Basic information
- Standard SMILES
CC(=O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C- InChIKey
ORNBQBCIOKFOEO-QGVNFLHTSA-N- Molecular formula
- C21H32O2
- Average molar mass
- 316.5 g/mol
- Monoisotopic mass
- 316.24023026
Overview
Pregnenolone is a 20-oxo steroid that is pregn-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 20. It has a role as a mouse metabolite and a human metabolite. It is a 3beta-hydroxy-Delta(5)-steroid, a 20-oxo steroid and a C21-steroid. It derives from a hydride of a pregnane.
Names & identifiers
- Preferred name
- Pregnenolone
- IUPAC
- 1-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
- English name
- Pregnenolone
- Molecular formula
- C21H32O2
- Molecular weight
- 316.48
Names & synonyms
Show more names
Database identifiers
- CAS
145-13-1- PubChem CID
- 8955
- DTXSID
DTXSID1036541- ChEMBL
CHEMBL253363- ChEBI
CHEBI:16581- UNII
- 73R90F7MQ8
- EC Number
- 205-647-4
- Nikkaji
- J11.381F
Properties
Computed structural properties
- XLogP
- 4.2
- Topological polar surface area
- 37.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 550
Experimental & physicochemical properties
LogP
4.22
4.22
Collision Cross Section
172.95 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
177.25 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]
174 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
214.8 Ų [M+Na]+
Physicochemical properties
- Melting point
- 188 · 188-190 °C
- alpha
- 28.5 · 28.5 º (c=1, EtOH)
- Boiling point
- 395.89 °C · 395.89°C (rough estimate)
- Density
- 1.0382 · 1.0382 (rough estimate)
- vapor pressure
- 0 · 0-0Pa at 20-25℃
- refractive index
- 1.5344 · 1.5344 (estimate)
- Flash point
- 9 ℃ · 9℃
- storage temp.
- Refrigerator
- solubility
- 10 mg/mL, · ethanol: soluble10mg/mL, clear, colorless to faintly yellow
- form
- Powder
- pka
- 15 · 15.00±0.70(Predicted)
- color
- White to off-white
- Water Solubility
- 41 mg/L · 41mg/L(room temperature)
- Merck
- 7733 · 7733
- BRN
- 2059026 · 2059026
- Major Application
- clinical testingclinical testing
- 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
- SMILES
- O[C@H]1CC[C@@]2([C@@H]3[C@H]([C@H]4[C@@]([C@H](CC4)C(=O)C)(CC3)C)CC=C2C1)C
- LogP
- 4.4 at · 4.4 at 20℃
- CAS DataBase Reference
- 145 · 145-13-1(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 73 R90F7MQ8 · 73R90F7MQ8
- NCI Drug Dictionary
- pregnenolone
- NIST Chemistry Reference
- Pregnenolone(145-13-1)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 2 · GHS02,GHS07
- Signal word
- Danger
- Hazard statements
- 225 · H225-H302+H312+H332-H319
- Precautionary statements
- 210 · P210-P280-P305+P351+P338
- Safety Statements
- 22 · 22-24/25
- RIDADR
- 1648 · UN 1648 3 / PGII
- WGK Germany
- 3 · 3
- RTECS
- 5560700 · TU5560700
- HS Code
- 29372900 · 29372900
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 13% (3 of 23) of reports.
Warning
H302 (87%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 23 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Safety data
- wgk
- 3
- rtecs
- TU5560700
- ridadr
- UN 1648 3 / PGII
- hs_code
- 29372900
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07
- safety_code
- 22-24/25
- Storage Class
- 3 - Flammable liquids
- Hazard statements
- H225-H302+H312+H332-H319
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2
- Precautionary statements
- P210-P280-P305+P351+P338
Chemistry & industry
Pharmacology
Metabolism/Metabolites
Pregnenolone has known human metabolites that include 1-(3,16-Dihydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone, Pregn-5-en-20-on-3b-yl sulfurate, and 2-Hydroxy-1-(3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone.
Applications
DescriptionPregnenolone serves as the common precursor in the formation of the adrenocorticoids and other steroid hormones. This C21 steroid is converted via enzymatic oxidations and isomerization of the double bond to a number of physiologically active C21 steroids, including the female sex hormone progesterone and the adrenocorticoids hydrocortisone (cortisol), corticosterone, and aldosterone. Oxidative cleavage of the two-carbon side chain of pregnenolone and subsequent enzymatic oxidations and isomerization lead to C19 steroids, including the androgens testosterone and dihydrotestosterone. The final group of steroids, the C18 female sex hormones, are derived from oxidative aromatization of the A ring of androgens to produce estrogens.
DescriptionPregnenolone is a natural steroid hormone that serves as a precursor for a wide range of steroids, including mineralocorticoids, glucocorticoids, androgens, and estrogens. Pregnenolone sulfate modulates NMDA receptor responses to exogenously applied glutamate and stimulates transient receptor potential melastatin 3 (TRPM3).
Usesglucocortcoid, antiinflammatory
UsesPregnenolone 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 an tagonist and increases neurogenesis in the hippocampus. It is a modulator of cytochrome P 450-3A
General DescriptionPregnenolone is an endogenous steroid hormone involved in the biological synthesis of other hormones. Pregnenolone is monitored as an ancillary test for congenital adrenal hyperplasia (CAH), particularly in situations where diagnosis of 21-hydroxylase and 11-hydroxylase deficiency has been ruled out. This Certified Spiking Solution is suitable for use in LC-MS/MS testing methods as a starting material in the preparation of calibrators, controls and linearity standards.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: A 20-oxo steroid that is pregn-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 20.
Related reactions
Linked notes
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