(2S)-2-[3-[(E)-2-[(2S,3R,4S)-5-carboxy-3-ethenyl-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]propanoate

Details

• Internal ID: 23092526-8ac8-4342-a14b-85da5d9b70ec
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (2S)-2-[3-[(E)-2-[(2S,3R,4S)-5-carboxy-3-ethenyl-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]propanoate
• SMILES (Canonical): CC(C(=O)[O-])[N+]1=CC=CC(=C1)C=CC2C(C(OC=C2C(=O)O)OC3C(C(C(C(O3)CO)O)O)O)C=C
• SMILES (Isomeric): C[C@@H](C(=O)[O-])[N+]1=CC=CC(=C1)/C=C/[C@H]2[C@H]([C@@H](OC=C2C(=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C=C
• InChI: InChI=1S/C24H29NO11/c1-3-14-15(7-6-13-5-4-8-25(9-13)12(2)21(30)31)16(22(32)33)11-34-23(14)36-24-20(29)19(28)18(27)17(10-26)35-24/h3-9,11-12,14-15,17-20,23-24,26-29H,1,10H2,2H3,(H-,30,31,32,33)/b7-6+/t12-,14+,15-,17+,18+,19-,20+,23-,24-/m0/s1
• InChI Key: NAPHCTLCUKYBIG-KMRSAXKXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₉NO₁₁
• Molecular Weight: 507.50 g/mol
• Exact Mass: 507.17406074 g/mol
• Topological Polar Surface Area (TPSA): 190.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): -2.14
• H-Bond Acceptor: 10
• 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	-	0.9507	95.07%
Caco-2	-	0.8874	88.74%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Nucleus	0.3996	39.96%
OATP2B1 inhibitior	-	0.7041	70.41%
OATP1B1 inhibitior	+	0.7672	76.72%
OATP1B3 inhibitior	+	0.9426	94.26%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6535	65.35%
P-glycoprotein inhibitior	-	0.6093	60.93%
P-glycoprotein substrate	-	0.6036	60.36%
CYP3A4 substrate	+	0.6457	64.57%
CYP2C9 substrate	-	0.5961	59.61%
CYP2D6 substrate	-	0.8744	87.44%
CYP3A4 inhibition	-	0.9557	95.57%
CYP2C9 inhibition	-	0.7762	77.62%
CYP2C19 inhibition	-	0.7676	76.76%
CYP2D6 inhibition	-	0.8703	87.03%
CYP1A2 inhibition	-	0.7521	75.21%
CYP2C8 inhibition	+	0.5850	58.50%
CYP inhibitory promiscuity	-	0.8570	85.70%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5500	55.00%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.9402	94.02%
Skin irritation	-	0.7850	78.50%
Skin corrosion	-	0.9354	93.54%
Ames mutagenesis	+	0.5277	52.77%
Human Ether-a-go-go-Related Gene inhibition	-	0.4077	40.77%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	-	0.6822	68.22%
skin sensitisation	-	0.8558	85.58%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.6170	61.70%
Acute Oral Toxicity (c)	III	0.5964	59.64%
Estrogen receptor binding	+	0.5816	58.16%
Androgen receptor binding	+	0.6192	61.92%
Thyroid receptor binding	+	0.6445	64.45%
Glucocorticoid receptor binding	+	0.5530	55.30%
Aromatase binding	+	0.6079	60.79%
PPAR gamma	+	0.6219	62.19%
Honey bee toxicity	-	0.7474	74.74%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	-	0.3803	38.03%

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	97.12%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.42%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.14%	95.56%
CHEMBL2581	P07339	Cathepsin D	92.92%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	91.38%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.23%	86.33%
CHEMBL220	P22303	Acetylcholinesterase	91.13%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.00%	89.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.75%	91.11%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.30%	93.56%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	84.60%	94.08%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	83.95%	83.57%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.63%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.58%	99.17%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.08%	100.00%

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: 76335387
• NPASS: NPC182814
• ChEMBL: CHEMBL3092662