17-(5-ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

Details

• Internal ID: 74b42fbb-f871-455f-a898-55b1ba3c35fb
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Stigmastanes and derivatives
• IUPAC Name: 17-(5-ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
• SMILES (Canonical): CCC(CCC(C)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)O)C)C)C(C)C
• SMILES (Isomeric): CCC(CCC(C)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)O)C)C)C(C)C
• InChI: InChI=1S/C29H52O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h19-27,30H,7-18H2,1-6H3
• InChI Key: LGJMUZUPVCAVPU-UHFFFAOYSA-N
• Popularity: 139 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₅₂O
• Molecular Weight: 416.70 g/mol
• Exact Mass: 416.401816278 g/mol
• Topological Polar Surface Area (TPSA): 20.20 Ų
• XlogP: 10.20
• Atomic LogP (AlogP): 8.10
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• Fucostanol
• beta-Sitostanol
• C29H52O
• Dihydrositosterol
• 19466-47-8
• Stigmastane-3-beta-ol
• C29-H52-O
• SCHEMBL12820619
• LGJMUZUPVCAVPU-UHFFFAOYSA-N
• (3 beta,5 alpha)-stigmastan- 3-ol
• 17-(5-ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
• LS-177724
• 24 alpha-ethyl-5 alpha-cholestan-3 beta-ol
• 24 alpha-ethyl-5 beta-cholestan-3 alpha-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.5068	50.68%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Lysosomes	0.5430	54.30%
OATP2B1 inhibitior	+	0.5501	55.01%
OATP1B1 inhibitior	-	0.3305	33.05%
OATP1B3 inhibitior	+	0.9656	96.56%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.5617	56.17%
P-glycoprotein substrate	+	0.6025	60.25%
CYP3A4 substrate	+	0.7149	71.49%
CYP2C9 substrate	-	0.6165	61.65%
CYP2D6 substrate	+	0.3527	35.27%
CYP3A4 inhibition	-	0.8684	86.84%
CYP2C9 inhibition	-	0.7611	76.11%
CYP2C19 inhibition	-	0.8361	83.61%
CYP2D6 inhibition	-	0.9574	95.74%
CYP1A2 inhibition	-	0.7423	74.23%
CYP2C8 inhibition	-	0.7888	78.88%
CYP inhibitory promiscuity	-	0.7255	72.55%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6901	69.01%
Eye corrosion	-	0.9741	97.41%
Eye irritation	-	0.8373	83.73%
Skin irritation	+	0.5355	53.55%
Skin corrosion	-	0.9031	90.31%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6180	61.80%
Micronuclear	-	1.0000	100.00%
Hepatotoxicity	-	0.5619	56.19%
skin sensitisation	+	0.6370	63.70%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.8891	88.91%
Acute Oral Toxicity (c)	III	0.7528	75.28%
Estrogen receptor binding	+	0.7810	78.10%
Androgen receptor binding	+	0.8196	81.96%
Thyroid receptor binding	+	0.6292	62.92%
Glucocorticoid receptor binding	+	0.7795	77.95%
Aromatase binding	+	0.5425	54.25%
PPAR gamma	-	0.5133	51.33%
Honey bee toxicity	-	0.7359	73.59%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9749	97.49%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL240	Q12809	HERG	97.11%	89.76%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.67%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.47%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	93.09%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.71%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.40%	97.09%
CHEMBL238	Q01959	Dopamine transporter	89.12%	95.88%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.21%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.73%	100.00%
CHEMBL1871	P10275	Androgen Receptor	87.05%	96.43%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.01%	82.69%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.66%	90.71%
CHEMBL237	P41145	Kappa opioid receptor	86.06%	98.10%
CHEMBL2581	P07339	Cathepsin D	85.24%	98.95%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	84.86%	89.05%
CHEMBL220	P22303	Acetylcholinesterase	84.76%	94.45%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.05%	89.62%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	84.04%	96.38%
CHEMBL268	P43235	Cathepsin K	83.48%	96.85%
CHEMBL226	P30542	Adenosine A1 receptor	83.13%	95.93%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.04%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.95%	91.11%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	81.73%	97.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.52%	93.56%
CHEMBL2094135	Q96BI3	Gamma-secretase	80.55%	98.05%
CHEMBL4581	P52732	Kinesin-like protein 1	80.50%	93.18%
CHEMBL242	Q92731	Estrogen receptor beta	80.47%	98.35%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	80.45%	92.88%
CHEMBL202	P00374	Dihydrofolate reductase	80.06%	89.92%

Plants that contains it

• Abies sachalinensis
• Alnus japonica
• Aloe rubroviolacea
• Alsophila podophylla
• Alsophila spinulosa
• Arabidopsis thaliana
• Calycanthus floridus
• Cannabis sativa
• Chelonanthus albus
• Clerodendrum chinense
• Conium maculatum
• Costus tonkinensis
• Cymodocea nodosa
• Diplopterygium glaucum
• Dracaena cinnabari
• Drimia sanguinea
• Hedysarum setigerum
• Heterotheca inuloides
• Hippophae rhamnoides
• Isodon japonicus
• Isodon lophanthoides
• Kalanchoe petitiana
• Lessingianthus mollissimus
• Panax quinquefolius
• Parodia scopa
• Pinus wallichiana
• Salsola collina
• Saussurea controversa
• Setaria italica
• Stephania sinica
• Syzygium siamense
• Virola venosa
• Zea mays

Cross-Links

• PubChem: 6743
• NPASS: NPC287433
• LOTUS: LTS0045337
• wikiData: Q69756918