(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aR,10S,12aS,14aR,14bR)-10-hydroxy-8a-methoxycarbonyl-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4-dihydroxy-5-[(2R,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid

Details

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Internal ID 323eaed2-dc5e-4501-b348-505ec7168be9
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
IUPAC Name (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aR,10S,12aS,14aR,14bR)-10-hydroxy-8a-methoxycarbonyl-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4-dihydroxy-5-[(2R,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid
SMILES (Canonical) CC1(CC2C3=CCC4C5(CCC(C(C5CCC4(C3(CCC2(CC1O)C(=O)OC)C)C)(C)C)OC6C(C(C(C(O6)C(=O)O)O)O)OC7C(C(C(CO7)O)O)O)C)C
SMILES (Isomeric) C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC([C@H](C5)O)(C)C)C(=O)OC)C)C)(C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O)O[C@@H]7[C@@H]([C@H]([C@H](CO7)O)O)O
InChI InChI=1S/C42H66O14/c1-37(2)17-21-20-9-10-24-39(5)13-12-26(54-35-32(29(47)28(46)31(55-35)33(49)50)56-34-30(48)27(45)22(43)19-53-34)38(3,4)23(39)11-14-41(24,7)40(20,6)15-16-42(21,18-25(37)44)36(51)52-8/h9,21-32,34-35,43-48H,10-19H2,1-8H3,(H,49,50)/t21-,22-,23-,24+,25-,26-,27-,28-,29-,30+,31-,32+,34+,35+,39-,40+,41+,42+/m0/s1
InChI Key PEEBVTIYHLOKCL-GDHBJXCBSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C42H66O14
Molecular Weight 795.00 g/mol
Exact Mass 794.44525677 g/mol
Topological Polar Surface Area (TPSA) 222.00 Ų
XlogP 3.60
Atomic LogP (AlogP) 2.67
H-Bond Acceptor 13
H-Bond Donor 7
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aR,10S,12aS,14aR,14bR)-10-hydroxy-8a-methoxycarbonyl-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4-dihydroxy-5-[(2R,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8713 87.13%
Caco-2 - 0.8896 88.96%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.6857 68.57%
Subcellular localzation Mitochondria 0.8460 84.60%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7548 75.48%
OATP1B3 inhibitior + 0.8647 86.47%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.6000 60.00%
BSEP inhibitior - 0.5256 52.56%
P-glycoprotein inhibitior + 0.7694 76.94%
P-glycoprotein substrate - 0.6594 65.94%
CYP3A4 substrate + 0.7346 73.46%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8833 88.33%
CYP3A4 inhibition - 0.8562 85.62%
CYP2C9 inhibition - 0.8614 86.14%
CYP2C19 inhibition - 0.9174 91.74%
CYP2D6 inhibition - 0.9396 93.96%
CYP1A2 inhibition - 0.8804 88.04%
CYP2C8 inhibition + 0.7584 75.84%
CYP inhibitory promiscuity - 0.9783 97.83%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.5912 59.12%
Eye corrosion - 0.9891 98.91%
Eye irritation - 0.9109 91.09%
Skin irritation - 0.5826 58.26%
Skin corrosion - 0.9397 93.97%
Ames mutagenesis - 0.6700 67.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3860 38.60%
Micronuclear - 0.7300 73.00%
Hepatotoxicity - 0.8125 81.25%
skin sensitisation - 0.8698 86.98%
Respiratory toxicity + 0.5556 55.56%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.5625 56.25%
Nephrotoxicity - 0.8384 83.84%
Acute Oral Toxicity (c) III 0.5635 56.35%
Estrogen receptor binding + 0.7552 75.52%
Androgen receptor binding + 0.7336 73.36%
Thyroid receptor binding - 0.6518 65.18%
Glucocorticoid receptor binding + 0.6893 68.93%
Aromatase binding + 0.6739 67.39%
PPAR gamma + 0.7571 75.71%
Honey bee toxicity - 0.6895 68.95%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.5600 56.00%
Fish aquatic toxicity + 0.9632 96.32%

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 97.59% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.94% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.77% 95.56%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.45% 94.45%
CHEMBL221 P23219 Cyclooxygenase-1 89.30% 90.17%
CHEMBL3714130 P46095 G-protein coupled receptor 6 86.75% 97.36%
CHEMBL340 P08684 Cytochrome P450 3A4 85.91% 91.19%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 85.58% 94.33%
CHEMBL5028 O14672 ADAM10 84.82% 97.50%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.40% 95.89%
CHEMBL2581 P07339 Cathepsin D 83.73% 98.95%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 83.29% 96.77%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.49% 100.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 82.34% 97.09%
CHEMBL5255 O00206 Toll-like receptor 4 82.13% 92.50%

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.
Cynara cardunculus

Cross-Links

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PubChem 163024712
LOTUS LTS0248491
wikiData Q105206943