methyl (2S,3R,4S)-3-ethenyl-4-[(E)-4-oxo-4-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(2-methoxy-4-prop-2-enylphenoxy)oxan-2-yl]methoxy]but-1-enyl]-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate

Details

• Internal ID: a2ce2b15-7e92-4c8f-b669-e00fc69abf02
• Taxonomy: Lipids and lipid-like molecules > Saccharolipids
• IUPAC Name: methyl (2S,3R,4S)-3-ethenyl-4-[(E)-4-oxo-4-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(2-methoxy-4-prop-2-enylphenoxy)oxan-2-yl]methoxy]but-1-enyl]-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
• SMILES (Canonical): COC1=C(C=CC(=C1)CC=C)OC2C(C(C(C(O2)COC(=O)CC=CC3C(C(OC=C3C(=O)OC)OC4C(C(C(C(O4)CO)O)O)O)C=C)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)CC=C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)COC(=O)C/C=C/[C@H]3[C@H]([C@@H](OC=C3C(=O)OC)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C=C)O)O)O
• InChI: InChI=1S/C35H46O17/c1-5-8-17-11-12-21(22(13-17)45-3)49-34-30(42)29(41)27(39)24(51-34)16-47-25(37)10-7-9-19-18(6-2)33(48-15-20(19)32(44)46-4)52-35-31(43)28(40)26(38)23(14-36)50-35/h5-7,9,11-13,15,18-19,23-24,26-31,33-36,38-43H,1-2,8,10,14,16H2,3-4H3/b9-7+/t18-,19+,23-,24-,26-,27-,28+,29+,30-,31-,33+,34-,35+/m1/s1
• InChI Key: IHCBIPUOCBZYSU-DWKUXHCQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₆O₁₇
• Molecular Weight: 738.70 g/mol
• Exact Mass: 738.27349999 g/mol
• Topological Polar Surface Area (TPSA): 250.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): -1.25
• H-Bond Acceptor: 17
• H-Bond Donor: 7
• Rotatable Bonds: 15

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6915	69.15%
Caco-2	-	0.8726	87.26%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6499	64.99%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7639	76.39%
OATP1B3 inhibitior	+	0.9599	95.99%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8107	81.07%
P-glycoprotein inhibitior	+	0.7009	70.09%
P-glycoprotein substrate	+	0.5731	57.31%
CYP3A4 substrate	+	0.6990	69.90%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8613	86.13%
CYP3A4 inhibition	-	0.6722	67.22%
CYP2C9 inhibition	-	0.8260	82.60%
CYP2C19 inhibition	-	0.7001	70.01%
CYP2D6 inhibition	-	0.9049	90.49%
CYP1A2 inhibition	-	0.8833	88.33%
CYP2C8 inhibition	+	0.8368	83.68%
CYP inhibitory promiscuity	-	0.7973	79.73%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7245	72.45%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.9160	91.60%
Skin irritation	-	0.8201	82.01%
Skin corrosion	-	0.9431	94.31%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7898	78.98%
Micronuclear	-	0.5541	55.41%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.7723	77.23%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.6911	69.11%
Acute Oral Toxicity (c)	III	0.6248	62.48%
Estrogen receptor binding	+	0.8103	81.03%
Androgen receptor binding	+	0.5350	53.50%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6574	65.74%
Aromatase binding	+	0.5287	52.87%
PPAR gamma	+	0.7408	74.08%
Honey bee toxicity	-	0.6959	69.59%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9526	95.26%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.55%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.83%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.74%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.71%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.49%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	87.63%	94.73%
CHEMBL3286	P00749	Urokinase-type plasminogen activator	87.55%	97.88%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.24%	95.89%
CHEMBL220	P22303	Acetylcholinesterase	86.33%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.25%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.14%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.24%	89.00%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	84.00%	92.29%
CHEMBL1951	P21397	Monoamine oxidase A	83.96%	91.49%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.11%	96.90%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.07%	95.50%
CHEMBL2581	P07339	Cathepsin D	82.94%	98.95%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.60%	97.33%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.18%	96.95%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.02%	90.71%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.61%	92.62%
CHEMBL4208	P20618	Proteasome component C5	80.31%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.00%	94.00%

Plants that contains it

• Acacia aulacocarpa
• Anemonastrum flaccidum
• Ardisia neriifolia
• Aspidosperma subincanum
• Cryptocarya aschersoniana
• Eupatorium argentinum
• Garcinia madruno
• Guatteria ucayalina
• Juniperus brevifolia
• Lonicera japonica
• Peritassa compta
• Psiadia dentata

Cross-Links

• PubChem: 101792585
• NPASS: NPC71852