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Structure Database (LMSD)

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Common Name

3beta-hydroxy-5beta-pregnan-20-one

Systematic Name

3β-hydroxy-5β-pregnan-20-one

Synonyms

(3beta,5beta)-3-hydroxypregnan-20-one
3beta-Hydroxy-5beta-pregnane-20-one
3beta-hydroxy-5beta-pregnane-20-one
3beta-hydroxy-5beta-tetrahydroprogesterone
epipregnanolone

LM ID

LMST02030185

Formula

C₂₁H₃₄O₂

Exact Mass

Calculate m/z

318.25588

Sum Composition

ST 21:1;O2

Status

Curated

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Classification

Biological Context

Epipregnanolone is a neurosteroid and an active metabolite of the steroid hormone pregnenolone .¹ It is enzymatically formed from pregnenolone via the intermediates progesterone and 5β-dihydroprogesterone in the placenta.² Epipregnanolone inhibits spontaneous contractions in myometrial strips isolated from at-term pregnant women (IC50 = 156 µM).³ Epipregnanolone (10 and 20 mg/kg) decreases operant alcohol self-administration in rats.⁴ Maternal plasma levels of epipregnanolone increase over the duration of pregnancy.

This information has been provided by Cayman Chemical

References

1. Prince, R.J., and Simmonds, M.A. 5β-pregnan-3β-ol-20-one, a specific antagonist at the neurosteroid site of the GABAA receptor-complex. Neurosci. Lett. 135(2), 273-275 (1992).

2. Hill, M., Cibula, D., Havlíkova, H., et al. Circulating levels of pregnanolone isomers during the third trimester of human pregnancy. J. Steroid Biochem. Mol. Biol. 105(1-5), 166-175 (2007).

3. Perusquía, M., and Jasso-Kamel, J. Influence of 5α- and 5β-reduced progestins on the contractility of isolated human myometrium at term. Life Sci. 68(26), 2933-2944 (2001).

4. O'Dell, L.E., Purdy, R.H., Covey, D.F., et al. Epipregnanolone and a novel synthetic neuroactive steroid reduce alcohol self-administration in rats. Pharmacol. Biochem. Behav. 81(3), 543-550 (2005).

String Representations

InChiKey (Click to copy)

AURFZBICLPNKBZ-GRWISUQFSA-N

InChi (Click to copy)

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-/m1/s1

SMILES (Click to copy)

C1C[C@H](O)C[C@@]2([H])CC[C@]3([H])[C@@]([H])([C@]21C)CC[C@]1(C)[C@@]([H])(C(=O)C)CC[C@]13[H]