(5S,8R,9S,10S,13S,14S,16S,17R)-16-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-17-[(2S,3S,6S)-3,7-dihydroxy-6-methylheptan-2-yl]-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one

Details

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Internal ID 882ac3ff-4513-49db-a796-aab31772b56c
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
IUPAC Name (5S,8R,9S,10S,13S,14S,16S,17R)-16-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-17-[(2S,3S,6S)-3,7-dihydroxy-6-methylheptan-2-yl]-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
SMILES (Canonical) CC1C(C(C(C(O1)OC2C(C(C(OC2OC3CC4C5CCC6CC(=O)CCC6(C5CCC4(C3C(C)C(CCC(C)CO)O)C)C)CO)O)O)O)O)O
SMILES (Isomeric) C[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)O[C@@H]2[C@H]([C@H]([C@H](O[C@H]2O[C@H]3C[C@H]4[C@@H]5CC[C@H]6CC(=O)CC[C@@]6([C@H]5CC[C@@]4([C@H]3[C@H](C)[C@H](CC[C@H](C)CO)O)C)C)CO)O)O)O)O)O
InChI InChI=1S/C39H66O13/c1-18(16-40)6-9-26(43)19(2)29-27(15-25-23-8-7-21-14-22(42)10-12-38(21,4)24(23)11-13-39(25,29)5)50-37-35(33(47)31(45)28(17-41)51-37)52-36-34(48)32(46)30(44)20(3)49-36/h18-21,23-37,40-41,43-48H,6-17H2,1-5H3/t18-,19+,20-,21-,23+,24-,25-,26-,27-,28+,29-,30-,31-,32+,33-,34+,35+,36+,37+,38-,39-/m0/s1
InChI Key KXOGLUYVBNGQBQ-KDOXQQBSSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C39H66O13
Molecular Weight 742.90 g/mol
Exact Mass 742.45034216 g/mol
Topological Polar Surface Area (TPSA) 216.00 Ų
XlogP 2.20
Atomic LogP (AlogP) 1.27
H-Bond Acceptor 13
H-Bond Donor 8
Rotatable Bonds 11

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (5S,8R,9S,10S,13S,14S,16S,17R)-16-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-17-[(2S,3S,6S)-3,7-dihydroxy-6-methylheptan-2-yl]-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.5000 50.00%
Caco-2 - 0.8779 87.79%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability - 0.8000 80.00%
Subcellular localzation Mitochondria 0.7075 70.75%
OATP2B1 inhibitior - 0.5795 57.95%
OATP1B1 inhibitior + 0.8695 86.95%
OATP1B3 inhibitior + 0.9047 90.47%
MATE1 inhibitior - 0.9812 98.12%
OCT2 inhibitior - 0.6250 62.50%
BSEP inhibitior - 0.7057 70.57%
P-glycoprotein inhibitior + 0.6845 68.45%
P-glycoprotein substrate + 0.5492 54.92%
CYP3A4 substrate + 0.7338 73.38%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8533 85.33%
CYP3A4 inhibition - 0.9460 94.60%
CYP2C9 inhibition - 0.9316 93.16%
CYP2C19 inhibition - 0.9171 91.71%
CYP2D6 inhibition - 0.9651 96.51%
CYP1A2 inhibition - 0.9201 92.01%
CYP2C8 inhibition + 0.5826 58.26%
CYP inhibitory promiscuity - 0.9786 97.86%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6953 69.53%
Eye corrosion - 0.9928 99.28%
Eye irritation - 0.9232 92.32%
Skin irritation - 0.6321 63.21%
Skin corrosion - 0.9549 95.49%
Ames mutagenesis - 0.7969 79.69%
Human Ether-a-go-go-Related Gene inhibition + 0.7203 72.03%
Micronuclear - 0.9100 91.00%
Hepatotoxicity - 0.6750 67.50%
skin sensitisation - 0.9467 94.67%
Respiratory toxicity + 0.8111 81.11%
Reproductive toxicity + 0.8000 80.00%
Mitochondrial toxicity - 0.5125 51.25%
Nephrotoxicity - 0.9667 96.67%
Acute Oral Toxicity (c) I 0.6662 66.62%
Estrogen receptor binding + 0.7051 70.51%
Androgen receptor binding + 0.6793 67.93%
Thyroid receptor binding - 0.6049 60.49%
Glucocorticoid receptor binding + 0.5948 59.48%
Aromatase binding + 0.6844 68.44%
PPAR gamma + 0.6247 62.47%
Honey bee toxicity - 0.6549 65.49%
Biodegradation - 0.6500 65.00%
Crustacea aquatic toxicity - 0.6400 64.00%
Fish aquatic toxicity + 0.7852 78.52%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.32% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.92% 91.11%
CHEMBL2581 P07339 Cathepsin D 94.80% 98.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.54% 97.09%
CHEMBL6136 O60341 Lysine-specific histone demethylase 1 93.97% 95.58%
CHEMBL3714130 P46095 G-protein coupled receptor 6 92.72% 97.36%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 91.14% 95.89%
CHEMBL1994 P08235 Mineralocorticoid receptor 90.85% 100.00%
CHEMBL226 P30542 Adenosine A1 receptor 90.67% 95.93%
CHEMBL253 P34972 Cannabinoid CB2 receptor 90.24% 97.25%
CHEMBL2094135 Q96BI3 Gamma-secretase 90.11% 98.05%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.96% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.17% 86.33%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 85.87% 97.33%
CHEMBL1871 P10275 Androgen Receptor 84.61% 96.43%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.47% 95.89%
CHEMBL2842 P42345 Serine/threonine-protein kinase mTOR 84.33% 92.78%
CHEMBL237 P41145 Kappa opioid receptor 84.32% 98.10%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 83.77% 90.71%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 83.03% 91.24%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 82.95% 100.00%
CHEMBL3359 P21462 Formyl peptide receptor 1 82.73% 93.56%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 82.39% 95.83%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 81.85% 100.00%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 81.43% 96.38%
CHEMBL4105786 P41182 B-cell lymphoma 6 protein 80.50% 92.86%
CHEMBL4227 P25090 Lipoxin A4 receptor 80.32% 100.00%

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.
Tribulus cistoides

Cross-Links

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PubChem 162847999
LOTUS LTS0243867
wikiData Q105147432