(2S)-2-[(3S,4R,4aS)-4-ethenyl-8-oxo-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyridin-7-yl]-3-phenylpropanoic acid

Details

• Internal ID: 0a7fdd1c-f411-4a10-935d-56011f785a8d
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Phenylalanine and derivatives
• IUPAC Name: (2S)-2-[(3S,4R,4aS)-4-ethenyl-8-oxo-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyridin-7-yl]-3-phenylpropanoic acid
• SMILES (Canonical): C=CC1C2CCN(C(=O)C2=COC1OC3C(C(C(C(O3)CO)O)O)O)C(CC4=CC=CC=C4)C(=O)O
• SMILES (Isomeric): C=C[C@@H]1[C@@H]2CCN(C(=O)C2=CO[C@H]1O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)[C@@H](CC4=CC=CC=C4)C(=O)O
• InChI: InChI=1S/C25H31NO10/c1-2-14-15-8-9-26(17(23(32)33)10-13-6-4-3-5-7-13)22(31)16(15)12-34-24(14)36-25-21(30)20(29)19(28)18(11-27)35-25/h2-7,12,14-15,17-21,24-25,27-30H,1,8-11H2,(H,32,33)/t14-,15+,17+,18-,19-,20+,21-,24+,25+/m1/s1
• InChI Key: KUYOOBCAZIUXQE-NJKXIOODSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₁NO₁₀
• Molecular Weight: 505.50 g/mol
• Exact Mass: 505.19479619 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): -0.61
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5739	57.39%
Caco-2	-	0.8605	86.05%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6268	62.68%
OATP2B1 inhibitior	-	0.8562	85.62%
OATP1B1 inhibitior	+	0.8649	86.49%
OATP1B3 inhibitior	+	0.9318	93.18%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.4780	47.80%
P-glycoprotein inhibitior	-	0.5211	52.11%
P-glycoprotein substrate	-	0.7038	70.38%
CYP3A4 substrate	+	0.6540	65.40%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8650	86.50%
CYP3A4 inhibition	-	0.8538	85.38%
CYP2C9 inhibition	-	0.8677	86.77%
CYP2C19 inhibition	-	0.8694	86.94%
CYP2D6 inhibition	-	0.9197	91.97%
CYP1A2 inhibition	-	0.7479	74.79%
CYP2C8 inhibition	+	0.4806	48.06%
CYP inhibitory promiscuity	-	0.9128	91.28%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5063	50.63%
Eye corrosion	-	0.9850	98.50%
Eye irritation	-	0.9487	94.87%
Skin irritation	-	0.7630	76.30%
Skin corrosion	-	0.9335	93.35%
Ames mutagenesis	-	0.6070	60.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.3700	37.00%
Micronuclear	+	0.8900	89.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8624	86.24%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.7356	73.56%
Acute Oral Toxicity (c)	III	0.5632	56.32%
Estrogen receptor binding	+	0.7776	77.76%
Androgen receptor binding	+	0.6438	64.38%
Thyroid receptor binding	-	0.5731	57.31%
Glucocorticoid receptor binding	-	0.4865	48.65%
Aromatase binding	-	0.5569	55.69%
PPAR gamma	+	0.6348	63.48%
Honey bee toxicity	-	0.7684	76.84%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.8005	80.05%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.01%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.80%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.39%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.32%	91.11%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	89.35%	93.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.26%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.15%	86.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.34%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.35%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.27%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	83.90%	95.93%
CHEMBL2327	P21452	Neurokinin 2 receptor	83.77%	98.89%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	83.20%	95.17%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.24%	95.83%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.14%	97.14%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.12%	96.61%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.57%	94.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.52%	94.45%

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: 66552683
• NPASS: NPC306443