Pregnenolone

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	4eb4ab50-e6c2-4a50-b305-914c6961104e
Taxonomy	Lipids and lipid-like molecules > Steroids and steroid derivatives > Pregnane steroids > Gluco/mineralocorticoids, progestogins and derivatives
IUPAC Name	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
SMILES (Canonical)	CC(=O)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
SMILES (Isomeric)	CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)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
InChI Key	ORNBQBCIOKFOEO-QGVNFLHTSA-N
Popularity	9,277 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₁H₃₂O₂
Molecular Weight	316.50 g/mol
Exact Mass	316.240230259 g/mol
Topological Polar Surface Area (TPSA)	37.30 Å²
XlogP	4.20
Atomic LogP (AlogP)	4.52
H-Bond Acceptor	2
H-Bond Donor	1
Rotatable Bonds	1

Synonyms

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145-13-1

Arthenolone

Regnosone

Skinostelon

Enelone

3beta-Hydroxypregn-5-en-20-one

Natolone

5-Pregnen-3beta-ol-20-one

Bina-Skin

delta5-Pregnenolone

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.7590	75.90%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6747	67.47%
OATP2B1 inhibitior	-	0.8752	87.52%
OATP1B1 inhibitior	+	0.9235	92.35%
OATP1B3 inhibitior	+	0.9811	98.11%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.7250	72.50%
BSEP inhibitior	+	0.8250	82.50%
P-glycoprotein inhibitior	-	0.6963	69.63%
P-glycoprotein substrate	+	0.6312	63.12%
CYP3A4 substrate	+	0.7980	79.80%
CYP2C9 substrate	-	0.8495	84.95%
CYP2D6 substrate	-	0.7671	76.71%
CYP3A4 inhibition	-	0.8332	83.32%
CYP2C9 inhibition	-	0.9333	93.33%
CYP2C19 inhibition	-	0.9023	90.23%
CYP2D6 inhibition	-	0.9558	95.58%
CYP1A2 inhibition	-	0.9179	91.79%
CYP2C8 inhibition	-	0.6282	62.82%
CYP inhibitory promiscuity	-	0.9076	90.76%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Warning	0.5003	50.03%
Eye corrosion	-	0.9940	99.40%
Eye irritation	-	0.9727	97.27%
Skin irritation	+	0.6734	67.34%
Skin corrosion	-	0.9696	96.96%
Ames mutagenesis	-	0.8774	87.74%
Human Ether-a-go-go-Related Gene inhibition	-	0.5172	51.72%
Micronuclear	-	0.9500	95.00%
Hepatotoxicity	+	0.6986	69.86%
skin sensitisation	+	0.5197	51.97%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.6665	66.65%
Acute Oral Toxicity (c)	III	0.6090	60.90%
Estrogen receptor binding	+	0.8667	86.67%
Androgen receptor binding	+	0.6849	68.49%
Thyroid receptor binding	+	0.8462	84.62%
Glucocorticoid receptor binding	+	0.9213	92.13%
Aromatase binding	-	0.6391	63.91%
PPAR gamma	-	0.7803	78.03%
Honey bee toxicity	-	0.8278	82.78%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9825	98.25%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2421	P08185	Corticosteroid binding globulin	5888.44 nM	Ki	PMID: 15139751
CHEMBL1293235	P02545	Prelamin-A/C	35481.3 nM	Potency	via CMAUP
CHEMBL3305	P04278	Testis-specific androgen-binding protein	70.79 nM	Kd	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	97.32%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	93.65%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.41%	91.11%
CHEMBL2581	P07339	Cathepsin D	88.27%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	84.58%	95.93%
CHEMBL221	P23219	Cyclooxygenase-1	84.41%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.30%	95.56%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.21%	93.04%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.87%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.70%	89.00%
CHEMBL5028	O14672	ADAM10	81.07%	97.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.67%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.26%	90.71%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Acanthosyris spinescens

Ageratina saltillensis

Aglaia elaeagnoidea

Agrimonia eupatoria

Alluaudia humbertii

Alstonia lanceolifera

Angelica archangelica

Angelica keiskei

Aristolochia littoralis

Astragalus gummifer

Campanula medium

Cardiospermum halicacabum