Allopregnanolone

Details

• Internal ID: 040409bf-2d74-470a-8c4f-5ab65d3ead71
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Pregnane steroids > Gluco/mineralocorticoids, progestogins and derivatives
• IUPAC Name: 1-[(3R,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
• SMILES (Canonical): CC(=O)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)O)C)C
• SMILES (Isomeric): CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CC[C@H](C4)O)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
• InChI Key: AURFZBICLPNKBZ-SYBPFIFISA-N
• Popularity: 475 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₄O₂
• Molecular Weight: 318.50 g/mol
• Exact Mass: 318.255880323 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 4.90

Synonyms

• 516-54-1
• Brexanolone
• Allotetrahydroprogesterone
• 3alpha-hydroxy-5alpha-pregnan-20-one
• 3alpha,5alpha-THP
• brexanolona
• 3alpha-OH DHP
• brexanolonum
• 3alpha-Hydroxy-5alpha-dihydroprogesterone
• (3alpha,5alpha)-3-hydroxypregnan-20-one
• S39XZ5QV8Y
• 1-[(3R,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
• CHEBI:50169
• Pregnan-20-one, 3-hydroxy-, (3-alpha,5-alpha)-
• 1-((3R,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta(a)phenanthren-17-yl)ethanone
• 3 alpha Hydroxy 5 alpha pregnan 20 one
• 3 alpha-Hydroxy-5 alpha-pregnan-20-one
• 3beta-Hydroxy-5alpha-tetrahydroprogesterone
• alpha-Hydroxy-5 alpha-pregnan-20-one, 3
• alpha-pregnan-20-one, 3 alpha-Hydroxy-5
• Pregnan-20-one, 3-hydroxy-, (3beta,5alpha)-
• RefChem:56411
• Pregnanolone, (3alpha,5alpha)-
• 208-224-2
• 869-372-7
• Allopregnan-3alpha-ol-20-one
• SAGE-547
• Zulresso
• SGE-102
• (3alpha)-Allopregnanolone
• Brexanolone [USAN]
• 3a-Hydroxy-5a-pregnan-20-one
• (3a)-Allopregnanolone
• 3alpha,5alpha-tetrahydroprogesterone
• 3a,5a-THP
• CHEMBL207538
• 1-((3R,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethan-1-one
• 1-[(1S,3aS,3bR,5aS,7R,9aS,9bS,11aS)-7-hydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]ethan-1-one
• 3?-hydroxy-5?-pregnan-20-one
• Allopregnan-3.alpha.-ol-20-one
• tetrahydroprogesterone
• 3-alpha,5-alpha-Pregnanolone
• 3-alpha,5-alpha-Tetrahydroprogesterone
• Allopregnan-3?-ol-20-one
• Allopregnanolone(Brexanolone)
• 3a,5a-THPROG
• UNII-S39XZ5QV8Y
• Allopregnan-3a-ol-20-one
• BRN 3211363
• 5|A-Pregnan-3|A-Ol-20-One
• Allopregnalone
• 3-alpha-Hydroxy-5-alpha-pregnan-20-one
• Pregnan-20-one, 3-hydroxy-, (3a,5a)-
• Allopregnanolone?
• 3alpha-hydroxy-5alpha-pregnane-20-one
• 5alpha-pregnane-3alpha-ol-20-one
• Zulresso (TN)
• ALLO; Brexanolone; 3a,5a-tetrahydro Progesterone; 3a,5a-THP; (3a,5a)-3-hydroxy-pregnan-20-one
• Y4B
• 3a,5a-Pregnanolone
• 5-alpha-Pregnan-20-one, 3-alpha-hydroxy-
• BREXANOLONE [INN]
• 3-a-tetrahydroprogesterone
• Brexanolone (USAN/INN)
• Pregnan-20-one, 3-hydroxy-, (3.alpha.,5.alpha.)-
• Biomol-NT_000266
• 3a,5a-Tetrahydroprogesterone
• BIDD:PXR0069
• 5a-Pregnan-3a-ol-20-one
• BREXANOLONE [WHO-DD]
• SAGE547
• 3-alpha-tetrahydroprogesterone
• 3?-OH-DHP
• 4-08-00-00664 (Beilstein Handbook Reference)
• 5a-Pregnane-3a-ol-20-one
• orb422311
• SCHEMBL588060
• 5alpha-Pregnan-3a-ol-20-one
• BPBio1_000728
• GTPL4108
• 3a-Hydroxy-5a-pregnane-20-one
• Allopregnan-3I+/--ol-20-one
• BREXANOLONE [ORANGE BOOK]
• 3a-Hydroxy-5a-dihydroprogesterone
• AURFZBICLPNKBZ-SYBPFIFISA-N
• DEA NO. 2400
• 5alpha pregnan 3alpha ol 20 one
• DTXSID901016239
• GLXC-07897
• HMS3886D05
• 1-((3R,5S,8R,9S,10S,13S,14S,17S)-3-Hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone
• EX-A1195
• (3a,5a)-3-Hydroxypregnan-20-one
• BDBM50191342
• HB0932
• LMST02030156
• MFCD00003677
• MSK8589-100A
• s5805
• (+)-3a-Hydroxy-5a-pregnan-20-one
• AKOS024285177
• Pregnane-3alpha-ol-20-one, 5alpha-
• CS-6401
• DB11859
• 3|A,5|A-THP;SAGE-547;Brexanolone
• NCGC00163287-02
• 5alpha-Pregnan-3alpha-ol-20-one, solid
• AC-30353
• AS-76408
• DA-60419
• FA158661
• ST082264
• HY-101107
• NS00069758
• Allopregnanolone; Allopregnan-3|A-Ol-20-One
• ALLOPREGNAN-3.ALPHA.-OL-20-ONE [MI]
• D11149
• EN300-19731899
• BRD-K18172896-001-01-7
• BRD-K18172896-001-02-5
• Q28487680
• (+)-3.ALPHA.-HYDROXY-5.ALPHA.-PREGNAN-20-ONE
• 8E5D696A-EEBC-495D-A8C9-98FC9A593150
• (3alpha)-Allopregnanolone Solution in Acetonitrile, 100ug/mL
• 3beta-hydroxy-5beta,10alpha,14beta,17alpha-pregnan-20-one
• 3beta-hydroxy-5beta,10alpha,14beta,17alpha-pregnan-20-one; Brexanolone
• (1S,2S,7S,11S,14S,15S,5R,10R)-14-acetyl-5-hydroxy-2,15-dimethyltetracyclo[8.7. 0.0<2,7>.0<11,15>]heptadecane

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	160 nM	EC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.61%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.57%	100.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	89.08%	96.38%
CHEMBL221	P23219	Cyclooxygenase-1	87.01%	90.17%
CHEMBL204	P00734	Thrombin	86.71%	96.01%
CHEMBL340	P08684	Cytochrome P450 3A4	86.23%	91.19%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.68%	96.95%
CHEMBL237	P41145	Kappa opioid receptor	85.61%	98.10%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.29%	91.11%
CHEMBL1871	P10275	Androgen Receptor	84.19%	96.43%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.74%	93.04%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.42%	97.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.76%	82.69%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.42%	93.03%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 92786
• LOTUS: LTS0094148
• wikiData: Q2482223