taccalonolide AJ

Details

• Internal ID: ba06f31f-9c80-4245-b4e7-8670fed61926
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: [(1S,2S,3R,5S,7S,9S,10R,11R,12S,13S,14R,15R,16S,17S,18S,20S,23S,24S,25R,26R)-10,14-diacetyloxy-3,23,26-trihydroxy-11,15,17,23,24-pentamethyl-4,22-dioxo-8,19,21-trioxaoctacyclo[13.11.0.02,12.05,11.07,9.016,25.018,20.020,24]hexacosan-13-yl] acetate
• SMILES (Canonical): CC1C2C(C(C3C2(C(C(C4C3C(C(=O)C5C4(C(C6C(C5)O6)OC(=O)C)C)O)OC(=O)C)OC(=O)C)C)O)C7(C(C(=O)OC78C1O8)(C)O)C
• SMILES (Isomeric): C[C@H]1[C@H]2[C@@H]([C@@H]([C@@H]3[C@@]2([C@H]([C@H]([C@H]4[C@H]3[C@H](C(=O)[C@@H]5[C@@]4([C@H]([C@@H]6[C@H](C5)O6)OC(=O)C)C)O)OC(=O)C)OC(=O)C)C)O)[C@]7([C@](C(=O)O[C@]78[C@H]1O8)(C)O)C
• InChI: InChI=1S/C34H44O14/c1-10-17-20(32(7)33(8,42)29(41)48-34(32)26(10)47-34)23(40)18-16-19(25(43-11(2)35)28(31(17,18)6)45-13(4)37)30(5)14(21(38)22(16)39)9-15-24(46-15)27(30)44-12(3)36/h10,14-20,22-28,39-40,42H,9H2,1-8H3/t10-,14+,15-,16-,17-,18+,19+,20-,22+,23+,24-,25-,26-,27-,28-,30-,31+,32-,33+,34+/m0/s1
• InChI Key: BWKYBGRKQMTOQL-MPOFNYKTSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₄O₁₄
• Molecular Weight: 676.70 g/mol
• Exact Mass: 676.27310607 g/mol
• Topological Polar Surface Area (TPSA): 208.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.05
• H-Bond Acceptor: 14
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• 1349904-82-0
• [(1S,2S,3R,5S,7S,9S,10R,11R,12S,13S,14R,15R,16S,17S,18S,20S,23S,24S,25R,26R)-10,14-diacetyloxy-3,23,26-trihydroxy-11,15,17,23,24-pentamethyl-4,22-dioxo-8,19,21-trioxaoctacyclo[13.11.0.02,12.05,11.07,9.016,25.018,20.020,24]hexacosan-13-yl] acetate
• CHEMBL2408398
• HY-N4208
• AKOS040760730
• MS-31071
• PD125320
• CS-0032438

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9305	93.05%
Caco-2	-	0.8377	83.77%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6464	64.64%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8408	84.08%
OATP1B3 inhibitior	+	0.8909	89.09%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8537	85.37%
P-glycoprotein inhibitior	+	0.7468	74.68%
P-glycoprotein substrate	-	0.6205	62.05%
CYP3A4 substrate	+	0.6919	69.19%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8590	85.90%
CYP3A4 inhibition	-	0.8145	81.45%
CYP2C9 inhibition	-	0.9190	91.90%
CYP2C19 inhibition	-	0.8955	89.55%
CYP2D6 inhibition	-	0.9364	93.64%
CYP1A2 inhibition	-	0.9277	92.77%
CYP2C8 inhibition	+	0.4879	48.79%
CYP inhibitory promiscuity	-	0.9002	90.02%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4544	45.44%
Eye corrosion	-	0.9835	98.35%
Eye irritation	-	0.8950	89.50%
Skin irritation	-	0.6917	69.17%
Skin corrosion	-	0.8707	87.07%
Ames mutagenesis	-	0.6178	61.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.6199	61.99%
Micronuclear	-	0.5141	51.41%
Hepatotoxicity	+	0.6418	64.18%
skin sensitisation	-	0.8224	82.24%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.7609	76.09%
Acute Oral Toxicity (c)	III	0.3241	32.41%
Estrogen receptor binding	+	0.7146	71.46%
Androgen receptor binding	+	0.7400	74.00%
Thyroid receptor binding	-	0.4912	49.12%
Glucocorticoid receptor binding	+	0.6983	69.83%
Aromatase binding	+	0.6669	66.69%
PPAR gamma	+	0.7286	72.86%
Honey bee toxicity	-	0.6685	66.85%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5265	52.65%
Fish aquatic toxicity	+	0.8709	87.09%

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	97.68%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.96%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.48%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.90%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	92.73%	90.17%
CHEMBL2581	P07339	Cathepsin D	91.77%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	91.11%	91.19%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	90.05%	96.77%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.60%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.92%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.15%	97.25%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.99%	91.24%
CHEMBL5255	O00206	Toll-like receptor 4	86.31%	92.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.15%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.56%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.78%	92.94%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	82.05%	81.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.67%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.48%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.45%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.09%	95.89%

Plants that contains it

• Tacca chantrieri

Cross-Links

• PubChem: 56926890
• NPASS: NPC97002
• ChEMBL: CHEMBL2408398