[(2S,3R,4S,5S,6R)-2-[[(1R,15S,16R,17S)-16-ethenyl-4,5-dihydroxy-11-oxo-14-oxa-10-azatetracyclo[8.8.0.02,7.012,17]octadeca-2,4,6,12-tetraen-15-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Details

• Internal ID: 4d0fca94-7ca8-4d2a-b31f-a35dcd0960fe
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2S,3R,4S,5S,6R)-2-[[(1R,15S,16R,17S)-16-ethenyl-4,5-dihydroxy-11-oxo-14-oxa-10-azatetracyclo[8.8.0.02,7.012,17]octadeca-2,4,6,12-tetraen-15-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)OC2C(C(C(OC2OC3C(C4CC5C6=CC(=C(C=C6CCN5C(=O)C4=CO3)O)O)C=C)CO)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2O[C@H]3[C@@H]([C@@H]4C[C@@H]5C6=CC(=C(C=C6CCN5C(=O)C4=CO3)O)O)C=C)CO)O)O)O
• InChI: InChI=1S/C34H37NO13/c1-3-18-20-12-22-19-13-25(39)24(38)11-17(19)8-9-35(22)32(43)21(20)15-45-33(18)48-34-31(30(42)29(41)27(14-36)46-34)47-28(40)7-5-16-4-6-23(37)26(10-16)44-2/h3-7,10-11,13,15,18,20,22,27,29-31,33-34,36-39,41-42H,1,8-9,12,14H2,2H3/b7-5+/t18-,20+,22-,27-,29-,30+,31-,33+,34+/m1/s1
• InChI Key: LEWOWBPQXHWNSQ-ZYRCMWDHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₃₇NO₁₃
• Molecular Weight: 667.70 g/mol
• Exact Mass: 667.22649023 g/mol
• Topological Polar Surface Area (TPSA): 205.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.38
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4745	47.45%
Caco-2	-	0.8849	88.49%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.6163	61.63%
OATP2B1 inhibitior	-	0.5796	57.96%
OATP1B1 inhibitior	+	0.8239	82.39%
OATP1B3 inhibitior	+	0.9342	93.42%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.7761	77.61%
P-glycoprotein inhibitior	+	0.6971	69.71%
P-glycoprotein substrate	+	0.6611	66.11%
CYP3A4 substrate	+	0.7230	72.30%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8574	85.74%
CYP3A4 inhibition	-	0.8530	85.30%
CYP2C9 inhibition	-	0.8066	80.66%
CYP2C19 inhibition	-	0.8098	80.98%
CYP2D6 inhibition	-	0.8500	85.00%
CYP1A2 inhibition	-	0.7324	73.24%
CYP2C8 inhibition	+	0.7512	75.12%
CYP inhibitory promiscuity	-	0.8945	89.45%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5047	50.47%
Eye corrosion	-	0.9855	98.55%
Eye irritation	-	0.9220	92.20%
Skin irritation	-	0.7672	76.72%
Skin corrosion	-	0.9348	93.48%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6505	65.05%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.8591	85.91%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.9513	95.13%
Acute Oral Toxicity (c)	III	0.6227	62.27%
Estrogen receptor binding	+	0.8283	82.83%
Androgen receptor binding	+	0.6854	68.54%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6453	64.53%
Aromatase binding	+	0.5208	52.08%
PPAR gamma	+	0.6895	68.95%
Honey bee toxicity	-	0.6965	69.65%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.8941	89.41%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.54%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.38%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	98.23%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.90%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.85%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.09%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.08%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.97%	86.92%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.75%	85.14%
CHEMBL2581	P07339	Cathepsin D	92.66%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.41%	97.09%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	91.18%	89.62%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	90.13%	80.78%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.01%	95.89%
CHEMBL4208	P20618	Proteasome component C5	87.91%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.33%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.35%	95.89%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	84.10%	98.00%
CHEMBL340	P08684	Cytochrome P450 3A4	83.82%	91.19%
CHEMBL1902	P62942	FK506-binding protein 1A	83.53%	97.05%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.92%	95.83%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	82.61%	90.24%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	82.59%	91.03%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.14%	92.94%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.06%	100.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.59%	90.71%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.56%	96.95%

Plants that contains it

• Helichrysum umbraculigerum

Cross-Links

• PubChem: 101688455
• LOTUS: LTS0118063
• wikiData: Q105283365