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[(1S,2R,3R,5S,7S,9S,10R,11R,12S,14S,15R,16S,17S,22S,23S,24S,25R)-10,25-diacetyloxy-3,22-dihydroxy-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

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID 006a993e-82a3-4de8-971e-425dec4ac828
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name [(1S,2R,3R,5S,7S,9S,10R,11R,12S,14S,15R,16S,17S,22S,23S,24S,25R)-10,25-diacetyloxy-3,22-dihydroxy-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(C4C3OC(=O)C)C(C(=O)C6C5(C(C7C(C6)O7)OC(=O)C)C)O)OC(=O)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[C@H]5[C@H]([C@@H]4[C@H]3OC(=O)C)[C@H](C(=O)[C@@H]6[C@@]5([C@H]([C@@H]7[C@H](C6)O7)OC(=O)C)C)O)OC(=O)C)C)([C@](C(=O)O2)(C)O)C
InChI InChI=1S/C34H44O12/c1-12-9-20-33(7,34(8,41)30(40)46-20)24-22(12)32(6)19(42-13(2)35)11-16-21(23(32)28(24)43-14(3)36)26(39)25(38)17-10-18-27(45-18)29(31(16,17)5)44-15(4)37/h9,12,16-19,21-24,26-29,39,41H,10-11H2,1-8H3/t12-,16+,17-,18+,19+,21-,22+,23-,24-,26-,27+,28-,29+,31-,32-,33+,34-/m1/s1
InChI Key QPGVBFHVYONDKH-ZVVMTAGSSA-N
Popularity 5 references in papers

Physical and Chemical Properties

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Molecular Formula C34H44O12
Molecular Weight 644.70 g/mol
Exact Mass 644.28327683 g/mol
Topological Polar Surface Area (TPSA) 175.00 Ų
XlogP 2.10
Atomic LogP (AlogP) 1.87
H-Bond Acceptor 12
H-Bond Donor 2
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1S,2R,3R,5S,7S,9S,10R,11R,12S,14S,15R,16S,17S,22S,23S,24S,25R)-10,25-diacetyloxy-3,22-dihydroxy-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

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9746 97.46%
Caco-2 - 0.8129 81.29%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability - 0.6286 62.86%
Subcellular localzation Mitochondria 0.7222 72.22%
OATP2B1 inhibitior - 0.8624 86.24%
OATP1B1 inhibitior + 0.8120 81.20%
OATP1B3 inhibitior + 0.8715 87.15%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.9734 97.34%
P-glycoprotein inhibitior + 0.8122 81.22%
P-glycoprotein substrate - 0.9362 93.62%
CYP3A4 substrate + 0.7045 70.45%
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 + 0.5271 52.71%
CYP inhibitory promiscuity - 0.8438 84.38%
UGT catelyzed - 0.7000 70.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Danger 0.4574 45.74%
Eye corrosion - 0.9867 98.67%
Eye irritation - 0.8971 89.71%
Skin irritation - 0.5874 58.74%
Skin corrosion - 0.8991 89.91%
Ames mutagenesis - 0.6278 62.78%
Human Ether-a-go-go-Related Gene inhibition - 0.6191 61.91%
Micronuclear - 0.5000 50.00%
Hepatotoxicity + 0.5692 56.92%
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 + 0.7359 73.59%
Acute Oral Toxicity (c) I 0.3934 39.34%
Estrogen receptor binding + 0.7925 79.25%
Androgen receptor binding + 0.7361 73.61%
Thyroid receptor binding + 0.5491 54.91%
Glucocorticoid receptor binding + 0.7509 75.09%
Aromatase binding + 0.7066 70.66%
PPAR gamma + 0.7346 73.46%
Honey bee toxicity - 0.6815 68.15%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity - 0.5602 56.02%
Fish aquatic toxicity + 0.9791 97.91%

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 99.77% 83.82%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 97.48% 94.45%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 97.07% 85.14%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.89% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 95.53% 86.33%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.54% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 92.76% 97.25%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.47% 95.56%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 91.26% 96.77%
CHEMBL340 P08684 Cytochrome P450 3A4 90.19% 91.19%
CHEMBL1994 P08235 Mineralocorticoid receptor 88.08% 100.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.06% 89.00%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 86.53% 93.00%
CHEMBL2581 P07339 Cathepsin D 86.40% 98.95%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 86.32% 94.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 83.40% 99.23%
CHEMBL3137262 O60341 LSD1/CoREST complex 82.60% 97.09%
CHEMBL2413 P32246 C-C chemokine receptor type 1 82.13% 89.50%
CHEMBL5852 Q96P65 Pyroglutamylated RFamide peptide receptor 80.74% 85.00%
CHEMBL4208 P20618 Proteasome component C5 80.61% 90.00%
CHEMBL3401 O75469 Pregnane X receptor 80.59% 94.73%

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
Tacca plantaginea

Cross-Links

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PubChem 101259325
LOTUS LTS0016070
wikiData Q105225379