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(2S,3R,4S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-3-[(2R,3R,4S,5R,6R)-4-[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylic 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 b703f9a1-8dd1-4364-b13c-21e66008ec71
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
IUPAC Name (2S,3R,4S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-3-[(2R,3R,4S,5R,6R)-4-[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylic acid
SMILES (Canonical) CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CC(C(C5(C)C(=O)O)OC6C(C(C(C(O6)CO)O)OC7C(C(C(C(O7)C(=O)O)O)O)O)O)O)C)C)C2C1)C)C(=O)O)C
SMILES (Isomeric) C[C@@]12CC[C@@H]3[C@@]([C@H]1CC=C4[C@]2(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O)C)(C[C@@H]([C@@H]([C@@]3(C)C(=O)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)C(=O)O)O)O)O)O)O)C
InChI InChI=1S/C42H64O17/c1-37(2)11-13-42(36(54)55)14-12-39(4)18(19(42)15-37)7-8-22-38(3)16-20(44)31(41(6,35(52)53)23(38)9-10-40(22,39)5)59-34-28(49)29(24(45)21(17-43)56-34)57-33-27(48)25(46)26(47)30(58-33)32(50)51/h7,19-31,33-34,43-49H,8-17H2,1-6H3,(H,50,51)(H,52,53)(H,54,55)/t19-,20-,21+,22+,23+,24+,25-,26-,27+,28+,29-,30-,31-,33+,34-,38+,39+,40+,41-,42-/m0/s1
InChI Key UPPFQELNOOICNS-WCWMROHNSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C42H64O17
Molecular Weight 840.90 g/mol
Exact Mass 840.41435057 g/mol
Topological Polar Surface Area (TPSA) 290.00 Ų
XlogP 2.30
Atomic LogP (AlogP) 1.01
H-Bond Acceptor 14
H-Bond Donor 10
Rotatable Bonds 8

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2S,3R,4S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-3-[(2R,3R,4S,5R,6R)-4-[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8283 82.83%
Caco-2 - 0.8863 88.63%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.8143 81.43%
Subcellular localzation Mitochondria 0.8738 87.38%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7971 79.71%
OATP1B3 inhibitior - 0.4240 42.40%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.5026 50.26%
BSEP inhibitior - 0.4891 48.91%
P-glycoprotein inhibitior + 0.7476 74.76%
P-glycoprotein substrate - 0.6995 69.95%
CYP3A4 substrate + 0.6949 69.49%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8798 87.98%
CYP3A4 inhibition - 0.7325 73.25%
CYP2C9 inhibition - 0.8442 84.42%
CYP2C19 inhibition - 0.9307 93.07%
CYP2D6 inhibition - 0.9491 94.91%
CYP1A2 inhibition - 0.8849 88.49%
CYP2C8 inhibition + 0.6971 69.71%
CYP inhibitory promiscuity - 0.9622 96.22%
UGT catelyzed - 0.8000 80.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6162 61.62%
Eye corrosion - 0.9902 99.02%
Eye irritation - 0.9083 90.83%
Skin irritation - 0.5231 52.31%
Skin corrosion - 0.9438 94.38%
Ames mutagenesis - 0.9300 93.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3742 37.42%
Micronuclear - 0.7600 76.00%
Hepatotoxicity - 0.8592 85.92%
skin sensitisation - 0.9055 90.55%
Respiratory toxicity + 0.5222 52.22%
Reproductive toxicity + 0.9222 92.22%
Mitochondrial toxicity - 0.5375 53.75%
Nephrotoxicity + 0.4506 45.06%
Acute Oral Toxicity (c) III 0.7819 78.19%
Estrogen receptor binding + 0.7890 78.90%
Androgen receptor binding + 0.7440 74.40%
Thyroid receptor binding - 0.6644 66.44%
Glucocorticoid receptor binding + 0.6880 68.80%
Aromatase binding + 0.6252 62.52%
PPAR gamma + 0.7610 76.10%
Honey bee toxicity - 0.7502 75.02%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.6200 62.00%
Fish aquatic toxicity + 0.9670 96.70%

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 98.92% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.87% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.45% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.04% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.13% 97.09%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 89.92% 95.17%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.79% 86.33%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 85.37% 93.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.87% 95.89%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 83.71% 95.50%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 83.11% 92.62%
CHEMBL3714130 P46095 G-protein coupled receptor 6 82.93% 97.36%
CHEMBL5255 O00206 Toll-like receptor 4 81.46% 92.50%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.05% 100.00%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 80.41% 94.33%

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.
Lindernia procumbens

Cross-Links

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PubChem 101682245
LOTUS LTS0212499
wikiData Q105276926