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(2S,3S,4S,5R,6R)-6-[[(3S,4R,4aR,6aR,6bS,8S,8aR,9R,10R,12aS,14aR,14bR)-8,9-dihydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(Z)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-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 558a185a-9892-4d36-9f43-a6f5d8e40f29
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,8S,8aR,9R,10R,12aS,14aR,14bR)-8,9-dihydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(Z)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-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)O)O)C)CO)O
SMILES (Isomeric) C/C=C(/C)\C(=O)O[C@H]1[C@@H]([C@@]2([C@H](C[C@@]3(C(=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)O)C)C)[C@@H]2CC1(C)C)C)O)CO)O
InChI InChI=1S/C41H64O13/c1-9-20(2)34(51)54-32-31(48)41(19-43)22(16-36(32,3)4)21-10-11-24-37(5)14-13-26(52-35-29(47)27(45)28(46)30(53-35)33(49)50)38(6,18-42)23(37)12-15-39(24,7)40(21,8)17-25(41)44/h9-10,22-32,35,42-48H,11-19H2,1-8H3,(H,49,50)/b20-9-/t22-,23+,24+,25-,26-,27-,28-,29+,30-,31-,32-,35+,37-,38-,39+,40+,41-/m0/s1
InChI Key UOZWTEQSPIEUHT-DJSCHDIESA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C41H64O13
Molecular Weight 764.90 g/mol
Exact Mass 764.43469209 g/mol
Topological Polar Surface Area (TPSA) 224.00 Ų
XlogP 3.80
Atomic LogP (AlogP) 2.46
H-Bond Acceptor 12
H-Bond Donor 8
Rotatable Bonds 7

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,8S,8aR,9R,10R,12aS,14aR,14bR)-8,9-dihydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(Z)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-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 + 0.8010 80.10%
Caco-2 - 0.8722 87.22%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.6857 68.57%
Subcellular localzation Mitochondria 0.8748 87.48%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8328 83.28%
OATP1B3 inhibitior - 0.3922 39.22%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.5276 52.76%
BSEP inhibitior - 0.4634 46.34%
P-glycoprotein inhibitior + 0.7727 77.27%
P-glycoprotein substrate - 0.5775 57.75%
CYP3A4 substrate + 0.7239 72.39%
CYP2C9 substrate - 0.8018 80.18%
CYP2D6 substrate - 0.8966 89.66%
CYP3A4 inhibition - 0.7914 79.14%
CYP2C9 inhibition - 0.8443 84.43%
CYP2C19 inhibition - 0.8871 88.71%
CYP2D6 inhibition - 0.9429 94.29%
CYP1A2 inhibition - 0.8403 84.03%
CYP2C8 inhibition + 0.7673 76.73%
CYP inhibitory promiscuity - 0.9631 96.31%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6861 68.61%
Eye corrosion - 0.9899 98.99%
Eye irritation - 0.9120 91.20%
Skin irritation - 0.6003 60.03%
Skin corrosion - 0.9461 94.61%
Ames mutagenesis - 0.7848 78.48%
Human Ether-a-go-go-Related Gene inhibition + 0.7365 73.65%
Micronuclear - 0.7700 77.00%
Hepatotoxicity - 0.8069 80.69%
skin sensitisation - 0.8982 89.82%
Respiratory toxicity - 0.5667 56.67%
Reproductive toxicity + 0.9222 92.22%
Mitochondrial toxicity - 0.5000 50.00%
Nephrotoxicity + 0.6967 69.67%
Acute Oral Toxicity (c) III 0.8021 80.21%
Estrogen receptor binding + 0.7118 71.18%
Androgen receptor binding + 0.7412 74.12%
Thyroid receptor binding - 0.5623 56.23%
Glucocorticoid receptor binding + 0.7387 73.87%
Aromatase binding + 0.6759 67.59%
PPAR gamma + 0.7605 76.05%
Honey bee toxicity - 0.7149 71.49%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5700 57.00%
Fish aquatic toxicity + 0.9649 96.49%

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 95.32% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.17% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.11% 96.09%
CHEMBL5608 Q16288 NT-3 growth factor receptor 91.24% 95.89%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.23% 95.56%
CHEMBL221 P23219 Cyclooxygenase-1 89.93% 90.17%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 89.12% 91.07%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 88.77% 93.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.09% 86.33%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.47% 89.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.00% 100.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 83.78% 97.09%
CHEMBL3714130 P46095 G-protein coupled receptor 6 83.27% 97.36%
CHEMBL3060 Q9Y345 Glycine transporter 2 82.69% 99.17%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 82.38% 94.33%
CHEMBL4227 P25090 Lipoxin A4 receptor 82.33% 100.00%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 82.07% 95.50%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 81.30% 92.62%
CHEMBL5028 O14672 ADAM10 80.90% 97.50%

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.
Gymnema sylvestre

Cross-Links

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PubChem 162937755
LOTUS LTS0240605
wikiData Q105276661