(2R)-2-[(3R,8S,9R,10S,13R,14S,16R,17R)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-16-hydroxy-4,4,9,13,14-pentamethyl-11-oxo-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-5-(2-hydroxypropan-2-yl)-2-methylfuran-3-one

Details

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Internal ID 21c113d3-8654-40ab-84e2-8456d922e884
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
IUPAC Name (2R)-2-[(3R,8S,9R,10S,13R,14S,16R,17R)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-16-hydroxy-4,4,9,13,14-pentamethyl-11-oxo-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-5-(2-hydroxypropan-2-yl)-2-methylfuran-3-one
SMILES (Canonical) CC1C(C(C(C(O1)OC2C(C(C(OC2OC3CCC4C(=CCC5C4(C(=O)CC6(C5(CC(C6C7(C(=O)C=C(O7)C(C)(C)O)C)O)C)C)C)C3(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]3CC[C@H]4C(=CC[C@@H]5[C@]4(C(=O)C[C@]6([C@]5(C[C@H]([C@@H]6[C@@]7(C(=O)C=C(O7)C(C)(C)O)C)O)C)C)C)C3(C)C)CO)O)O)O)O)O
InChI InChI=1S/C42H64O15/c1-18-28(47)30(49)32(51)35(53-18)56-33-31(50)29(48)22(17-43)54-36(33)55-26-13-11-20-19(37(26,2)3)10-12-23-39(6)15-21(44)34(40(39,7)16-25(46)41(20,23)8)42(9)24(45)14-27(57-42)38(4,5)52/h10,14,18,20-23,26,28-36,43-44,47-52H,11-13,15-17H2,1-9H3/t18-,20-,21+,22+,23-,26+,28-,29+,30+,31-,32+,33+,34-,35-,36-,39-,40+,41-,42-/m0/s1
InChI Key FNNCXDZYMORRHA-KCXVRDEASA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C42H64O15
Molecular Weight 808.90 g/mol
Exact Mass 808.42452133 g/mol
Topological Polar Surface Area (TPSA) 242.00 Ų
XlogP 0.00
Atomic LogP (AlogP) 0.79
H-Bond Acceptor 15
H-Bond Donor 8
Rotatable Bonds 7

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2R)-2-[(3R,8S,9R,10S,13R,14S,16R,17R)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-16-hydroxy-4,4,9,13,14-pentamethyl-11-oxo-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-5-(2-hydroxypropan-2-yl)-2-methylfuran-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 + 0.9168 91.68%
Caco-2 - 0.8762 87.62%
Blood Brain Barrier - 0.5750 57.50%
Human oral bioavailability - 0.8714 87.14%
Subcellular localzation Mitochondria 0.8881 88.81%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8300 83.00%
OATP1B3 inhibitior + 0.8879 88.79%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.8250 82.50%
BSEP inhibitior - 0.5381 53.81%
P-glycoprotein inhibitior + 0.7510 75.10%
P-glycoprotein substrate + 0.5732 57.32%
CYP3A4 substrate + 0.7344 73.44%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8798 87.98%
CYP3A4 inhibition - 0.6811 68.11%
CYP2C9 inhibition - 0.8073 80.73%
CYP2C19 inhibition - 0.9331 93.31%
CYP2D6 inhibition - 0.9408 94.08%
CYP1A2 inhibition - 0.9182 91.82%
CYP2C8 inhibition + 0.6999 69.99%
CYP inhibitory promiscuity - 0.9095 90.95%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.4803 48.03%
Eye corrosion - 0.9887 98.87%
Eye irritation - 0.9098 90.98%
Skin irritation + 0.5206 52.06%
Skin corrosion - 0.9353 93.53%
Ames mutagenesis - 0.7400 74.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7257 72.57%
Micronuclear - 0.7500 75.00%
Hepatotoxicity - 0.7153 71.53%
skin sensitisation - 0.9137 91.37%
Respiratory toxicity + 0.6000 60.00%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.6375 63.75%
Nephrotoxicity - 0.7857 78.57%
Acute Oral Toxicity (c) I 0.6513 65.13%
Estrogen receptor binding + 0.7439 74.39%
Androgen receptor binding + 0.7598 75.98%
Thyroid receptor binding - 0.5075 50.75%
Glucocorticoid receptor binding + 0.7411 74.11%
Aromatase binding + 0.6689 66.89%
PPAR gamma + 0.7522 75.22%
Honey bee toxicity - 0.6781 67.81%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity + 0.5200 52.00%
Fish aquatic toxicity + 0.9802 98.02%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.80% 91.11%
CHEMBL2581 P07339 Cathepsin D 96.46% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.49% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.64% 86.33%
CHEMBL218 P21554 Cannabinoid CB1 receptor 92.83% 96.61%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.26% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.72% 95.56%
CHEMBL226 P30542 Adenosine A1 receptor 90.68% 95.93%
CHEMBL3714130 P46095 G-protein coupled receptor 6 90.68% 97.36%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 90.44% 85.14%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.78% 89.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 89.47% 94.00%
CHEMBL1937 Q92769 Histone deacetylase 2 89.12% 94.75%
CHEMBL253 P34972 Cannabinoid CB2 receptor 88.84% 97.25%
CHEMBL3401 O75469 Pregnane X receptor 86.59% 94.73%
CHEMBL1994 P08235 Mineralocorticoid receptor 86.48% 100.00%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 85.27% 97.33%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 84.09% 86.92%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 83.85% 97.14%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 82.62% 93.04%
CHEMBL4829 O00763 Acetyl-CoA carboxylase 2 82.58% 98.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.25% 95.89%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 81.97% 91.07%
CHEMBL241 Q14432 Phosphodiesterase 3A 81.90% 92.94%
CHEMBL5255 O00206 Toll-like receptor 4 81.61% 92.50%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 81.56% 96.21%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 80.58% 100.00%
CHEMBL3359 P21462 Formyl peptide receptor 1 80.49% 93.56%
CHEMBL4208 P20618 Proteasome component C5 80.32% 90.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.07% 99.23%

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.
Picria fel-terrae

Cross-Links

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PubChem 101711553
LOTUS LTS0261571
wikiData Q104998386