(1R,4R,5R,7R,9R,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-carboxylic acid

Details

• Internal ID: e99611b5-d1fa-41af-9add-d8459b29808b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: (1R,4R,5R,7R,9R,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-carboxylic acid
• SMILES (Canonical): CC(C)CC(=O)OC1C(C(C(OC1OC2CC(C3CCC45CC(CCC4C3(C2)C)C(=C)C5O)C(=O)O)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@H]([C@H]3CC[C@@]45C[C@@H](CC[C@H]4[C@@]3(C2)C)C(=C)[C@@H]5O)C(=O)O)CO)O)OS(=O)(=O)O
• InChI: InChI=1S/C30H46O13S/c1-14(2)9-22(32)42-25-24(43-44(37,38)39)23(33)20(13-31)41-28(25)40-17-10-18(27(35)36)19-7-8-30-11-16(15(3)26(30)34)5-6-21(30)29(19,4)12-17/h14,16-21,23-26,28,31,33-34H,3,5-13H2,1-2,4H3,(H,35,36)(H,37,38,39)/t16-,17-,18-,19-,20-,21+,23-,24+,25-,26+,28-,29-,30-/m1/s1
• InChI Key: KVVMPQXPWXLMIR-QLKRWLHJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₆O₁₃S
• Molecular Weight: 646.70 g/mol
• Exact Mass: 646.26591269 g/mol
• Topological Polar Surface Area (TPSA): 215.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 1.84
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 9

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	-	0.8535	85.35%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.4870	48.70%
OATP2B1 inhibitior	-	0.5774	57.74%
OATP1B1 inhibitior	+	0.9121	91.21%
OATP1B3 inhibitior	+	0.9347	93.47%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8776	87.76%
BSEP inhibitior	+	0.7276	72.76%
P-glycoprotein inhibitior	+	0.6381	63.81%
P-glycoprotein substrate	+	0.5905	59.05%
CYP3A4 substrate	+	0.7213	72.13%
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	+	0.6674	66.74%
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	-	0.9162	91.62%
Skin irritation	-	0.7593	75.93%
Skin corrosion	-	0.9101	91.01%
Ames mutagenesis	-	0.7528	75.28%
Human Ether-a-go-go-Related Gene inhibition	+	0.8055	80.55%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	+	0.8375	83.75%
skin sensitisation	-	0.8556	85.56%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.7857	78.57%
Acute Oral Toxicity (c)	III	0.5851	58.51%
Estrogen receptor binding	+	0.7263	72.63%
Androgen receptor binding	+	0.7239	72.39%
Thyroid receptor binding	-	0.5901	59.01%
Glucocorticoid receptor binding	+	0.5976	59.76%
Aromatase binding	+	0.6074	60.74%
PPAR gamma	+	0.5968	59.68%
Honey bee toxicity	-	0.6894	68.94%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6855	68.55%
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	98.31%	96.38%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.83%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	97.25%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.60%	94.45%
CHEMBL2581	P07339	Cathepsin D	94.82%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.35%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.57%	91.11%
CHEMBL5255	O00206	Toll-like receptor 4	92.30%	92.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.49%	97.09%
CHEMBL237	P41145	Kappa opioid receptor	89.85%	98.10%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.85%	95.50%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	88.63%	94.97%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.66%	96.00%
CHEMBL4588	P22894	Matrix metalloproteinase 8	87.26%	94.66%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.70%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.36%	94.33%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.29%	100.00%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	84.57%	82.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.48%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	84.18%	91.19%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.97%	86.92%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.92%	97.14%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	83.81%	92.32%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.11%	95.89%
CHEMBL5028	O14672	ADAM10	81.91%	97.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.82%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.66%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	80.79%	91.49%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.42%	96.21%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.06%	100.00%

Plants that contains it

• Xanthium spinosum

Cross-Links

• PubChem: 102469579
• LOTUS: LTS0219696
• wikiData: Q105146748