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

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 9c383767-e423-4cb1-9ab4-ef390e1afc3f
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
IUPAC Name (2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-[(2S,3R,4R,5S,6R)-5-[(2S,3R,4S,5R,6S)-5-[(2S,3R,4S,5R)-3,5-dihydroxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-3-hydroxy-6-methyl-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxycarbonyl-4-formyl-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-hydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid
SMILES (Canonical) CC1C(C(C(C(O1)OC2C(C(OC(C2OC3C(C(C(C(O3)C)OC4C(C(C(CO4)O)OC5C(C(C(CO5)O)O)O)O)O)O)C)OC(=O)C67CCC(CC6C8=CCC9C1(CCC(C(C1CCC9(C8(CC7)C)C)(C)C=O)OC1C(C(C(C(O1)C(=O)O)O)OC1C(C(C(CO1)O)O)O)OC1C(C(C(C(O1)CO)O)O)O)C)(C)C)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](O[C@@H]([C@@H]2O[C@H]3[C@@H]([C@@H]([C@H]([C@@H](O3)C)O[C@H]4[C@@H]([C@H]([C@@H](CO4)O)O[C@H]5[C@@H]([C@H]([C@@H](CO5)O)O)O)O)O)O)C)OC(=O)[C@@]67CC[C@@]8(C(=CC[C@H]9[C@]8(CC[C@@H]1[C@@]9(CC[C@@H]([C@@]1(C)C=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)C(=O)O)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)O[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O)C)C)[C@@H]6CC(CC7)(C)C)C)O)O)O)O
InChI InChI=1S/C75H118O39/c1-26-38(81)42(85)47(90)64(102-26)111-57-52(95)67(104-28(3)54(57)108-65-49(92)44(87)53(27(2)103-65)107-63-51(94)55(33(80)24-101-63)109-61-45(88)39(82)31(78)22-99-61)114-69(98)75-18-16-70(4,5)20-30(75)29-10-11-36-71(6)14-13-37(72(7,25-77)35(71)12-15-74(36,9)73(29,8)17-19-75)106-68-59(113-66-48(91)43(86)41(84)34(21-76)105-66)56(50(93)58(112-68)60(96)97)110-62-46(89)40(83)32(79)23-100-62/h10,25-28,30-59,61-68,76,78-95H,11-24H2,1-9H3,(H,96,97)/t26-,27-,28+,30-,31+,32+,33+,34+,35+,36+,37-,38-,39-,40-,41-,42+,43-,44-,45+,46+,47+,48+,49+,50-,51+,52+,53-,54-,55-,56-,57+,58-,59+,61-,62-,63-,64-,65-,66-,67-,68+,71-,72-,73+,74+,75-/m0/s1
InChI Key PHKMXPRTJWCJJJ-KAUSCZHPSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C75H118O39
Molecular Weight 1643.70 g/mol
Exact Mass 1642.7250239 g/mol
Topological Polar Surface Area (TPSA) 604.00 Ų
XlogP -4.90
Atomic LogP (AlogP) -6.47
H-Bond Acceptor 38
H-Bond Donor 20
Rotatable Bonds 19

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,4S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-[(2S,3R,4R,5S,6R)-5-[(2S,3R,4S,5R,6S)-5-[(2S,3R,4S,5R)-3,5-dihydroxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-3-hydroxy-6-methyl-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxycarbonyl-4-formyl-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-hydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2S,3R,4S,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 + 0.7601 76.01%
Caco-2 - 0.8614 86.14%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.8143 81.43%
Subcellular localzation Mitochondria 0.8703 87.03%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7345 73.45%
OATP1B3 inhibitior - 0.4610 46.10%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.5026 50.26%
BSEP inhibitior + 0.9590 95.90%
P-glycoprotein inhibitior + 0.7431 74.31%
P-glycoprotein substrate + 0.5462 54.62%
CYP3A4 substrate + 0.7391 73.91%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8749 87.49%
CYP3A4 inhibition - 0.8310 83.10%
CYP2C9 inhibition - 0.8704 87.04%
CYP2C19 inhibition - 0.9216 92.16%
CYP2D6 inhibition - 0.9491 94.91%
CYP1A2 inhibition - 0.9009 90.09%
CYP2C8 inhibition + 0.7877 78.77%
CYP inhibitory promiscuity - 0.9733 97.33%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6024 60.24%
Eye corrosion - 0.9896 98.96%
Eye irritation - 0.8964 89.64%
Skin irritation - 0.5876 58.76%
Skin corrosion - 0.9441 94.41%
Ames mutagenesis - 0.6500 65.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7852 78.52%
Micronuclear - 0.7800 78.00%
Hepatotoxicity - 0.9250 92.50%
skin sensitisation - 0.9013 90.13%
Respiratory toxicity - 0.5444 54.44%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity - 0.6250 62.50%
Nephrotoxicity - 0.9650 96.50%
Acute Oral Toxicity (c) III 0.8023 80.23%
Estrogen receptor binding + 0.6389 63.89%
Androgen receptor binding + 0.7534 75.34%
Thyroid receptor binding + 0.7290 72.90%
Glucocorticoid receptor binding + 0.8201 82.01%
Aromatase binding + 0.6975 69.75%
PPAR gamma + 0.8202 82.02%
Honey bee toxicity - 0.6486 64.86%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.5455 54.55%
Fish aquatic toxicity + 0.9585 95.85%

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 98.10% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.44% 96.09%
CHEMBL3714130 P46095 G-protein coupled receptor 6 92.12% 97.36%
CHEMBL2581 P07339 Cathepsin D 91.98% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.47% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.19% 95.56%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.72% 94.45%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.25% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.10% 89.00%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 86.31% 93.00%
CHEMBL226 P30542 Adenosine A1 receptor 85.22% 95.93%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 84.39% 95.50%
CHEMBL3060 Q9Y345 Glycine transporter 2 84.14% 99.17%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 83.11% 86.92%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.10% 100.00%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 82.76% 96.77%
CHEMBL4302 P08183 P-glycoprotein 1 82.22% 92.98%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 80.46% 95.17%
CHEMBL221 P23219 Cyclooxygenase-1 80.45% 90.17%

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.
Acanthophyllum squarrosum

Cross-Links

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PubChem 44558934
LOTUS LTS0017947
wikiData Q105209022