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

Details

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Internal ID cc374299-634c-4015-93db-1176a069b1b2
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
IUPAC Name (3S,5S,6R)-6-[[(3S,6aR,6bS,8aS,12aS,14bR)-4,4,6a,6b,11,11,14b-heptamethyl-8a-[(2R,3S,5S)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-hydroxy-3-[(4R)-3,4,5-trihydroxy-3-(hydroxymethyl)oxolan-2-yl]oxy-5-[(3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid
SMILES (Canonical) CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)OC6C(C(C(C(O6)C(=O)O)OC7C(C(C(O7)O)O)(CO)O)O)OC8C(C(C(CO8)O)O)O)C)C)C2C1)C)C(=O)OC9(C(C(C(C(O9)CO)O)O)O)O)C
SMILES (Isomeric) C[C@]12CC[C@@H](C(C1CC[C@@]3(C2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O[C@]6([C@H](C([C@@H](C(O6)CO)O)O)O)O)C)C)(C)C)O[C@H]7[C@H](C([C@@H](C(O7)C(=O)O)OC8C([C@H](C(O8)O)O)(CO)O)O)OC9[C@H]([C@@H]([C@@H](CO9)O)O)O
InChI InChI=1S/C52H82O24/c1-45(2)14-16-50(43(66)76-52(68)37(61)31(58)30(57)25(19-53)75-52)17-15-48(6)22(23(50)18-45)8-9-27-47(5)12-11-28(46(3,4)26(47)10-13-49(27,48)7)70-42-35(71-41-32(59)29(56)24(55)20-69-41)33(60)34(36(72-42)39(63)64)73-44-51(67,21-54)38(62)40(65)74-44/h8,23-38,40-42,44,53-62,65,67-68H,9-21H2,1-7H3,(H,63,64)/t23-,24+,25?,26?,27?,28-,29+,30+,31?,32-,33?,34-,35-,36?,37-,38-,40?,41?,42+,44?,47-,48+,49+,50-,51?,52+/m0/s1
InChI Key CHSHRZREHDMNAY-ISGYFWRUSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C52H82O24
Molecular Weight 1091.20 g/mol
Exact Mass 1090.51960348 g/mol
Topological Polar Surface Area (TPSA) 391.00 Ų
XlogP 0.30
Atomic LogP (AlogP) -2.02
H-Bond Acceptor 23
H-Bond Donor 14
Rotatable Bonds 11

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (3S,5S,6R)-6-[[(3S,6aR,6bS,8aS,12aS,14bR)-4,4,6a,6b,11,11,14b-heptamethyl-8a-[(2R,3S,5S)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-hydroxy-3-[(4R)-3,4,5-trihydroxy-3-(hydroxymethyl)oxolan-2-yl]oxy-5-[(3S,4R,5R)-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 + 0.8861 88.61%
Caco-2 - 0.8754 87.54%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability - 0.6857 68.57%
Subcellular localzation Mitochondria 0.8722 87.22%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7628 76.28%
OATP1B3 inhibitior + 0.8597 85.97%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.6250 62.50%
BSEP inhibitior + 0.8762 87.62%
P-glycoprotein inhibitior + 0.7477 74.77%
P-glycoprotein substrate + 0.5264 52.64%
CYP3A4 substrate + 0.7432 74.32%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8808 88.08%
CYP3A4 inhibition - 0.7341 73.41%
CYP2C9 inhibition - 0.8150 81.50%
CYP2C19 inhibition - 0.8949 89.49%
CYP2D6 inhibition - 0.9318 93.18%
CYP1A2 inhibition - 0.8796 87.96%
CYP2C8 inhibition + 0.7943 79.43%
CYP inhibitory promiscuity - 0.9224 92.24%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.4748 47.48%
Eye corrosion - 0.9867 98.67%
Eye irritation - 0.8999 89.99%
Skin irritation - 0.5700 57.00%
Skin corrosion - 0.9325 93.25%
Ames mutagenesis - 0.6370 63.70%
Human Ether-a-go-go-Related Gene inhibition + 0.7092 70.92%
Micronuclear - 0.7900 79.00%
Hepatotoxicity - 0.8000 80.00%
skin sensitisation - 0.8930 89.30%
Respiratory toxicity - 0.5000 50.00%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.5500 55.00%
Nephrotoxicity - 0.8378 83.78%
Acute Oral Toxicity (c) III 0.6501 65.01%
Estrogen receptor binding + 0.7544 75.44%
Androgen receptor binding + 0.7609 76.09%
Thyroid receptor binding + 0.5406 54.06%
Glucocorticoid receptor binding + 0.7607 76.07%
Aromatase binding + 0.6196 61.96%
PPAR gamma + 0.8032 80.32%
Honey bee toxicity - 0.6418 64.18%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity + 0.5500 55.00%
Fish aquatic toxicity + 0.9765 97.65%

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 96.60% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.04% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.27% 94.45%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 92.82% 95.17%
CHEMBL2581 P07339 Cathepsin D 91.73% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.99% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.64% 97.09%
CHEMBL221 P23219 Cyclooxygenase-1 88.91% 90.17%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 88.25% 95.50%
CHEMBL1994 P08235 Mineralocorticoid receptor 87.85% 100.00%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 85.97% 91.07%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.79% 86.33%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 84.92% 96.77%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.74% 95.89%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.69% 89.00%
CHEMBL5028 O14672 ADAM10 84.15% 97.50%
CHEMBL3060 Q9Y345 Glycine transporter 2 83.65% 99.17%
CHEMBL226 P30542 Adenosine A1 receptor 82.89% 95.93%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 81.93% 86.92%
CHEMBL3714130 P46095 G-protein coupled receptor 6 81.50% 97.36%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 80.88% 93.00%
CHEMBL5255 O00206 Toll-like receptor 4 80.81% 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.
Heptapleurum arboricola

Cross-Links

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PubChem 162935843
LOTUS LTS0147832
wikiData Q104959190