[(2S)-1-[[(1R,4S,4aS,5S,6S,8aR)-4,5-dihydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-4-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-1,2,3,4a,5,6,7,8-octahydronaphthalen-1-yl]oxy]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl] (2R)-2-hydroxy-3-methylbutanoate

Details

• Internal ID: ebe350e9-e3e4-43d5-a1f1-ae306c7753b7
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Glycodepsipeptides
• IUPAC Name: [(2S)-1-[[(1R,4S,4aS,5S,6S,8aR)-4,5-dihydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-4-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-1,2,3,4a,5,6,7,8-octahydronaphthalen-1-yl]oxy]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl] (2R)-2-hydroxy-3-methylbutanoate
• SMILES (Canonical): CC(C)C(C(=O)OC(CC1=CC=C(C=C1)O)C(=O)OC2CCC(C3C2(CCC(C3O)C(=C)C(=O)OC)C)(COC4C(C(C(C(O4)CO)O)O)O)O)O
• SMILES (Isomeric): CC(C)[C@H](C(=O)O[C@@H](CC1=CC=C(C=C1)O)C(=O)O[C@@H]2CC[C@]([C@H]3[C@]2(CC[C@H]([C@@H]3O)C(=C)C(=O)OC)C)(CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O
• InChI: InChI=1S/C36H52O16/c1-17(2)25(39)33(46)50-22(14-19-6-8-20(38)9-7-19)32(45)52-24-11-13-36(47,16-49-34-29(43)28(42)27(41)23(15-37)51-34)30-26(40)21(10-12-35(24,30)4)18(3)31(44)48-5/h6-9,17,21-30,34,37-43,47H,3,10-16H2,1-2,4-5H3/t21-,22-,23+,24+,25+,26-,27+,28-,29+,30+,34+,35-,36+/m0/s1
• InChI Key: IXOSXWZLCNJRLS-IIMSYPPSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₂O₁₆
• Molecular Weight: 740.80 g/mol
• Exact Mass: 740.32553557 g/mol
• Topological Polar Surface Area (TPSA): 259.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): -0.76
• H-Bond Acceptor: 16
• H-Bond Donor: 8
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8241	82.41%
Caco-2	-	0.8794	87.94%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7600	76.00%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8405	84.05%
OATP1B3 inhibitior	+	0.8166	81.66%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.9275	92.75%
P-glycoprotein inhibitior	+	0.6999	69.99%
P-glycoprotein substrate	+	0.6016	60.16%
CYP3A4 substrate	+	0.7302	73.02%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8761	87.61%
CYP3A4 inhibition	-	0.5835	58.35%
CYP2C9 inhibition	-	0.7100	71.00%
CYP2C19 inhibition	-	0.6216	62.16%
CYP2D6 inhibition	-	0.9229	92.29%
CYP1A2 inhibition	-	0.6027	60.27%
CYP2C8 inhibition	+	0.7660	76.60%
CYP inhibitory promiscuity	-	0.9454	94.54%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7135	71.35%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9134	91.34%
Skin irritation	-	0.7048	70.48%
Skin corrosion	-	0.9431	94.31%
Ames mutagenesis	-	0.7324	73.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.7389	73.89%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.7174	71.74%
skin sensitisation	-	0.8607	86.07%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.8174	81.74%
Acute Oral Toxicity (c)	III	0.5627	56.27%
Estrogen receptor binding	+	0.8170	81.70%
Androgen receptor binding	+	0.7345	73.45%
Thyroid receptor binding	-	0.5117	51.17%
Glucocorticoid receptor binding	+	0.6789	67.89%
Aromatase binding	+	0.6355	63.55%
PPAR gamma	+	0.7434	74.34%
Honey bee toxicity	-	0.6707	67.07%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9888	98.88%

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	99.09%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.11%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	97.82%	83.82%
CHEMBL2581	P07339	Cathepsin D	97.60%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.60%	94.45%
CHEMBL4072	P07858	Cathepsin B	92.53%	93.67%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.77%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.99%	95.89%
CHEMBL268	P43235	Cathepsin K	89.47%	96.85%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.61%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.21%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.13%	97.09%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	87.67%	95.83%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.31%	89.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.16%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.03%	97.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.13%	92.62%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.33%	91.24%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.23%	100.00%
CHEMBL2514	O95665	Neurotensin receptor 2	82.22%	100.00%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	82.19%	82.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.16%	96.00%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	81.14%	85.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.47%	94.33%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	80.03%	94.97%

Plants that contains it

• Ixeris repens

Cross-Links

• PubChem: 162847518
• LOTUS: LTS0247161
• wikiData: Q105122351