(1R,4S,7S,9S,10S,13R,15S)-15-hydroxy-7-[(2R,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3-(3-methylbutanoyloxy)-4-sulfooxyoxan-2-yl]oxy-9-methyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5,5-dicarboxylic acid

Details

• Internal ID: ef65d01c-a5c7-4956-9e0c-3db722a847e9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: (1R,4S,7S,9S,10S,13R,15S)-15-hydroxy-7-[(2R,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3-(3-methylbutanoyloxy)-4-sulfooxyoxan-2-yl]oxy-9-methyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5,5-dicarboxylic acid
• SMILES (Canonical): CC(C)CC(=O)OC1C(C(C(OC1OC2CC3(C4CCC5CC4(CCC3C(C2)(C(=O)O)C(=O)O)C(C5=C)O)C)CO)O)OS(=O)(=O)O
• SMILES (Isomeric): CC(C)CC(=O)O[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1O[C@H]2C[C@]3([C@@H]4CC[C@@H]5C[C@@]4(CC[C@@H]3C(C2)(C(=O)O)C(=O)O)[C@H](C5=C)O)C)CO)O)OS(=O)(=O)O
• InChI: InChI=1S/C31H46O15S/c1-14(2)9-21(33)45-24-23(46-47(40,41)42)22(34)18(13-32)44-26(24)43-17-11-29(4)19-6-5-16-10-30(19,25(35)15(16)3)8-7-20(29)31(12-17,27(36)37)28(38)39/h14,16-20,22-26,32,34-35H,3,5-13H2,1-2,4H3,(H,36,37)(H,38,39)(H,40,41,42)/t16-,17+,18-,19+,20+,22-,23+,24-,25+,26-,29+,30-/m1/s1
• InChI Key: YGOAVAYXZNQEGO-LNQSNDDKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₆O₁₅S
• Molecular Weight: 690.80 g/mol
• Exact Mass: 690.25574193 g/mol
• Topological Polar Surface Area (TPSA): 252.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.29
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8801	88.01%
Caco-2	-	0.8558	85.58%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.4870	48.70%
OATP2B1 inhibitior	-	0.7178	71.78%
OATP1B1 inhibitior	+	0.8761	87.61%
OATP1B3 inhibitior	+	0.9347	93.47%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8776	87.76%
BSEP inhibitior	+	0.7120	71.20%
P-glycoprotein inhibitior	+	0.6687	66.87%
P-glycoprotein substrate	+	0.5740	57.40%
CYP3A4 substrate	+	0.7036	70.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8725	87.25%
CYP3A4 inhibition	-	0.8565	85.65%
CYP2C9 inhibition	-	0.7237	72.37%
CYP2C19 inhibition	-	0.7104	71.04%
CYP2D6 inhibition	-	0.8701	87.01%
CYP1A2 inhibition	-	0.7228	72.28%
CYP2C8 inhibition	+	0.6134	61.34%
CYP inhibitory promiscuity	-	0.8184	81.84%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.5900	59.00%
Carcinogenicity (trinary)	Non-required	0.6285	62.85%
Eye corrosion	-	0.9776	97.76%
Eye irritation	-	0.9129	91.29%
Skin irritation	-	0.7593	75.93%
Skin corrosion	-	0.9101	91.01%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8003	80.03%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	+	0.8125	81.25%
skin sensitisation	-	0.8556	85.56%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.6247	62.47%
Acute Oral Toxicity (c)	III	0.5851	58.51%
Estrogen receptor binding	+	0.7502	75.02%
Androgen receptor binding	+	0.7077	70.77%
Thyroid receptor binding	-	0.5475	54.75%
Glucocorticoid receptor binding	+	0.6265	62.65%
Aromatase binding	+	0.6241	62.41%
PPAR gamma	+	0.6303	63.03%
Honey bee toxicity	-	0.7364	73.64%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7105	71.05%
Fish aquatic toxicity	+	0.9967	99.67%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	98.03%	96.38%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.27%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.06%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	94.35%	95.93%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.90%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.31%	98.95%
CHEMBL5255	O00206	Toll-like receptor 4	92.27%	92.50%
CHEMBL237	P41145	Kappa opioid receptor	90.52%	98.10%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	86.96%	82.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.71%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.25%	97.09%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.04%	94.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.62%	96.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	85.54%	96.47%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	85.48%	94.97%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.38%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.18%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.53%	95.56%
CHEMBL5028	O14672	ADAM10	84.11%	97.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.09%	95.89%
CHEMBL1937	Q92769	Histone deacetylase 2	83.17%	94.75%
CHEMBL340	P08684	Cytochrome P450 3A4	83.07%	91.19%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.99%	96.21%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.65%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.49%	97.14%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.95%	100.00%
CHEMBL4588	P22894	Matrix metalloproteinase 8	81.21%	94.66%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.87%	89.00%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	80.59%	92.32%

Plants that contains it

• Xanthium spinosum

Cross-Links

• PubChem: 101693291
• LOTUS: LTS0103382
• wikiData: Q105348183