogesterone-d5; 3α-Hydroxy-5α-pregnan-20-one-d5; 3α-Hydroxy-5α-pregnane-20-one-d5; 5α-Pregnan-3α-ol-20-one-d5; 5α-Pregnane-3α-ol-20-one-d5; Allopregnan-3α-ol-20-one-d5; Allopregnanolone-d5; Allotetrahydroprogesterone-d5; (3α)-Allopregnanolone-d5

Database IDs

• PubChem SID: 162253794
• PubChem CID: 71313081

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

DETAILS

Toronto Research Chemicals - A547102

Labelled (3α)-Allopregnanolone. (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

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)