Gymnemic acid IX

Details

• 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

• 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

• 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

ADMET Properties (via admetSAR 2)

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

Proven Targets:

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

• Gymnema sylvestre

Cross-Links

• PubChem: 91617808
• LOTUS: LTS0216653
• wikiData: Q27260377