NCGC00168892-03_C30H38O17_beta-D-Glucopyranoside, (1aS,1bS,2S,5aR,6S,6aS)-6-[[6-deoxy-3-O-[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]-alpha-L-mannopyranosyl]oxy]-1a,1b,2,5a,6,6a-hexahydro-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl

Details

• Internal ID: 31dc3593-3739-4fda-afc2-9ce27f441451
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2S,3R,4R,5S,6S)-3,5-dihydroxy-2-[[(1S,2S,4S,5S,6R,10S)-2-(hydroxymethyl)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl]oxy]-6-methyloxan-4-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C3C=COC(C3C4(C2O4)CO)OC5C(C(C(C(O5)CO)O)O)O)O)OC(=O)C=CC6=CC(=C(C=C6)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2[C@@H]3C=CO[C@H]([C@@H]3[C@@]4([C@H]2O4)CO)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)OC(=O)/C=C/C6=CC(=C(C=C6)O)O)O
• InChI: InChI=1S/C30H38O17/c1-11-19(36)25(44-17(35)5-3-12-2-4-14(33)15(34)8-12)23(40)29(42-11)45-24-13-6-7-41-27(18(13)30(10-32)26(24)47-30)46-28-22(39)21(38)20(37)16(9-31)43-28/h2-8,11,13,16,18-29,31-34,36-40H,9-10H2,1H3/b5-3+/t11-,13+,16+,18+,19-,20+,21-,22+,23+,24-,25+,26-,27-,28-,29-,30+/m0/s1
• InChI Key: MFIJTASICGGFJA-LAJFDIHTSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₈O₁₇
• Molecular Weight: 670.60 g/mol
• Exact Mass: 670.21089974 g/mol
• Topological Polar Surface Area (TPSA): 267.00 Ų
• XlogP: -2.40
• Atomic LogP (AlogP): -3.06
• H-Bond Acceptor: 17
• H-Bond Donor: 9
• Rotatable Bonds: 9

Synonyms

• ACon1_000634
• ACon1_001816
• NCGC00168892-01
• NCGC00168892-02
• NCGC00168892-03
• NCGC00168892-03_C30H38O17_beta-D-Glucopyranoside, (1aS,1bS,2S,5aR,6S,6aS)-6-[[6-deoxy-3-O-[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]-alpha-L-mannopyranosyl]oxy]-1a,1b,2,5a,6,6a-hexahydro-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6506	65.06%
Caco-2	-	0.8899	88.99%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.6394	63.94%
OATP2B1 inhibitior	-	0.8616	86.16%
OATP1B1 inhibitior	+	0.8318	83.18%
OATP1B3 inhibitior	+	0.9620	96.20%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.5969	59.69%
P-glycoprotein inhibitior	-	0.4661	46.61%
P-glycoprotein substrate	+	0.5071	50.71%
CYP3A4 substrate	+	0.6891	68.91%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8727	87.27%
CYP3A4 inhibition	-	0.9263	92.63%
CYP2C9 inhibition	-	0.8672	86.72%
CYP2C19 inhibition	-	0.7360	73.60%
CYP2D6 inhibition	-	0.8925	89.25%
CYP1A2 inhibition	-	0.8376	83.76%
CYP2C8 inhibition	+	0.6809	68.09%
CYP inhibitory promiscuity	-	0.6825	68.25%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5683	56.83%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9213	92.13%
Skin irritation	-	0.7787	77.87%
Skin corrosion	-	0.9407	94.07%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4155	41.55%
Micronuclear	+	0.5333	53.33%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.7776	77.76%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.8552	85.52%
Acute Oral Toxicity (c)	III	0.5086	50.86%
Estrogen receptor binding	+	0.7247	72.47%
Androgen receptor binding	+	0.5301	53.01%
Thyroid receptor binding	+	0.5140	51.40%
Glucocorticoid receptor binding	+	0.6374	63.74%
Aromatase binding	+	0.5261	52.61%
PPAR gamma	+	0.6853	68.53%
Honey bee toxicity	-	0.7017	70.17%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.8099	80.99%

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	99.90%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.55%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.85%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.08%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.84%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.32%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.98%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	90.47%	94.73%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.70%	97.36%
CHEMBL2581	P07339	Cathepsin D	88.60%	98.95%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	86.43%	80.78%
CHEMBL4208	P20618	Proteasome component C5	86.20%	90.00%
CHEMBL3194	P02766	Transthyretin	85.11%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.10%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.20%	86.92%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.19%	94.45%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.80%	92.94%

Plants that contains it

• Premna odorata
• Verbascum thapsus

Cross-Links

• PubChem: 14263159
• LOTUS: LTS0127916
• wikiData: Q105162701