[(1R,2S,3S)-4-hydroxy-2,3,4-trimethyl-1-[(2'S,5S,8R,9S,10S,13S,14S,17S)-2',10,13-trimethyl-3-oxospiro[2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene-17,3'-oxirane]-2'-yl]pentyl] acetate

Details

• Internal ID: b3897de5-deb1-4b2a-9693-87b6c37233b0
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Ergostane steroids > Ergosterols and derivatives
• IUPAC Name: [(1R,2S,3S)-4-hydroxy-2,3,4-trimethyl-1-[(2'S,5S,8R,9S,10S,13S,14S,17S)-2',10,13-trimethyl-3-oxospiro[2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene-17,3'-oxirane]-2'-yl]pentyl] acetate
• SMILES (Canonical): CC(C(C)C(C)(C)O)C(C1(C2(O1)CCC3C2(CCC4C3CCC5C4(CCC(=O)C5)C)C)C)OC(=O)C
• SMILES (Isomeric): C[C@@H]([C@H](C)C(C)(C)O)[C@H]([C@]1([C@]2(O1)CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC[C@@H]5[C@@]4(CCC(=O)C5)C)C)C)OC(=O)C
• InChI: InChI=1S/C31H50O5/c1-18(19(2)27(4,5)34)26(35-20(3)32)30(8)31(36-30)16-13-25-23-10-9-21-17-22(33)11-14-28(21,6)24(23)12-15-29(25,31)7/h18-19,21,23-26,34H,9-17H2,1-8H3/t18-,19-,21-,23+,24-,25-,26+,28-,29-,30-,31-/m0/s1
• InChI Key: DLOIQQCWWNAIQK-YAOUQSKRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₅₀O₅
• Molecular Weight: 502.70 g/mol
• Exact Mass: 502.36582469 g/mol
• Topological Polar Surface Area (TPSA): 76.10 Ų
• XlogP: 5.60
• Atomic LogP (AlogP): 6.10
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9729	97.29%
Caco-2	-	0.6912	69.12%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6820	68.20%
OATP2B1 inhibitior	-	0.5713	57.13%
OATP1B1 inhibitior	+	0.8418	84.18%
OATP1B3 inhibitior	+	0.9496	94.96%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8257	82.57%
P-glycoprotein inhibitior	+	0.6733	67.33%
P-glycoprotein substrate	-	0.5449	54.49%
CYP3A4 substrate	+	0.7212	72.12%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8521	85.21%
CYP3A4 inhibition	-	0.8469	84.69%
CYP2C9 inhibition	-	0.7201	72.01%
CYP2C19 inhibition	-	0.7831	78.31%
CYP2D6 inhibition	-	0.9607	96.07%
CYP1A2 inhibition	-	0.7728	77.28%
CYP2C8 inhibition	+	0.5714	57.14%
CYP inhibitory promiscuity	-	0.9820	98.20%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6665	66.65%
Eye corrosion	-	0.9819	98.19%
Eye irritation	-	0.9248	92.48%
Skin irritation	-	0.6150	61.50%
Skin corrosion	-	0.9024	90.24%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4538	45.38%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.7975	79.75%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.7742	77.42%
Acute Oral Toxicity (c)	III	0.5505	55.05%
Estrogen receptor binding	+	0.7680	76.80%
Androgen receptor binding	+	0.7823	78.23%
Thyroid receptor binding	-	0.4878	48.78%
Glucocorticoid receptor binding	+	0.7434	74.34%
Aromatase binding	+	0.7477	74.77%
PPAR gamma	+	0.7115	71.15%
Honey bee toxicity	-	0.7664	76.64%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9650	96.50%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.40%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.56%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.03%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.47%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.65%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.61%	94.45%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	89.52%	89.05%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	89.51%	96.38%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.05%	100.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	88.35%	95.71%
CHEMBL204	P00734	Thrombin	86.36%	96.01%
CHEMBL1871	P10275	Androgen Receptor	85.65%	96.43%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.24%	93.04%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.23%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.47%	97.14%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.37%	91.07%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.26%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.95%	95.89%
CHEMBL3524	P56524	Histone deacetylase 4	83.90%	92.97%
CHEMBL5028	O14672	ADAM10	83.78%	97.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.21%	99.23%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.80%	95.89%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.90%	82.69%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.81%	93.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.56%	96.77%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.27%	92.62%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.12%	92.88%
CHEMBL2996	Q05655	Protein kinase C delta	80.95%	97.79%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.76%	89.50%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.50%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.33%	89.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.29%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.08%	86.33%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 21674161
• LOTUS: LTS0167164
• wikiData: Q104984546