Gymnemic acid IX

Details

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Internal ID d01cad3b-f751-408f-9660-8ffd443e9eec
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-[(E)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-[(2S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-oxooxan-2-yl]oxy-3,5-dihydroxyoxane-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(=O)C(C(C(O7)CO)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[C@H]7C(=O)[C@H]([C@@H]([C@H](O7)CO)O)O)O)C)C)[C@@H]2CC1(C)C)C)O)CO)O
InChI InChI=1S/C47H72O18/c1-9-21(2)39(60)65-37-36(57)47(20-50)23(16-42(37,3)4)22-10-11-26-43(5)14-13-28(44(6,19-49)25(43)12-15-45(26,7)46(22,8)17-27(47)51)62-41-33(56)34(32(55)35(64-41)38(58)59)63-40-31(54)30(53)29(52)24(18-48)61-40/h9-10,23-30,32-37,40-41,48-53,55-57H,11-20H2,1-8H3,(H,58,59)/b21-9+/t23-,24+,25+,26+,27-,28-,29+,30-,32-,33+,34-,35-,36-,37-,40-,41+,43-,44-,45+,46+,47-/m0/s1
InChI Key CZFCLAXAWADCPY-RSUBFJOJSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C47H72O18
Molecular Weight 925.10 g/mol
Exact Mass 924.47186544 g/mol
Topological Polar Surface Area (TPSA) 300.00 Ų
XlogP 2.70
Atomic LogP (AlogP) 0.49
H-Bond Acceptor 17
H-Bond Donor 10
Rotatable Bonds 10

Synonyms

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Gymnemic acid ix, (+)-
UNII-4QWR1P5B0N
4QWR1P5B0N
131653-20-8
beta-D-Glucopyranosiduronic acid, (3beta,4alpha,16beta,21beta(E),22alpha)-16,22,23,28-tetrahydroxy-21-((2-methyl-1-oxo-2-butenyl)oxy)olean-12-en-3-yl 3-o-beta-D-arabino-hexopyranos-2-ulos-1-yl-
Q27260377
GYMNEMIC ACID IX (CONSTITUENT OF GYMNEMA) [DSC]
.BETA.-D-GLUCOPYRANOSIDURONIC ACID, (3.BETA.,4.ALPHA.,16.BETA.,21.BETA.(E),22.ALPHA.)-16,22,23,28-TETRAHYDROXY-21-((2-METHYL-1-OXO-2-BUTENYL)OXY)OLEAN-12-EN-3-YL 3-O-.BETA.-D-ARABINO-HEXOPYRANOS-2-ULOS-1-YL-

2D Structure

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2D Structure of Gymnemic acid IX

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 - 0.8747 87.47%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.8703 87.03%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8031 80.31%
OATP1B3 inhibitior - 0.4610 46.10%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.5026 50.26%
BSEP inhibitior + 0.7684 76.84%
P-glycoprotein inhibitior + 0.7528 75.28%
P-glycoprotein substrate + 0.5795 57.95%
CYP3A4 substrate + 0.7400 74.00%
CYP2C9 substrate - 0.8006 80.06%
CYP2D6 substrate - 0.8970 89.70%
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 + 0.7662 76.62%
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 - 0.9033 90.33%
Skin irritation - 0.5876 58.76%
Skin corrosion - 0.9441 94.41%
Ames mutagenesis - 0.7270 72.70%
Human Ether-a-go-go-Related Gene inhibition + 0.7243 72.43%
Micronuclear - 0.7800 78.00%
Hepatotoxicity - 0.7117 71.17%
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 + 0.8376 83.76%
Acute Oral Toxicity (c) III 0.8023 80.23%
Estrogen receptor binding + 0.8029 80.29%
Androgen receptor binding + 0.7579 75.79%
Thyroid receptor binding - 0.4896 48.96%
Glucocorticoid receptor binding + 0.7880 78.80%
Aromatase binding + 0.6126 61.26%
PPAR gamma + 0.8159 81.59%
Honey bee toxicity - 0.6629 66.29%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.6100 61.00%
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 97.36% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 97.27% 94.45%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 93.64% 91.07%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 93.01% 93.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.31% 86.33%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.07% 96.09%
CHEMBL221 P23219 Cyclooxygenase-1 92.05% 90.17%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.46% 95.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 89.68% 95.89%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.40% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.47% 97.09%
CHEMBL2581 P07339 Cathepsin D 85.72% 98.95%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 84.91% 94.33%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.83% 100.00%
CHEMBL5255 O00206 Toll-like receptor 4 81.64% 92.50%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.99% 99.23%
CHEMBL1293267 Q9HC97 G-protein coupled receptor 35 80.66% 89.34%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 80.12% 95.50%

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 91617808
LOTUS LTS0216653
wikiData Q27260377