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[(1S,2R,6S,7R,9R,11S,12S,14R,15R,16S,17R)-17-acetyloxy-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-6-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-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 e6997684-7faa-437b-9618-9f7304088ce0
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name [(1S,2R,6S,7R,9R,11S,12S,14R,15R,16S,17R)-17-acetyloxy-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-6-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-14-yl] acetate
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(C)C2C(CC3C2(C(CC4C3CC5C6(C4(C(=O)C=CC6O)C)O5)OC(=O)C)C)OC(=O)C)C
SMILES (Isomeric) CC1=C(C(=O)O[C@H](C1)[C@@H](C)[C@H]2[C@@H](C[C@@H]3[C@@]2([C@@H](C[C@H]4[C@H]3C[C@@H]5[C@]6([C@@]4(C(=O)C=C[C@@H]6O)C)O5)OC(=O)C)C)OC(=O)C)C
InChI InChI=1S/C32H42O9/c1-14-10-22(40-29(37)15(14)2)16(3)28-23(38-17(4)33)12-20-19-11-27-32(41-27)25(36)9-8-24(35)31(32,7)21(19)13-26(30(20,28)6)39-18(5)34/h8-9,16,19-23,25-28,36H,10-13H2,1-7H3/t16-,19+,20+,21+,22-,23-,25+,26-,27-,28+,30-,31+,32-/m1/s1
InChI Key RACMXXSRKKLJFQ-XIJHRULCSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C32H42O9
Molecular Weight 570.70 g/mol
Exact Mass 570.28288291 g/mol
Topological Polar Surface Area (TPSA) 129.00 Ų
XlogP 3.00
Atomic LogP (AlogP) 3.46
H-Bond Acceptor 9
H-Bond Donor 1
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1S,2R,6S,7R,9R,11S,12S,14R,15R,16S,17R)-17-acetyloxy-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-6-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-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 + 0.9620 96.20%
Caco-2 - 0.7704 77.04%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability - 0.5286 52.86%
Subcellular localzation Mitochondria 0.6819 68.19%
OATP2B1 inhibitior - 0.7266 72.66%
OATP1B1 inhibitior + 0.8723 87.23%
OATP1B3 inhibitior + 0.8710 87.10%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior + 0.9411 94.11%
P-glycoprotein inhibitior + 0.8229 82.29%
P-glycoprotein substrate + 0.6119 61.19%
CYP3A4 substrate + 0.7214 72.14%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8991 89.91%
CYP3A4 inhibition - 0.6767 67.67%
CYP2C9 inhibition - 0.9047 90.47%
CYP2C19 inhibition - 0.8893 88.93%
CYP2D6 inhibition - 0.9554 95.54%
CYP1A2 inhibition - 0.7438 74.38%
CYP2C8 inhibition + 0.6259 62.59%
CYP inhibitory promiscuity - 0.9296 92.96%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5891 58.91%
Eye corrosion - 0.9899 98.99%
Eye irritation - 0.9253 92.53%
Skin irritation - 0.5354 53.54%
Skin corrosion - 0.9232 92.32%
Ames mutagenesis + 0.5300 53.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6491 64.91%
Micronuclear - 0.5100 51.00%
Hepatotoxicity + 0.5608 56.08%
skin sensitisation - 0.7923 79.23%
Respiratory toxicity + 0.8444 84.44%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.8625 86.25%
Nephrotoxicity + 0.8167 81.67%
Acute Oral Toxicity (c) I 0.4534 45.34%
Estrogen receptor binding + 0.8485 84.85%
Androgen receptor binding + 0.7336 73.36%
Thyroid receptor binding + 0.5738 57.38%
Glucocorticoid receptor binding + 0.8336 83.36%
Aromatase binding + 0.7270 72.70%
PPAR gamma + 0.7598 75.98%
Honey bee toxicity - 0.6516 65.16%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5300 53.00%
Fish aquatic toxicity + 0.9893 98.93%

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
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 98.78% 85.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.06% 95.56%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 91.13% 91.07%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.11% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 90.90% 91.11%
CHEMBL2581 P07339 Cathepsin D 90.14% 98.95%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.90% 99.23%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 88.38% 97.14%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.57% 86.33%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 84.20% 94.08%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 83.52% 94.45%
CHEMBL3137262 O60341 LSD1/CoREST complex 83.47% 97.09%
CHEMBL3359 P21462 Formyl peptide receptor 1 82.69% 93.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.31% 89.00%
CHEMBL5028 O14672 ADAM10 80.85% 97.50%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.66% 94.00%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 80.59% 95.50%
CHEMBL340 P08684 Cytochrome P450 3A4 80.37% 91.19%

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.
Iochroma gesnerioides

Cross-Links

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PubChem 101664459
LOTUS LTS0046307
wikiData Q105232521