Cholesteryl acetate

Details

• Internal ID: d9fa47a9-a2e6-4684-9930-a03383510d5d
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid esters > Cholesteryl esters
• IUPAC Name: [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• SMILES (Canonical): CC(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)OC(=O)C)C)C
• SMILES (Isomeric): C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)OC(=O)C)C)C
• InChI: InChI=1S/C29H48O2/c1-19(2)8-7-9-20(3)25-12-13-26-24-11-10-22-18-23(31-21(4)30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-20,23-27H,7-9,11-18H2,1-6H3/t20-,23+,24+,25-,26+,27+,28+,29-/m1/s1
• InChI Key: XUGISPSHIFXEHZ-VEVYEIKRSA-N
• Popularity: 587 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₈O₂
• Molecular Weight: 428.70 g/mol
• Exact Mass: 428.365430770 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 9.10
• Atomic LogP (AlogP): 7.96
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• 604-35-3
• Cholesterol acetate
• 3b-Acetoxycholest-5-ene
• 3beta-Acetoxycholest-5-ene
• Cholesterol 3-acetate
• Cholesterin acetate
• (-)-Cholesteryl acetate
• Cholest-5-en-3beta-ol acetate
• Cholest-5-en-3beta-yl acetate
• 3-Cholesteryl acetate
• Cholesterylacetate
• Cholesterol, acetate
• UNII-OTA9A3781T
• OTA9A3781T
• CHEBI:78242
• (3beta)-cholest-5-en-3-yl acetate
• CCRIS 5350
• Cholest-5-en-3-beta-yl acetate
• NSC 8799
• EINECS 210-066-4
• MFCD00003636
• AI3-24120
• Cholest-5-en-3-ol (3.beta.)-, acetate
• Acetic Acid Cholesterol Ester
• Cholest-5-en-3-yl acetate #
• C29H48O2
• NSC-8799
• Acetyl Cholesterol
• Cholest-5-en-3-ol (3beta)-, acetate
• Cholest-5-en-3-ol, acetate, (3.beta.)-
• 3a-Cholesterol acetate
• Cholesterol 3b-acetate
• cholesterol 3beta-acetate
• Cholesteryl acetate, 97%
• SCHEMBL25655
• Cholest-5-en-3b-ol acetate
• Cholest-5-en-3b-yl acetate
• CHEMBL3138728
• DTXSID60889358
• CHOLESTERYL ACETATE [INCI]
• (3b)-Cholest-5-en-3-ol acetate
• CHOLESTEROL 3.BETA.-ACETATE
• (3beta)-cholest-5-en-3-ol acetate
• LMST01010245
• s4968
• ACETIC ACID, CHOLESTEROL ESTER
• AKOS015955666
• s10712
• (3I(2))-cholest-5-en-3-yl ethanoate
• [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• AS-57181
• Cholest-5-en-3-ol (3beta)-, 3-acetate
• CS-0030699
• Cholest-5-en-3-ol (3.beta.)-, 3-acetate
• A868978
• CHOLEST-5-ENE-3-OL (3.BETA.)-, ACETATE
• W-105252
• Q27147700
• (3S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate
• [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]acetate
• cholest-5-en-3-yl acetate; Chloesteryl acetate; Acetic acid cholesteryl ester; Cholesterol Acetate
• Cholesterin acetate; Cholesterol 3-acetate; Cholesterol 3-acetate; Cholesteryl acetate; NSC 8799

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	-	0.5496	54.96%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6637	66.37%
OATP2B1 inhibitior	-	0.7128	71.28%
OATP1B1 inhibitior	+	0.9623	96.23%
OATP1B3 inhibitior	-	0.5698	56.98%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.9365	93.65%
P-glycoprotein inhibitior	+	0.6866	68.66%
P-glycoprotein substrate	+	0.6351	63.51%
CYP3A4 substrate	+	0.7542	75.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8603	86.03%
CYP3A4 inhibition	-	0.8659	86.59%
CYP2C9 inhibition	-	0.8900	89.00%
CYP2C19 inhibition	+	0.6666	66.66%
CYP2D6 inhibition	-	0.9467	94.67%
CYP1A2 inhibition	-	0.9277	92.77%
CYP2C8 inhibition	-	0.6011	60.11%
CYP inhibitory promiscuity	-	0.6517	65.17%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4964	49.64%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9226	92.26%
Skin irritation	+	0.5372	53.72%
Skin corrosion	-	0.9829	98.29%
Ames mutagenesis	-	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6429	64.29%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.5637	56.37%
skin sensitisation	+	0.6011	60.11%
Respiratory toxicity	+	0.9111	91.11%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.7687	76.87%
Acute Oral Toxicity (c)	III	0.8629	86.29%
Estrogen receptor binding	+	0.8522	85.22%
Androgen receptor binding	+	0.6387	63.87%
Thyroid receptor binding	-	0.5921	59.21%
Glucocorticoid receptor binding	+	0.7600	76.00%
Aromatase binding	+	0.5305	53.05%
PPAR gamma	+	0.6156	61.56%
Honey bee toxicity	-	0.8183	81.83%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5505	55.05%
Fish aquatic toxicity	+	0.9970	99.70%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.99%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.93%	94.45%
CHEMBL2581	P07339	Cathepsin D	96.64%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.06%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.45%	91.11%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	94.61%	95.89%
CHEMBL3359	P21462	Formyl peptide receptor 1	90.83%	93.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.72%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.41%	100.00%
CHEMBL2179	P04062	Beta-glucocerebrosidase	86.55%	85.31%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.49%	82.69%
CHEMBL226	P30542	Adenosine A1 receptor	85.89%	95.93%
CHEMBL237	P41145	Kappa opioid receptor	83.68%	98.10%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.58%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.93%	99.17%
CHEMBL5028	O14672	ADAM10	82.05%	97.50%
CHEMBL340	P08684	Cytochrome P450 3A4	81.19%	91.19%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	80.85%	94.08%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.61%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.07%	95.89%

Plants that contains it

• Achillea leptophylla
• Aegiphila obducta
• Aldama cordifolia
• Baccharoides anthelmintica
• Cajanus cajan
• Cordiera macrophylla
• Dioscorea futschauensis
• Dioscorea polystachya
• Dorstenia barnimiana
• Petrosedum forsterianum
• Rubia yunnanensis
• Uvaria mocoli
• Verbascum georgicum
• Wrightia tinctoria
• Zea mays
• Zieria chevalieri

Cross-Links

• PubChem: 2723897
• NPASS: NPC153987
• LOTUS: LTS0004289
• wikiData: Q27147700