(2S)-2-[3-carboxy-5-[(E)-2-[(2S,3R,4S)-3-ethenyl-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]ethenyl]pyridin-1-ium-1-yl]-3-methylbutanoate

Details

• Internal ID: 4041fe40-bece-4958-bd65-4c5e4457eb9d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (2S)-2-[3-carboxy-5-[(E)-2-[(2S,3R,4S)-3-ethenyl-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]ethenyl]pyridin-1-ium-1-yl]-3-methylbutanoate
• SMILES (Canonical): CC(C)C(C(=O)[O-])[N+]1=CC(=CC(=C1)C(=O)O)C=CC2C(C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)C=C
• SMILES (Isomeric): CC(C)[C@@H](C(=O)[O-])[N+]1=CC(=CC(=C1)C(=O)O)/C=C/[C@H]2[C@H]([C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C=C
• InChI: InChI=1S/C28H35NO13/c1-5-16-17(7-6-14-8-15(24(34)35)10-29(9-14)20(13(2)3)25(36)37)18(26(38)39-4)12-40-27(16)42-28-23(33)22(32)21(31)19(11-30)41-28/h5-10,12-13,16-17,19-23,27-28,30-33H,1,11H2,2-4H3,(H-,34,35,36,37)/b7-6+/t16-,17+,19-,20+,21-,22+,23-,27+,28+/m1/s1
• InChI Key: RMIHJDLBWBOJQK-MALFRZCUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₅NO₁₃
• Molecular Weight: 593.60 g/mol
• Exact Mass: 593.21084017 g/mol
• Topological Polar Surface Area (TPSA): 216.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): -1.72
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9624	96.24%
Caco-2	-	0.8846	88.46%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.3597	35.97%
OATP2B1 inhibitior	-	0.5758	57.58%
OATP1B1 inhibitior	+	0.7809	78.09%
OATP1B3 inhibitior	+	0.9340	93.40%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6994	69.94%
P-glycoprotein inhibitior	-	0.4547	45.47%
P-glycoprotein substrate	-	0.5121	51.21%
CYP3A4 substrate	+	0.6535	65.35%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8750	87.50%
CYP3A4 inhibition	-	0.9157	91.57%
CYP2C9 inhibition	-	0.8204	82.04%
CYP2C19 inhibition	-	0.7682	76.82%
CYP2D6 inhibition	-	0.8632	86.32%
CYP1A2 inhibition	-	0.7683	76.83%
CYP2C8 inhibition	+	0.6682	66.82%
CYP inhibitory promiscuity	-	0.9201	92.01%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.4804	48.04%
Eye corrosion	-	0.9850	98.50%
Eye irritation	-	0.9140	91.40%
Skin irritation	-	0.7905	79.05%
Skin corrosion	-	0.9363	93.63%
Ames mutagenesis	+	0.5477	54.77%
Human Ether-a-go-go-Related Gene inhibition	-	0.4316	43.16%
Micronuclear	+	0.8100	81.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8517	85.17%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.5139	51.39%
Acute Oral Toxicity (c)	III	0.6331	63.31%
Estrogen receptor binding	+	0.6935	69.35%
Androgen receptor binding	+	0.5985	59.85%
Thyroid receptor binding	+	0.5688	56.88%
Glucocorticoid receptor binding	+	0.5987	59.87%
Aromatase binding	+	0.5190	51.90%
PPAR gamma	+	0.6200	62.00%
Honey bee toxicity	-	0.7172	71.72%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	-	0.3857	38.57%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.38%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.74%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.24%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	91.58%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.34%	99.17%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	90.08%	89.34%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.99%	91.11%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.57%	90.71%
CHEMBL2581	P07339	Cathepsin D	85.24%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.23%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	84.14%	83.82%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	83.97%	87.67%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.40%	95.89%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	82.65%	92.29%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.60%	96.90%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.56%	89.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.29%	93.56%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.10%	96.21%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.56%	86.92%

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: 76328128
• NPASS: NPC156044