[(1S,2R,3R,5S,7S,9R,10R,11R,12S,14S,15R,16S,17S,22R,23S,25R)-3,10,22,25-tetrahydroxy-11,15,17,22,23-pentamethyl-4,21-dioxo-8,20-dioxaheptacyclo[13.10.0.02,12.05,11.07,9.016,24.019,23]pentacos-18-en-14-yl] acetate

Details

• Internal ID: ba1fbe45-9af8-4d34-9e75-a48609cfe792
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: [(1S,2R,3R,5S,7S,9R,10R,11R,12S,14S,15R,16S,17S,22R,23S,25R)-3,10,22,25-tetrahydroxy-11,15,17,22,23-pentamethyl-4,21-dioxo-8,20-dioxaheptacyclo[13.10.0.02,12.05,11.07,9.016,24.019,23]pentacos-18-en-14-yl] acetate
• SMILES (Canonical): CC1C=C2C(C3C1C4(C(CC5C(C4C3O)C(C(=O)C6C5(C(C7C(C6)O7)O)C)O)OC(=O)C)C)(C(C(=O)O2)(C)O)C
• SMILES (Isomeric): C[C@@H]1C=C2[C@@](C3[C@H]1[C@]4([C@H](C[C@H]5[C@H]([C@@H]4[C@H]3O)[C@H](C(=O)[C@@H]6[C@@]5([C@H]([C@@H]7[C@H](C6)O7)O)C)O)OC(=O)C)C)([C@@](C(=O)O2)(C)O)C
• InChI: InChI=1S/C30H40O10/c1-10-7-16-29(5,30(6,37)26(36)40-16)20-18(10)28(4)15(38-11(2)31)9-12-17(19(28)23(20)34)22(33)21(32)13-8-14-24(39-14)25(35)27(12,13)3/h7,10,12-15,17-20,22-25,33-35,37H,8-9H2,1-6H3/t10-,12+,13-,14+,15+,17-,18+,19-,20?,22-,23-,24+,25+,27-,28-,29+,30+/m1/s1
• InChI Key: LOEZWMNSGZLOSK-DSASIYGNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₀O₁₀
• Molecular Weight: 560.60 g/mol
• Exact Mass: 560.26214747 g/mol
• Topological Polar Surface Area (TPSA): 163.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 0.73
• H-Bond Acceptor: 10
• H-Bond Donor: 4
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9746	97.46%
Caco-2	-	0.7984	79.84%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7222	72.22%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8333	83.33%
OATP1B3 inhibitior	+	0.8715	87.15%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7966	79.66%
P-glycoprotein inhibitior	+	0.6413	64.13%
P-glycoprotein substrate	-	0.8962	89.62%
CYP3A4 substrate	+	0.7142	71.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8653	86.53%
CYP3A4 inhibition	-	0.8064	80.64%
CYP2C9 inhibition	-	0.8787	87.87%
CYP2C19 inhibition	-	0.8800	88.00%
CYP2D6 inhibition	-	0.9444	94.44%
CYP1A2 inhibition	-	0.7861	78.61%
CYP2C8 inhibition	+	0.5243	52.43%
CYP inhibitory promiscuity	-	0.8438	84.38%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Danger	0.4574	45.74%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.9155	91.55%
Skin irritation	-	0.5874	58.74%
Skin corrosion	-	0.8991	89.91%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5215	52.15%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	+	0.6567	65.67%
skin sensitisation	-	0.7879	78.79%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.6829	68.29%
Acute Oral Toxicity (c)	I	0.3934	39.34%
Estrogen receptor binding	+	0.7628	76.28%
Androgen receptor binding	+	0.7346	73.46%
Thyroid receptor binding	+	0.5477	54.77%
Glucocorticoid receptor binding	+	0.6856	68.56%
Aromatase binding	+	0.7404	74.04%
PPAR gamma	+	0.6275	62.75%
Honey bee toxicity	-	0.7129	71.29%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9791	97.91%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.06%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.78%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.38%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.65%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.12%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.66%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.58%	96.77%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.50%	89.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.46%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.37%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.88%	94.00%
CHEMBL340	P08684	Cytochrome P450 3A4	86.72%	91.19%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	85.75%	97.21%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.59%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.64%	97.25%
CHEMBL5255	O00206	Toll-like receptor 4	82.48%	92.50%
CHEMBL4208	P20618	Proteasome component C5	82.12%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.72%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	81.01%	94.73%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.78%	93.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.44%	92.94%
CHEMBL2581	P07339	Cathepsin D	80.36%	98.95%

Plants that contains it

• Tacca chantrieri

Cross-Links

• PubChem: 102434357
• NPASS: NPC18220