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

• ChemBase ID: 2503
• Molecular Formular: C21H32O2
• Molecular Mass: 316.47758
• Monoisotopic Mass: 316.24023026
• SMILES: C1C[C@H](O)CC2=CC[C@@H]3[C@@H]([C@@]12C)CC[C@]1([C@H]3CC[C@@H]1C(=O)C)C
• Canonical SMILES: O[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2C(=O)C)C)C1)C
• InChI: InChI=1S/C21H32O2/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/h4,15-19,23H,5-12H2,1-3H3/t15-,16-,17+,18-,19-,20-,21+/m0/s1
• InChIKey: ORNBQBCIOKFOEO-QGVNFLHTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(1S,2R,5S,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-14-yl]ethan-1-one; 1-[(1S,2R,5S,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one
• IUPAC Traditional name: pregnenolone
• Synonyms: 1-((3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone; 3-Hydroxypregn-5-en-20-one; Pregnenolone; Pregnenolone; 3β-Hydroxy-5-pregnen-20-one; Pregnenolone; 5-Pregnen-3β-ol-20-one; (3β)-3-Hydroxy-pregn-5-en-20-one; (3β)-3-Hydroxypregn-5-en-20-one; 5-Pregnenolone; Arthenolone; Bina-Skin; Enelone; NSC 1616; Pregnolon; Prenolon; Regnosone; Skinostelon

Database IDs

• CAS Number: 145-13-1
• EC Number: 205-647-4
• MDL Number: MFCD00003628
• Beilstein Number: 2059026
• PubChem SID: 46506718; 24887880; 160965953; 24899008
• PubChem CID: 8955

CALCULATED PROPERTIES

JChem

• Acid pKa: 18.20429
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.5813584
• LogD (pH = 7.4): 3.5813584
• Log P: 3.5813584
• Molar Refractivity: 93.7567 cm^3
• Polarizability: 36.94731 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.06
• LOG S: -4.37
• Solubility (Water): 1.36e-02 g/l

PROPERTIES

Physical Property

• Solubility: Chlorform; Ethanol
• Apperance: Cryst.; White Solid
• Melting Point: 174-177°C; 188-190 °C
• Optical Rotation: [α]20/D +27±1°, c = 1% in ethanol

Safety Information

• Storage Condition: -20°C; Refrigerator
• RTECS: TU5560700
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Target: Estrogen receptor
• Gene Information: human ... SERPINA6(866)rat ... Ar(24208)

Product Information

• Purity: ≥98%
• Grade: purum
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C21H32O2

DETAILS

DrugBank - DB02789

• Drug Groups: experimental
• Description: A 21-carbon steroid, derived from CHOLESTEROL and found in steroid hormone-producing tissues. Pregnenolone is the precursor to GONADAL STEROID HORMONES and the adrenal CORTICOSTEROIDS. [PubChem]

Selleck Chemicals - S1914

Biological Activity:

Sigma Aldrich - P9129

Biochem/physiol Actions
One of a small number of "neurosteroids," steroids synthesized in the brain rather than peripheral sources. Decreased levels of these neurosteroids has been implicated in rodent cognitive decline with age, but studies in humans have been contradictory.1
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. P9129.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 81630

Biochem/physiol Actions
One of a small number of "neurosteroids," steroids synthesized in the brain rather than peripheral sources. Decreased levels of these neurosteroids has been implicated in rodent cognitive decline with age, but studies in humans have been contradictory.1

Toronto Research Chemicals - P712200

Pregnenolone is a steroid hormone involved in the steroidogenesis of progesterone, mineralocorticoids, glucocorticoids, androgens, and estrogens. As such it is a prohormone. Pregnenolone is a GABAA antagonist and increases neurogenesis in the hippocampus.

REFERENCES

• Geick, A., et al.: J. Biol. Chem., 276, 14581 (1976)
• Johnson, D., et al.: Toxicol. Sci., 66, 16 (1976)
• Abe, C., et al.: Lipids, 42, 637 (1976)
• Bjondahl, K., et al.: Med. Biol., 54, 454 (1976)