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1-[(3S,5S,8S,9R,10R,12R,13R,14R,17S)-5,8,14,17-tetrahydroxy-3-[(2R,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,4R,5R,6R)-5-[(2S,3R,4S,5R,6R)-3-hydroxy-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-12-[(E)-3-phenylprop-2-enoyl]oxy-2,3,4,9,11,12,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl benzoate

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 182189a6-5aac-4734-bbd3-5ce1395dfa1f
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
IUPAC Name 1-[(3S,5S,8S,9R,10R,12R,13R,14R,17S)-5,8,14,17-tetrahydroxy-3-[(2R,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,4R,5R,6R)-5-[(2S,3R,4S,5R,6R)-3-hydroxy-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-12-[(E)-3-phenylprop-2-enoyl]oxy-2,3,4,9,11,12,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl benzoate
SMILES (Canonical) CC1C(C(CC(O1)OC2CCC3(C4CC(C5(C(CCC5(C4(C=CC3(C2)O)O)O)(C(C)OC(=O)C6=CC=CC=C6)O)C)OC(=O)C=CC7=CC=CC=C7)C)OC)OC8CC(C(C(O8)C)OC9CC(C(C(O9)C)OC1C(C(C(C(O1)C)OC1C(C(C(C(O1)CO)O)O)O)OC)O)OC)OC
SMILES (Isomeric) C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2CC[C@@]3([C@H]4C[C@H]([C@@]5([C@@](CC[C@@]5([C@@]4(C=C[C@]3(C2)O)O)O)(C(C)OC(=O)C6=CC=CC=C6)O)C)OC(=O)/C=C/C7=CC=CC=C7)C)OC)O[C@H]8C[C@@H]([C@@H]([C@H](O8)C)O[C@H]9C[C@H]([C@@H]([C@H](O9)C)O[C@H]1[C@@H]([C@@H]([C@@H]([C@H](O1)C)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)OC)O)OC)OC
InChI InChI=1S/C71H102O27/c1-36-58(95-52-31-45(84-9)59(37(2)88-52)96-53-32-46(85-10)60(38(3)89-53)97-65-57(77)62(86-11)61(39(4)90-65)98-64-56(76)55(75)54(74)47(35-72)93-64)44(83-8)30-51(87-36)92-43-24-25-66(6)48-33-49(94-50(73)23-22-41-18-14-12-15-19-41)67(7)69(80,40(5)91-63(78)42-20-16-13-17-21-42)28-29-71(67,82)70(48,81)27-26-68(66,79)34-43/h12-23,26-27,36-40,43-49,51-62,64-65,72,74-77,79-82H,24-25,28-35H2,1-11H3/b23-22+/t36-,37-,38-,39-,40?,43+,44+,45+,46-,47-,48-,49-,51+,52+,53+,54-,55+,56-,57-,58-,59-,60-,61-,62+,64+,65+,66-,67-,68-,69-,70+,71-/m1/s1
InChI Key ATSQTDGTTSBCIO-KDBYNGFGSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C71H102O27
Molecular Weight 1387.50 g/mol
Exact Mass 1386.66084797 g/mol
Topological Polar Surface Area (TPSA) 364.00 Ų
XlogP 2.70
Atomic LogP (AlogP) 2.66
H-Bond Acceptor 27
H-Bond Donor 9
Rotatable Bonds 21

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 1-[(3S,5S,8S,9R,10R,12R,13R,14R,17S)-5,8,14,17-tetrahydroxy-3-[(2R,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,4R,5R,6R)-5-[(2S,3R,4S,5R,6R)-3-hydroxy-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-12-[(E)-3-phenylprop-2-enoyl]oxy-2,3,4,9,11,12,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl benzoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6693 66.93%
Caco-2 - 0.8586 85.86%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.8571 85.71%
Subcellular localzation Mitochondria 0.7281 72.81%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8126 81.26%
OATP1B3 inhibitior + 0.8952 89.52%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.7000 70.00%
BSEP inhibitior + 0.9798 97.98%
P-glycoprotein inhibitior + 0.7436 74.36%
P-glycoprotein substrate + 0.7700 77.00%
CYP3A4 substrate + 0.7463 74.63%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8853 88.53%
CYP3A4 inhibition - 0.7290 72.90%
CYP2C9 inhibition - 0.9220 92.20%
CYP2C19 inhibition - 0.9292 92.92%
CYP2D6 inhibition - 0.9558 95.58%
CYP1A2 inhibition - 0.9008 90.08%
CYP2C8 inhibition + 0.8226 82.26%
CYP inhibitory promiscuity - 0.9629 96.29%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6681 66.81%
Eye corrosion - 0.9923 99.23%
Eye irritation - 0.8966 89.66%
Skin irritation - 0.6509 65.09%
Skin corrosion - 0.9479 94.79%
Ames mutagenesis - 0.6540 65.40%
Human Ether-a-go-go-Related Gene inhibition + 0.7995 79.95%
Micronuclear - 0.7500 75.00%
Hepatotoxicity - 0.6137 61.37%
skin sensitisation - 0.9343 93.43%
Respiratory toxicity + 0.6778 67.78%
Reproductive toxicity + 0.8556 85.56%
Mitochondrial toxicity + 0.7125 71.25%
Nephrotoxicity - 0.9832 98.32%
Acute Oral Toxicity (c) I 0.5692 56.92%
Estrogen receptor binding + 0.6711 67.11%
Androgen receptor binding + 0.7679 76.79%
Thyroid receptor binding + 0.7497 74.97%
Glucocorticoid receptor binding + 0.8136 81.36%
Aromatase binding + 0.6846 68.46%
PPAR gamma + 0.8117 81.17%
Honey bee toxicity - 0.6371 63.71%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity + 0.5745 57.45%
Fish aquatic toxicity + 0.9742 97.42%

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 98.87% 91.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 98.50% 86.33%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 97.20% 96.00%
CHEMBL4302 P08183 P-glycoprotein 1 96.86% 92.98%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.66% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.77% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.40% 95.56%
CHEMBL226 P30542 Adenosine A1 receptor 93.93% 95.93%
CHEMBL2716 Q8WUI4 Histone deacetylase 7 91.49% 89.44%
CHEMBL2581 P07339 Cathepsin D 90.96% 98.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 90.50% 89.00%
CHEMBL221 P23219 Cyclooxygenase-1 90.34% 90.17%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 90.10% 94.23%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 89.10% 95.17%
CHEMBL5028 O14672 ADAM10 88.35% 97.50%
CHEMBL3475 P05121 Plasminogen activator inhibitor-1 87.64% 83.00%
CHEMBL4227 P25090 Lipoxin A4 receptor 87.60% 100.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.40% 95.89%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 86.83% 95.50%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 85.17% 95.89%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 84.65% 93.00%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 84.44% 92.62%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.70% 100.00%
CHEMBL3714130 P46095 G-protein coupled receptor 6 83.06% 97.36%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 82.78% 100.00%
CHEMBL3359 P21462 Formyl peptide receptor 1 82.68% 93.56%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 82.14% 99.23%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 82.11% 97.14%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 81.79% 96.47%
CHEMBL3060 Q9Y345 Glycine transporter 2 81.35% 99.17%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 81.25% 94.08%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 80.06% 94.62%

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.
Gymnema sylvestre

Cross-Links

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PubChem 101948684
LOTUS LTS0028772
wikiData Q104918663