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(1R,2S,4S,5R,10R,11S,13S,14R,15R,17R,18S)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-5,13,17-trihydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one

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 92c89ae8-7f13-4249-8156-6a6328d838cc
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (1R,2S,4S,5R,10R,11S,13S,14R,15R,17R,18S)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-5,13,17-trihydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(C)C2CC(C3C2(C(CC4C3C5C(O5)C6(C4(C(=O)C=CC6)C)O)O)C)O)C
SMILES (Isomeric) CC1=C(C(=O)O[C@H](C1)[C@@H](C)[C@H]2C[C@H]([C@@H]3[C@@]2([C@H](C[C@H]4[C@H]3[C@H]5[C@H](O5)[C@@]6([C@@]4(C(=O)C=CC6)C)O)O)C)O)C
InChI InChI=1S/C28H38O7/c1-12-9-18(34-25(32)13(12)2)14(3)15-10-17(29)22-21-16(11-20(31)26(15,22)4)27(5)19(30)7-6-8-28(27,33)24-23(21)35-24/h6-7,14-18,20-24,29,31,33H,8-11H2,1-5H3/t14-,15+,16-,17+,18+,20-,21+,22-,23-,24-,26-,27-,28-/m0/s1
InChI Key PXNLYJYFBSKVBN-QXWXSVGDSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C28H38O7
Molecular Weight 486.60 g/mol
Exact Mass 486.26175355 g/mol
Topological Polar Surface Area (TPSA) 117.00 Ų
XlogP 2.00
Atomic LogP (AlogP) 2.32
H-Bond Acceptor 7
H-Bond Donor 3
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1R,2S,4S,5R,10R,11S,13S,14R,15R,17R,18S)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-5,13,17-trihydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9611 96.11%
Caco-2 - 0.6970 69.70%
Blood Brain Barrier + 0.5750 57.50%
Human oral bioavailability - 0.7714 77.14%
Subcellular localzation Mitochondria 0.5555 55.55%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8638 86.38%
OATP1B3 inhibitior + 0.9623 96.23%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.8931 89.31%
P-glycoprotein inhibitior + 0.6214 62.14%
P-glycoprotein substrate + 0.6480 64.80%
CYP3A4 substrate + 0.6975 69.75%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9032 90.32%
CYP3A4 inhibition - 0.7256 72.56%
CYP2C9 inhibition - 0.9112 91.12%
CYP2C19 inhibition - 0.9120 91.20%
CYP2D6 inhibition - 0.9499 94.99%
CYP1A2 inhibition - 0.8517 85.17%
CYP2C8 inhibition - 0.5704 57.04%
CYP inhibitory promiscuity - 0.9565 95.65%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.4978 49.78%
Eye corrosion - 0.9902 99.02%
Eye irritation - 0.9541 95.41%
Skin irritation + 0.5124 51.24%
Skin corrosion - 0.8970 89.70%
Ames mutagenesis - 0.6219 62.19%
Human Ether-a-go-go-Related Gene inhibition + 0.7308 73.08%
Micronuclear - 0.5500 55.00%
Hepatotoxicity - 0.5290 52.90%
skin sensitisation - 0.7787 77.87%
Respiratory toxicity + 0.7778 77.78%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.9250 92.50%
Nephrotoxicity + 0.7835 78.35%
Acute Oral Toxicity (c) I 0.6437 64.37%
Estrogen receptor binding + 0.7990 79.90%
Androgen receptor binding + 0.7099 70.99%
Thyroid receptor binding + 0.5701 57.01%
Glucocorticoid receptor binding + 0.6346 63.46%
Aromatase binding + 0.6468 64.68%
PPAR gamma + 0.6655 66.55%
Honey bee toxicity - 0.7262 72.62%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5300 53.00%
Fish aquatic toxicity + 0.9596 95.96%

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 99.19% 85.14%
CHEMBL4040 P28482 MAP kinase ERK2 95.47% 83.82%
CHEMBL253 P34972 Cannabinoid CB2 receptor 94.46% 97.25%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.46% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.08% 86.33%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 91.19% 91.11%
CHEMBL220 P22303 Acetylcholinesterase 90.85% 94.45%
CHEMBL1806 P11388 DNA topoisomerase II alpha 90.22% 89.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 90.00% 100.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 89.76% 99.23%
CHEMBL2581 P07339 Cathepsin D 89.26% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 88.45% 96.09%
CHEMBL2996 Q05655 Protein kinase C delta 87.07% 97.79%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 86.01% 97.21%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 85.72% 97.14%
CHEMBL3137262 O60341 LSD1/CoREST complex 83.33% 97.09%
CHEMBL3401 O75469 Pregnane X receptor 82.41% 94.73%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 81.92% 90.71%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.85% 95.89%

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.
Datura ferox

Cross-Links

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PubChem 162927735
LOTUS LTS0160931
wikiData Q105216281