2'-O-Acetylactein

Details

• Internal ID: c172a302-4144-4dbf-a649-29ffa43f202c
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Cycloartanols and derivatives
• IUPAC Name: [(1S,1'R,2S,3'R,4R,4'R,5R,5'R,6'R,10'S,12'S,13'S,16'R,18'S,21'R)-18'-[(2S,3R,4S,5R)-3-acetyloxy-4,5-dihydroxyoxan-2-yl]oxy-2-hydroxy-1,4',6',12',17',17'-hexamethylspiro[3,6-dioxabicyclo[3.1.0]hexane-4,8'-9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docosane]-3'-yl] acetate
• SMILES (Canonical): CC1CC2(C3C(O3)(C(O2)O)C)OC4C1C5(C(CC67CC68CCC(C(C8CCC7C5(C4)C)(C)C)OC9C(C(C(CO9)O)O)OC(=O)C)OC(=O)C)C
• SMILES (Isomeric): C[C@@H]1C[C@@]2([C@H]3[C@](O3)([C@H](O2)O)C)O[C@@H]4[C@H]1[C@]5([C@@H](C[C@@]67C[C@@]68CC[C@@H](C([C@@H]8CC[C@H]7[C@@]5(C4)C)(C)C)O[C@H]9[C@@H]([C@H]([C@@H](CO9)O)O)OC(=O)C)OC(=O)C)C
• InChI: InChI=1S/C39H58O12/c1-18-13-39(31-36(8,50-31)32(44)51-39)49-22-14-34(6)24-10-9-23-33(4,5)25(48-30-29(47-20(3)41)28(43)21(42)16-45-30)11-12-37(23)17-38(24,37)15-26(46-19(2)40)35(34,7)27(18)22/h18,21-32,42-44H,9-17H2,1-8H3/t18-,21-,22+,23+,24+,25+,26-,27+,28+,29-,30+,31-,32+,34+,35-,36+,37-,38+,39-/m1/s1
• InChI Key: KWPBPWVYOWXHER-KBHPJZKOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₅₈O₁₂
• Molecular Weight: 718.90 g/mol
• Exact Mass: 718.39282728 g/mol
• Topological Polar Surface Area (TPSA): 163.00 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 3.60
• H-Bond Acceptor: 12
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• 2'-Acetylactein
• 2'-O-Acetylactein, (-)-
• UNII-020NX485OR
• 020NX485OR
• 345968-83-4
• beta-D-Xylopyranoside, (3beta,12beta,16beta,23R,24R,25S,26S)-12-(acetyloxy)-16,23:23,26:24,25-triepoxy-26-hydroxy-9,19-cyclolanostan-3-yl, 2-acetate
• [(1S,1'R,2S,3'R,4R,4'R,5R,5'R,6'R,10'S,12'S,13'S,16'R,18'S,21'R)-18'-[(2S,3R,4S,5R)-3-acetyloxy-4,5-dihydroxyoxan-2-yl]oxy-2-hydroxy-1,4',6',12',17',17'-hexamethylspiro[3,6-dioxabicyclo[3.1.0]hexane-4,8'-9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docosane]-3'-yl] acetate
• 2'-O-acetyl-actein
• Q27231473
• .BETA.-D-XYLOPYRANOSIDE, (3.BETA.,12.BETA.,16.BETA.,23R,24R,25S,26S)-12-(ACETYLOXY)-16,23:23,26:24,25-TRIEPOXY-26-HYDROXY-9,19-CYCLOLANOSTAN-3-YL, 2-ACETATE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8755	87.55%
Caco-2	-	0.8636	86.36%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8053	80.53%
OATP2B1 inhibitior	-	0.8701	87.01%
OATP1B1 inhibitior	+	0.8332	83.32%
OATP1B3 inhibitior	+	0.8934	89.34%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	+	0.7803	78.03%
P-glycoprotein substrate	+	0.5747	57.47%
CYP3A4 substrate	+	0.7352	73.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8726	87.26%
CYP3A4 inhibition	-	0.7259	72.59%
CYP2C9 inhibition	-	0.7687	76.87%
CYP2C19 inhibition	-	0.8418	84.18%
CYP2D6 inhibition	-	0.9489	94.89%
CYP1A2 inhibition	-	0.8349	83.49%
CYP2C8 inhibition	+	0.7262	72.62%
CYP inhibitory promiscuity	-	0.9824	98.24%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6092	60.92%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9120	91.20%
Skin irritation	-	0.6521	65.21%
Skin corrosion	-	0.9209	92.09%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6555	65.55%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.7146	71.46%
skin sensitisation	-	0.8889	88.89%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.7323	73.23%
Acute Oral Toxicity (c)	I	0.4364	43.64%
Estrogen receptor binding	+	0.5873	58.73%
Androgen receptor binding	+	0.7504	75.04%
Thyroid receptor binding	-	0.5733	57.33%
Glucocorticoid receptor binding	+	0.7199	71.99%
Aromatase binding	+	0.7089	70.89%
PPAR gamma	+	0.7271	72.71%
Honey bee toxicity	-	0.6386	63.86%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5055	50.55%
Fish aquatic toxicity	+	0.9637	96.37%

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	97.79%	96.09%
CHEMBL204	P00734	Thrombin	94.30%	96.01%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.81%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.69%	96.77%
CHEMBL340	P08684	Cytochrome P450 3A4	90.32%	91.19%
CHEMBL3788	O00444	Serine/threonine-protein kinase PLK4	89.37%	83.65%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.23%	82.69%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	88.30%	92.88%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.03%	85.14%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	86.74%	98.99%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.25%	91.07%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.89%	89.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.92%	96.21%
CHEMBL2581	P07339	Cathepsin D	83.68%	98.95%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.65%	91.24%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	83.47%	94.78%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.86%	100.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.80%	95.71%
CHEMBL5028	O14672	ADAM10	82.52%	97.50%
CHEMBL5255	O00206	Toll-like receptor 4	82.22%	92.50%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	81.61%	98.75%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.44%	97.14%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.21%	100.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.95%	97.28%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.93%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.91%	96.61%

Plants that contains it

• Actaea cimicifuga
• Actaea dahurica
• Actaea racemosa
• Actaea simplex

Cross-Links

• PubChem: 21592425
• NPASS: NPC165163
• LOTUS: LTS0127200
• wikiData: Q27231473