Gymnemic acid XIII

Details

• Internal ID: f1103d65-305a-46e0-b101-4631f7ad18d6
• 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)-8,9,10-trihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-8a-[[(2S)-2-methylbutanoyl]oxymethyl]-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): CCC(C)C(=O)OCC12C(CC(C(C1O)O)(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
• SMILES (Isomeric): CC[C@H](C)C(=O)OC[C@@]12[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]1CC([C@H]([C@@H]2O)O)(C)C)C)O
• InChI: InChI=1S/C41H66O13/c1-9-20(2)34(51)52-19-41-22(16-36(3,4)31(47)32(41)48)21-10-11-24-37(5)14-13-26(53-35-29(46)27(44)28(45)30(54-35)33(49)50)38(6,18-42)23(37)12-15-39(24,7)40(21,8)17-25(41)43/h10,20,22-32,35,42-48H,9,11-19H2,1-8H3,(H,49,50)/t20-,22-,23+,24+,25-,26-,27-,28-,29+,30-,31-,32-,35+,37-,38-,39+,40+,41-/m0/s1
• InChI Key: DAEICXOPEYOMGC-DDRSIQBQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₆₆O₁₃
• Molecular Weight: 767.00 g/mol
• Exact Mass: 766.45034216 g/mol
• Topological Polar Surface Area (TPSA): 224.00 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 2.54
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

• UNII-7LJ084DV2X
• 7LJ084DV2X
• Gymnemic acid XIII (constituent of gymnema) [DSC]
• 155023-61-3
• beta-D-Glucopyranosiduronic acid, (3beta,4alpha,16beta,21beta,22alpha)-16,21,22,23-tetrahydroxy-28-((2S)-2-methyl-1-oxobutoxy)olean-12-en-3-yl
• Gymnemic acid XIII (constituent of gymnema)
• Q27268523
• .BETA.-D-GLUCOPYRANOSIDURONIC ACID, (3.BETA.,4.ALPHA.,16.BETA.,21.BETA.,22.ALPHA.)-16,21,22,23-TETRAHYDROXY-28-((2S)-2-METHYL-1-OXOBUTOXY)OLEAN-12-EN-3-YL

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8818	88.18%
Caco-2	-	0.8697	86.97%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8572	85.72%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8374	83.74%
OATP1B3 inhibitior	-	0.3083	30.83%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.5779	57.79%
P-glycoprotein inhibitior	+	0.7737	77.37%
P-glycoprotein substrate	-	0.5691	56.91%
CYP3A4 substrate	+	0.7192	71.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8862	88.62%
CYP3A4 inhibition	-	0.5782	57.82%
CYP2C9 inhibition	-	0.8180	81.80%
CYP2C19 inhibition	-	0.8550	85.50%
CYP2D6 inhibition	-	0.9304	93.04%
CYP1A2 inhibition	-	0.8646	86.46%
CYP2C8 inhibition	+	0.7415	74.15%
CYP inhibitory promiscuity	-	0.9365	93.65%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6744	67.44%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9103	91.03%
Skin irritation	-	0.5694	56.94%
Skin corrosion	-	0.9444	94.44%
Ames mutagenesis	-	0.7395	73.95%
Human Ether-a-go-go-Related Gene inhibition	+	0.6612	66.12%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.7853	78.53%
skin sensitisation	-	0.9015	90.15%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.8238	82.38%
Acute Oral Toxicity (c)	III	0.7595	75.95%
Estrogen receptor binding	+	0.7066	70.66%
Androgen receptor binding	+	0.7482	74.82%
Thyroid receptor binding	-	0.5684	56.84%
Glucocorticoid receptor binding	+	0.7257	72.57%
Aromatase binding	+	0.6623	66.23%
PPAR gamma	+	0.7543	75.43%
Honey bee toxicity	-	0.7650	76.50%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9763	97.63%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.18%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.64%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.84%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.55%	91.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.03%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.23%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.80%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	86.65%	90.17%
CHEMBL2581	P07339	Cathepsin D	84.67%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.36%	99.17%
CHEMBL226	P30542	Adenosine A1 receptor	84.35%	95.93%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.15%	91.07%
CHEMBL5028	O14672	ADAM10	83.94%	97.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.26%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.99%	92.62%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.67%	96.77%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.48%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.29%	86.33%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	81.04%	97.47%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.94%	95.71%

Plants that contains it

• Gymnema sylvestre

Cross-Links

• PubChem: 14258863
• LOTUS: LTS0208085
• wikiData: Q27268523