methyl (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-phenylpropanoate

Details

• Internal ID: 8f892979-1ea2-4ef7-bae6-7f806f397750
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Phenylalanine and derivatives
• IUPAC Name: methyl (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-phenylpropanoate
• SMILES (Canonical): COC(=O)C(CC1=CC=CC=C1)N2CCC3C(C(OC=C3C2=O)OC4C(C(C(C(O4)CO)O)O)O)C=C
• SMILES (Isomeric): COC(=O)[C@H](CC1=CC=CC=C1)N2CC[C@H]3[C@H]([C@@H](OC=C3C2=O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C=C
• InChI: InChI=1S/C26H33NO10/c1-3-15-16-9-10-27(18(24(33)34-2)11-14-7-5-4-6-8-14)23(32)17(16)13-35-25(15)37-26-22(31)21(30)20(29)19(12-28)36-26/h3-8,13,15-16,18-22,25-26,28-31H,1,9-12H2,2H3/t15-,16+,18+,19-,20-,21+,22-,25+,26+/m1/s1
• InChI Key: YPGCOIVTFNMDTA-DBXUSRIBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₃NO₁₀
• Molecular Weight: 519.50 g/mol
• Exact Mass: 519.21044625 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): -0.52
• H-Bond Acceptor: 10
• H-Bond Donor: 4
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7027	70.27%
Caco-2	-	0.8294	82.94%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6590	65.90%
OATP2B1 inhibitior	-	0.8611	86.11%
OATP1B1 inhibitior	+	0.8507	85.07%
OATP1B3 inhibitior	+	0.9323	93.23%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6030	60.30%
P-glycoprotein inhibitior	+	0.5744	57.44%
P-glycoprotein substrate	-	0.5634	56.34%
CYP3A4 substrate	+	0.6913	69.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8627	86.27%
CYP3A4 inhibition	-	0.8418	84.18%
CYP2C9 inhibition	-	0.8107	81.07%
CYP2C19 inhibition	-	0.8222	82.22%
CYP2D6 inhibition	-	0.9041	90.41%
CYP1A2 inhibition	-	0.7934	79.34%
CYP2C8 inhibition	+	0.5086	50.86%
CYP inhibitory promiscuity	-	0.9021	90.21%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.4647	46.47%
Eye corrosion	-	0.9854	98.54%
Eye irritation	-	0.9540	95.40%
Skin irritation	-	0.7646	76.46%
Skin corrosion	-	0.9304	93.04%
Ames mutagenesis	-	0.6470	64.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.8052	80.52%
Micronuclear	+	0.8100	81.00%
Hepatotoxicity	-	0.6196	61.96%
skin sensitisation	-	0.8618	86.18%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.6035	60.35%
Acute Oral Toxicity (c)	III	0.5797	57.97%
Estrogen receptor binding	+	0.8347	83.47%
Androgen receptor binding	+	0.6770	67.70%
Thyroid receptor binding	-	0.5502	55.02%
Glucocorticoid receptor binding	+	0.6350	63.50%
Aromatase binding	-	0.5606	56.06%
PPAR gamma	+	0.6060	60.60%
Honey bee toxicity	-	0.7811	78.11%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.7170	71.70%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.10%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.73%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.71%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	91.98%	90.17%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	90.22%	93.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.44%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	87.92%	95.83%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.28%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.20%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.40%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.73%	97.14%
CHEMBL218	P21554	Cannabinoid CB1 receptor	85.19%	96.61%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.11%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.12%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.44%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.28%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.11%	97.09%

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: 66552684
• NPASS: NPC195863