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

Details

• Internal ID: fea45cba-a0e4-4c0f-b767-16a8e6f917e2
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Glycodepsipeptides
• IUPAC Name: [1-[[(1R,4aR,5S,6R,8aS)-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-4-[[(2R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3,4,4a,5,6,7,8-octahydro-1H-naphthalen-1-yl]oxy]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl] 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
• SMILES (Isomeric): CC(C)C(C(=O)OC(CC1=CC=C(C=C1)O)C(=O)O[C@@H]2CCC([C@@H]3[C@@]2(CC[C@@H]([C@@H]3O)C(=C)C(=O)OC)C)CO[C@H]4C([C@H]([C@@H]([C@@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C36H52O15/c1-17(2)27(39)34(46)49-23(14-19-6-9-21(38)10-7-19)33(45)51-25-11-8-20(16-48-35-31(43)30(42)29(41)24(15-37)50-35)26-28(40)22(12-13-36(25,26)4)18(3)32(44)47-5/h6-7,9-10,17,20,22-31,35,37-43H,3,8,11-16H2,1-2,4-5H3/t20?,22-,23?,24+,25-,26+,27?,28+,29-,30+,31?,35-,36-/m1/s1
• InChI Key: OFOLFEWVRJZAIJ-MHVLLULQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₂O₁₅
• Molecular Weight: 724.80 g/mol
• Exact Mass: 724.33062095 g/mol
• Topological Polar Surface Area (TPSA): 239.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 0.12
• H-Bond Acceptor: 15
• H-Bond Donor: 7
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7793	77.93%
Caco-2	-	0.8822	88.22%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7953	79.53%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8429	84.29%
OATP1B3 inhibitior	-	0.2266	22.66%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.8829	88.29%
P-glycoprotein inhibitior	+	0.6812	68.12%
P-glycoprotein substrate	+	0.6456	64.56%
CYP3A4 substrate	+	0.7220	72.20%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8707	87.07%
CYP3A4 inhibition	-	0.7162	71.62%
CYP2C9 inhibition	-	0.7091	70.91%
CYP2C19 inhibition	-	0.6007	60.07%
CYP2D6 inhibition	-	0.9254	92.54%
CYP1A2 inhibition	-	0.5796	57.96%
CYP2C8 inhibition	+	0.7106	71.06%
CYP inhibitory promiscuity	-	0.9074	90.74%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7142	71.42%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9167	91.67%
Skin irritation	-	0.7303	73.03%
Skin corrosion	-	0.9445	94.45%
Ames mutagenesis	-	0.6908	69.08%
Human Ether-a-go-go-Related Gene inhibition	+	0.7304	73.04%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.6674	66.74%
skin sensitisation	-	0.8691	86.91%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.7868	78.68%
Acute Oral Toxicity (c)	III	0.5949	59.49%
Estrogen receptor binding	+	0.8164	81.64%
Androgen receptor binding	+	0.7318	73.18%
Thyroid receptor binding	-	0.5202	52.02%
Glucocorticoid receptor binding	+	0.6663	66.63%
Aromatase binding	+	0.6386	63.86%
PPAR gamma	+	0.7318	73.18%
Honey bee toxicity	-	0.6766	67.66%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9926	99.26%

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	99.21%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.99%	96.09%
CHEMBL2581	P07339	Cathepsin D	98.63%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	97.33%	83.82%
CHEMBL4072	P07858	Cathepsin B	96.08%	93.67%
CHEMBL268	P43235	Cathepsin K	94.31%	96.85%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.75%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	92.08%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.78%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.01%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.58%	89.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	87.91%	95.83%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.22%	95.56%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	86.94%	85.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.96%	85.14%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.42%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.10%	99.17%
CHEMBL5255	O00206	Toll-like receptor 4	84.45%	92.50%
CHEMBL2514	O95665	Neurotensin receptor 2	84.06%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.00%	97.14%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.46%	94.33%
CHEMBL221	P23219	Cyclooxygenase-1	81.45%	90.17%
CHEMBL340	P08684	Cytochrome P450 3A4	81.27%	91.19%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.15%	92.62%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.03%	100.00%

Plants that contains it

• Ixeris repens

Cross-Links

• PubChem: 101589329
• LOTUS: LTS0238998
• wikiData: Q105191321