[(1S,2S,3R,5S,7S,9S,10R,11S,12S,13S,14R,15R,16S,17S,22S,23S,24R,25R)-3,10,13-triacetyloxy-5,14,22-trihydroxy-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-25-yl] acetate

Details

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Internal ID b6babac9-489d-483f-894e-2015bb9e0881
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name [(1S,2S,3R,5S,7S,9S,10R,11S,12S,13S,14R,15R,16S,17S,22S,23S,24R,25R)-3,10,13-triacetyloxy-5,14,22-trihydroxy-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-25-yl] acetate
SMILES (Canonical) CC1C=C2C(C3C1C4(C(C3OC(=O)C)C5C(C(C4O)OC(=O)C)C6(C(C7C(O7)CC6(C(=O)C5OC(=O)C)O)OC(=O)C)C)C)(C(C(=O)O2)(C)O)C
SMILES (Isomeric) C[C@@H]1C=C2[C@@]([C@H]3[C@H]1[C@@]4([C@@H]([C@H]3OC(=O)C)[C@H]5[C@H]([C@@H]([C@@H]4O)OC(=O)C)[C@]6([C@H]([C@@H]7[C@@H](O7)C[C@]6(C(=O)[C@@H]5OC(=O)C)O)OC(=O)C)C)C)([C@](C(=O)O2)(C)O)C
InChI InChI=1S/C36H46O15/c1-12-10-18-33(7,35(9,44)31(43)51-18)23-20(12)32(6)21(26(23)47-14(3)38)19-22(27(28(32)41)48-15(4)39)34(8)30(49-16(5)40)24-17(50-24)11-36(34,45)29(42)25(19)46-13(2)37/h10,12,17,19-28,30,41,44-45H,11H2,1-9H3/t12-,17+,19+,20+,21-,22-,23+,24+,25-,26-,27+,28+,30+,32-,33+,34+,35-,36-/m1/s1
InChI Key GLBBNXPRMRGGIZ-PLTXRRTJSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C36H46O15
Molecular Weight 718.70 g/mol
Exact Mass 718.28367076 g/mol
Topological Polar Surface Area (TPSA) 222.00 Ų
XlogP 0.90
Atomic LogP (AlogP) 0.53
H-Bond Acceptor 15
H-Bond Donor 3
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1S,2S,3R,5S,7S,9S,10R,11S,12S,13S,14R,15R,16S,17S,22S,23S,24R,25R)-3,10,13-triacetyloxy-5,14,22-trihydroxy-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-25-yl] acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9882 98.82%
Caco-2 - 0.8292 82.92%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability - 0.7857 78.57%
Subcellular localzation Mitochondria 0.6566 65.66%
OATP2B1 inhibitior - 0.8582 85.82%
OATP1B1 inhibitior + 0.8436 84.36%
OATP1B3 inhibitior + 0.9064 90.64%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior + 0.9481 94.81%
P-glycoprotein inhibitior + 0.7998 79.98%
P-glycoprotein substrate - 0.6475 64.75%
CYP3A4 substrate + 0.7022 70.22%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8653 86.53%
CYP3A4 inhibition - 0.7804 78.04%
CYP2C9 inhibition - 0.9265 92.65%
CYP2C19 inhibition - 0.9221 92.21%
CYP2D6 inhibition - 0.9330 93.30%
CYP1A2 inhibition - 0.9021 90.21%
CYP2C8 inhibition + 0.5000 50.00%
CYP inhibitory promiscuity - 0.8912 89.12%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Danger 0.5147 51.47%
Eye corrosion - 0.9831 98.31%
Eye irritation - 0.8991 89.91%
Skin irritation - 0.6045 60.45%
Skin corrosion - 0.8921 89.21%
Ames mutagenesis + 0.5600 56.00%
Human Ether-a-go-go-Related Gene inhibition - 0.6569 65.69%
Micronuclear + 0.5259 52.59%
Hepatotoxicity + 0.6283 62.83%
skin sensitisation - 0.7613 76.13%
Respiratory toxicity + 0.7778 77.78%
Reproductive toxicity + 0.8444 84.44%
Mitochondrial toxicity + 0.8250 82.50%
Nephrotoxicity + 0.8227 82.27%
Acute Oral Toxicity (c) III 0.3642 36.42%
Estrogen receptor binding + 0.7585 75.85%
Androgen receptor binding + 0.7343 73.43%
Thyroid receptor binding + 0.5545 55.45%
Glucocorticoid receptor binding + 0.7022 70.22%
Aromatase binding + 0.6789 67.89%
PPAR gamma + 0.7134 71.34%
Honey bee toxicity - 0.7112 71.12%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5700 57.00%
Fish aquatic toxicity + 0.9409 94.09%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL4040 P28482 MAP kinase ERK2 99.15% 83.82%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 98.95% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.88% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.23% 96.09%
CHEMBL2581 P07339 Cathepsin D 94.59% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.27% 86.33%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 91.54% 96.77%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.50% 95.56%
CHEMBL340 P08684 Cytochrome P450 3A4 90.53% 91.19%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 89.81% 85.14%
CHEMBL1994 P08235 Mineralocorticoid receptor 88.20% 100.00%
CHEMBL253 P34972 Cannabinoid CB2 receptor 86.07% 97.25%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 85.68% 94.00%
CHEMBL241 Q14432 Phosphodiesterase 3A 85.53% 92.94%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.55% 89.00%
CHEMBL4208 P20618 Proteasome component C5 83.28% 90.00%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 83.12% 93.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 83.09% 99.23%
CHEMBL4803 P29474 Nitric-oxide synthase, endothelial 81.88% 86.00%
CHEMBL2413 P32246 C-C chemokine receptor type 1 81.78% 89.50%
CHEMBL3401 O75469 Pregnane X receptor 81.53% 94.73%
CHEMBL5852 Q96P65 Pyroglutamylated RFamide peptide receptor 81.49% 85.00%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 80.00% 95.50%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Tacca chantrieri

Cross-Links

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PubChem 163027236
LOTUS LTS0037509
wikiData Q105010744