(2S,3R,4S)-4-[(E)-2-[5-carboxy-1-[(1S)-1-carboxy-3-methylbutyl]pyridin-1-ium-3-yl]ethenyl]-3-ethenyl-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: dc2e45f4-eb87-4408-a841-791e818ca197
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (2S,3R,4S)-4-[(E)-2-[5-carboxy-1-[(1S)-1-carboxy-3-methylbutyl]pyridin-1-ium-3-yl]ethenyl]-3-ethenyl-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): CC(C)CC(C(=O)O)[N+]1=CC(=CC(=C1)C(=O)O)C=CC2C(C(OC=C2C(=O)[O-])OC3C(C(C(C(O3)CO)O)O)O)C=C
• SMILES (Isomeric): CC(C)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)[O-])O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C=C
• InChI: InChI=1S/C28H35NO13/c1-4-16-17(6-5-14-8-15(24(34)35)10-29(9-14)19(26(38)39)7-13(2)3)18(25(36)37)12-40-27(16)42-28-23(33)22(32)21(31)20(11-30)41-28/h4-6,8-10,12-13,16-17,19-23,27-28,30-33H,1,7,11H2,2-3H3,(H2-,34,35,36,37,38,39)/b6-5+/t16-,17+,19+,20-,21-,22+,23-,27+,28+/m1/s1
• InChI Key: NRCYLHJBIBALDE-TUXMONONSA-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): 227.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): -1.42
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9111	91.11%
Caco-2	-	0.8999	89.99%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.3949	39.49%
OATP2B1 inhibitior	-	0.8543	85.43%
OATP1B1 inhibitior	+	0.7699	76.99%
OATP1B3 inhibitior	+	0.9343	93.43%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5617	56.17%
P-glycoprotein inhibitior	-	0.4701	47.01%
P-glycoprotein substrate	-	0.5298	52.98%
CYP3A4 substrate	+	0.6473	64.73%
CYP2C9 substrate	-	0.7983	79.83%
CYP2D6 substrate	-	0.8726	87.26%
CYP3A4 inhibition	-	0.9455	94.55%
CYP2C9 inhibition	-	0.8022	80.22%
CYP2C19 inhibition	-	0.7637	76.37%
CYP2D6 inhibition	-	0.8764	87.64%
CYP1A2 inhibition	-	0.7815	78.15%
CYP2C8 inhibition	+	0.6360	63.60%
CYP inhibitory promiscuity	-	0.9022	90.22%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.5128	51.28%
Eye corrosion	-	0.9852	98.52%
Eye irritation	-	0.9263	92.63%
Skin irritation	-	0.7834	78.34%
Skin corrosion	-	0.9329	93.29%
Ames mutagenesis	+	0.5277	52.77%
Human Ether-a-go-go-Related Gene inhibition	-	0.4373	43.73%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	-	0.6520	65.20%
skin sensitisation	-	0.8492	84.92%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.4555	45.55%
Acute Oral Toxicity (c)	III	0.6305	63.05%
Estrogen receptor binding	+	0.7304	73.04%
Androgen receptor binding	+	0.6468	64.68%
Thyroid receptor binding	+	0.5517	55.17%
Glucocorticoid receptor binding	+	0.6107	61.07%
Aromatase binding	+	0.6002	60.02%
PPAR gamma	+	0.6506	65.06%
Honey bee toxicity	-	0.6819	68.19%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.8065	80.65%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	97.01%	83.57%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.38%	96.00%
CHEMBL220	P22303	Acetylcholinesterase	96.18%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.86%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.33%	86.33%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	92.50%	89.34%
CHEMBL2581	P07339	Cathepsin D	91.45%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.19%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	90.61%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.14%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.82%	89.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.77%	93.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.63%	90.71%
CHEMBL1811	P34995	Prostanoid EP1 receptor	84.82%	95.71%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.55%	91.11%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.28%	86.92%
CHEMBL226	P30542	Adenosine A1 receptor	84.11%	95.93%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.40%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.58%	96.21%

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: 76309957
• NPASS: NPC12944
• ChEMBL: CHEMBL3092667