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

Details

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Internal ID 5e0d06a3-6285-410f-85fd-ce11c8e57463
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
IUPAC Name (2S,3S,4S,5R,6R)-6-[[(3S,4R,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-(2-methylbut-2-enoyloxy)-9-[(Z)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-4-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid
SMILES (Canonical) CC=C(C)C(=O)OC1C(C2(C(CC1(C)C)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)CO)OC6C(C(C(C(O6)C(=O)O)O)OC7C(C(C(CO7)O)O)O)O)C)CO)OC(=O)C(=CC)C
SMILES (Isomeric) C/C=C(/C)\C(=O)O[C@H]1[C@@H](C(C[C@@H]2[C@]1([C@@H](C[C@@]3(C2=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H]([C@@]5(C)CO)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O[C@H]7[C@@H]([C@H]([C@H](CO7)O)O)O)O)C)C)C)O)CO)(C)C)OC(=O)C(=CC)C
InChI InChI=1S/C51H78O18/c1-11-24(3)42(62)68-39-40(69-43(63)25(4)12-2)51(23-53)27(19-46(39,5)6)26-13-14-30-47(7)17-16-32(48(8,22-52)29(47)15-18-49(30,9)50(26,10)20-31(51)55)65-45-36(59)37(35(58)38(67-45)41(60)61)66-44-34(57)33(56)28(54)21-64-44/h11-13,27-40,44-45,52-59H,14-23H2,1-10H3,(H,60,61)/b24-11?,25-12-/t27-,28-,29+,30+,31+,32-,33-,34+,35-,36+,37-,38-,39-,40-,44-,45+,47-,48-,49+,50+,51-/m0/s1
InChI Key WGPUVZRQQKVFDP-QLHFFUEASA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C51H78O18
Molecular Weight 979.20 g/mol
Exact Mass 978.51881563 g/mol
Topological Polar Surface Area (TPSA) 289.00 Ų
XlogP 4.10
Atomic LogP (AlogP) 2.44
H-Bond Acceptor 17
H-Bond Donor 9
Rotatable Bonds 11

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,4R,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-(2-methylbut-2-enoyloxy)-9-[(Z)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-4-[(2S,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 + 0.7601 76.01%
Caco-2 - 0.8684 86.84%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.6857 68.57%
Subcellular localzation Mitochondria 0.8703 87.03%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8173 81.73%
OATP1B3 inhibitior - 0.4610 46.10%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.5026 50.26%
BSEP inhibitior + 0.9372 93.72%
P-glycoprotein inhibitior + 0.7527 75.27%
P-glycoprotein substrate + 0.5673 56.73%
CYP3A4 substrate + 0.7387 73.87%
CYP2C9 substrate - 0.8018 80.18%
CYP2D6 substrate - 0.8966 89.66%
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 + 0.7646 76.46%
CYP inhibitory promiscuity - 0.9733 97.33%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6024 60.24%
Eye corrosion - 0.9896 98.96%
Eye irritation - 0.9013 90.13%
Skin irritation - 0.5876 58.76%
Skin corrosion - 0.9441 94.41%
Ames mutagenesis - 0.6548 65.48%
Human Ether-a-go-go-Related Gene inhibition + 0.7026 70.26%
Micronuclear - 0.7800 78.00%
Hepatotoxicity - 0.7194 71.94%
skin sensitisation - 0.9013 90.13%
Respiratory toxicity - 0.5222 52.22%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity - 0.6250 62.50%
Nephrotoxicity + 0.5784 57.84%
Acute Oral Toxicity (c) III 0.8023 80.23%
Estrogen receptor binding + 0.7657 76.57%
Androgen receptor binding + 0.7527 75.27%
Thyroid receptor binding + 0.5902 59.02%
Glucocorticoid receptor binding + 0.7957 79.57%
Aromatase binding + 0.6348 63.48%
PPAR gamma + 0.8218 82.18%
Honey bee toxicity - 0.6989 69.89%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5800 58.00%
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 98.38% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.06% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.01% 96.09%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 91.47% 91.07%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.13% 86.33%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 89.91% 94.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.02% 95.56%
CHEMBL2782 P35610 Acyl coenzyme A:cholesterol acyltransferase 1 88.93% 91.65%
CHEMBL221 P23219 Cyclooxygenase-1 88.18% 90.17%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.78% 95.89%
CHEMBL1937 Q92769 Histone deacetylase 2 85.81% 94.75%
CHEMBL3060 Q9Y345 Glycine transporter 2 84.49% 99.17%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 84.40% 93.00%
CHEMBL5028 O14672 ADAM10 84.22% 97.50%
CHEMBL2563 Q9UQL6 Histone deacetylase 5 83.52% 89.67%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.49% 89.00%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 83.19% 95.50%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 82.92% 95.50%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 81.85% 96.90%
CHEMBL2096618 P11274 Bcr/Abl fusion protein 81.74% 85.83%
CHEMBL4302 P08183 P-glycoprotein 1 81.03% 92.98%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.81% 100.00%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.13% 92.62%

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.
Polyspora chrysandra

Cross-Links

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PubChem 163192165
LOTUS LTS0031060
wikiData Q105304804