methyl (2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-9-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-5-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxyoxane-2-carboxylate

Details

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Internal ID 0d651195-4aff-4097-b594-2c0a26443ac0
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
IUPAC Name methyl (2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-9-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-5-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxyoxane-2-carboxylate
SMILES (Canonical) CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(C(OC3OC4CCC5(C(C4(C)CO)CCC6(C5CC=C7C6(CCC8(C7CC(CC8O)(C)C)C)C)C)C)C(=O)OC)O)O)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]3[C@H]([C@@H]([C@H](O[C@H]3O[C@H]4CC[C@]5([C@H]([C@@]4(C)CO)CC[C@@]6([C@@H]5CC=C7[C@]6(CC[C@@]8([C@H]7CC(C[C@H]8O)(C)C)C)C)C)C)C(=O)OC)O)O)CO)O)O)O)O)O
InChI InChI=1S/C49H80O18/c1-22-30(53)32(55)36(59)41(62-22)66-38-33(56)31(54)25(20-50)63-42(38)67-39-35(58)34(57)37(40(60)61-9)65-43(39)64-29-13-14-46(5)26(47(29,6)21-51)12-15-49(8)27(46)11-10-23-24-18-44(2,3)19-28(52)45(24,4)16-17-48(23,49)7/h10,22,24-39,41-43,50-59H,11-21H2,1-9H3/t22-,24-,25+,26+,27+,28+,29-,30-,31-,32+,33-,34-,35-,36+,37-,38+,39+,41-,42-,43+,45+,46-,47+,48+,49+/m0/s1
InChI Key ZEIAROWTCSYWFT-QVOSIWNASA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C49H80O18
Molecular Weight 957.10 g/mol
Exact Mass 956.53446570 g/mol
Topological Polar Surface Area (TPSA) 284.00 Ų
XlogP 2.70
Atomic LogP (AlogP) 0.79
H-Bond Acceptor 18
H-Bond Donor 10
Rotatable Bonds 9

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl (2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-9-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-5-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxyoxane-2-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7768 77.68%
Caco-2 - 0.9248 92.48%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability - 0.8286 82.86%
Subcellular localzation Mitochondria 0.8363 83.63%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8399 83.99%
OATP1B3 inhibitior - 0.4203 42.03%
MATE1 inhibitior - 0.9812 98.12%
OCT2 inhibitior - 0.6750 67.50%
BSEP inhibitior + 0.8336 83.36%
P-glycoprotein inhibitior + 0.7573 75.73%
P-glycoprotein substrate - 0.5894 58.94%
CYP3A4 substrate + 0.7334 73.34%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8776 87.76%
CYP3A4 inhibition - 0.9376 93.76%
CYP2C9 inhibition - 0.8801 88.01%
CYP2C19 inhibition - 0.8916 89.16%
CYP2D6 inhibition - 0.9410 94.10%
CYP1A2 inhibition - 0.8965 89.65%
CYP2C8 inhibition + 0.7411 74.11%
CYP inhibitory promiscuity - 0.9714 97.14%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6190 61.90%
Eye corrosion - 0.9892 98.92%
Eye irritation - 0.9066 90.66%
Skin irritation - 0.6475 64.75%
Skin corrosion - 0.9466 94.66%
Ames mutagenesis - 0.8700 87.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7735 77.35%
Micronuclear - 0.8400 84.00%
Hepatotoxicity - 0.8250 82.50%
skin sensitisation - 0.8860 88.60%
Respiratory toxicity - 0.6556 65.56%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity - 0.7500 75.00%
Nephrotoxicity - 0.6838 68.38%
Acute Oral Toxicity (c) III 0.7315 73.15%
Estrogen receptor binding + 0.8028 80.28%
Androgen receptor binding + 0.7370 73.70%
Thyroid receptor binding - 0.5881 58.81%
Glucocorticoid receptor binding + 0.6974 69.74%
Aromatase binding + 0.6544 65.44%
PPAR gamma + 0.7910 79.10%
Honey bee toxicity - 0.6933 69.33%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.5800 58.00%
Fish aquatic toxicity + 0.8930 89.30%

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 97.49% 91.11%
CHEMBL3714130 P46095 G-protein coupled receptor 6 96.32% 97.36%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.35% 96.09%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 87.68% 94.33%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.17% 97.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 86.59% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.03% 95.56%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 85.78% 91.07%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.74% 95.89%
CHEMBL218 P21554 Cannabinoid CB1 receptor 84.35% 96.61%
CHEMBL253 P34972 Cannabinoid CB2 receptor 84.13% 97.25%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.09% 100.00%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 84.04% 95.50%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.70% 86.33%
CHEMBL3060 Q9Y345 Glycine transporter 2 82.98% 99.17%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 82.37% 93.00%
CHEMBL3401 O75469 Pregnane X receptor 81.16% 94.73%
CHEMBL221 P23219 Cyclooxygenase-1 80.89% 90.17%
CHEMBL2581 P07339 Cathepsin D 80.75% 98.95%
CHEMBL5028 O14672 ADAM10 80.64% 97.50%
CHEMBL2782 P35610 Acyl coenzyme A:cholesterol acyltransferase 1 80.57% 91.65%
CHEMBL1806 P11388 DNA topoisomerase II alpha 80.18% 89.00%

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.
Impatiens siculifera
Phyllolobium chinense

Cross-Links

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PubChem 21629875
LOTUS LTS0274574
wikiData Q104400442