helonioside A

Details

• Internal ID: 5bd995a1-ac4d-4994-a660-aa635f81b9af
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3R,4S,5S)-3-hydroxy-4-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy-5-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)OCC2C(C(C(O2)(CO)OC3C(C(C(C(O3)CO)O)O)O)OC(=O)C=CC4=CC(=C(C=C4)O)OC)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@](O2)(CO)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)OC(=O)/C=C/C4=CC(=C(C=C4)O)OC)O)O
• InChI: InChI=1S/C32H38O17/c1-43-20-11-16(3-7-18(20)35)5-9-24(37)45-14-23-27(40)30(47-25(38)10-6-17-4-8-19(36)21(12-17)44-2)32(15-34,48-23)49-31-29(42)28(41)26(39)22(13-33)46-31/h3-12,22-23,26-31,33-36,39-42H,13-15H2,1-2H3/b9-5+,10-6+/t22-,23-,26-,27-,28+,29-,30+,31-,32+/m1/s1
• InChI Key: ZPIDHNQIWCJXAS-SOUWYMHNSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₃₈O₁₇
• Molecular Weight: 694.60 g/mol
• Exact Mass: 694.21089974 g/mol
• Topological Polar Surface Area (TPSA): 261.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -1.44
• H-Bond Acceptor: 17
• H-Bond Donor: 8
• Rotatable Bonds: 13

Synonyms

• SCHEMBL9928774
• CHEMBL2151691
• NCGC00380914-01
• NCGC00380914-01_C32H38O17_alpha-D-Glucopyranoside, 3,6-bis-O-[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl]-beta-D-fructofuranosyl

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7932	79.32%
Caco-2	-	0.8952	89.52%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7226	72.26%
OATP2B1 inhibitior	-	0.7234	72.34%
OATP1B1 inhibitior	+	0.8660	86.60%
OATP1B3 inhibitior	+	0.9557	95.57%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8667	86.67%
P-glycoprotein inhibitior	+	0.6592	65.92%
P-glycoprotein substrate	-	0.7177	71.77%
CYP3A4 substrate	+	0.6457	64.57%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8593	85.93%
CYP3A4 inhibition	-	0.7733	77.33%
CYP2C9 inhibition	-	0.8269	82.69%
CYP2C19 inhibition	-	0.7818	78.18%
CYP2D6 inhibition	-	0.9225	92.25%
CYP1A2 inhibition	-	0.8862	88.62%
CYP2C8 inhibition	+	0.7451	74.51%
CYP inhibitory promiscuity	-	0.7325	73.25%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6680	66.80%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9215	92.15%
Skin irritation	-	0.8527	85.27%
Skin corrosion	-	0.9511	95.11%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8206	82.06%
Micronuclear	-	0.5326	53.26%
Hepatotoxicity	-	0.8699	86.99%
skin sensitisation	-	0.8034	80.34%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.8999	89.99%
Acute Oral Toxicity (c)	III	0.6640	66.40%
Estrogen receptor binding	+	0.8166	81.66%
Androgen receptor binding	+	0.6476	64.76%
Thyroid receptor binding	+	0.5321	53.21%
Glucocorticoid receptor binding	+	0.6536	65.36%
Aromatase binding	+	0.5614	56.14%
PPAR gamma	+	0.7101	71.01%
Honey bee toxicity	-	0.7425	74.25%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9363	93.63%

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	99.68%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.80%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.31%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.09%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.98%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.56%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	91.47%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.40%	85.14%
CHEMBL3194	P02766	Transthyretin	90.06%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.20%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	88.20%	91.49%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.78%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.26%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.84%	94.45%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.40%	89.62%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.77%	97.36%
CHEMBL4208	P20618	Proteasome component C5	82.94%	90.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.84%	92.62%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.12%	86.92%

Plants that contains it

• Ageratina adenophora
• Boehmeria nivea
• Crotalaria micans
• Croton poilanei
• Dasymaschalon sootepense
• Dictyoloma vandellianum
• Euonymus sachalinensis
• Felicia erigeroides
• Flueggea virosa subsp. melanthesoides
• Guatteria megalophylla
• Lupinus paniculatus
• Lycoris traubii
• Lygodium flexuosum
• Panax ginseng
• Paris polyphylla
• Saccharum spontaneum
• Smilax bracteata
• Smilax china
• Smilax glabra
• Strychnos staudtii
• Tsuga mertensiana

Cross-Links

• PubChem: 16745274
• NPASS: NPC262182
• LOTUS: LTS0154285
• wikiData: Q105380924