Hellicoside

Details

• Internal ID: 4d1ee60c-56ac-42c1-bba7-71a846da7406
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3R,4R,5R,6R)-6-[(2S)-2-(3,4-dihydroxyphenyl)-2-hydroxyethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1=CC(=C(C=C1C=CC(=O)OC2C(OC(C(C2OC3C(C(C(C(O3)CO)O)O)O)O)OCC(C4=CC(=C(C=C4)O)O)O)CO)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1/C=C/C(=O)O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)OC[C@H](C4=CC(=C(C=C4)O)O)O)CO)O)O
• InChI: InChI=1S/C29H36O17/c30-9-19-22(38)23(39)24(40)29(43-19)46-27-25(41)28(42-11-18(36)13-3-5-15(33)17(35)8-13)44-20(10-31)26(27)45-21(37)6-2-12-1-4-14(32)16(34)7-12/h1-8,18-20,22-36,38-41H,9-11H2/b6-2+/t18-,19-,20-,22-,23+,24-,25-,26-,27-,28-,29+/m1/s1
• InChI Key: IKASMYQBXBUEQS-AEAUTZEXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₆O₁₇
• Molecular Weight: 656.60 g/mol
• Exact Mass: 656.19524968 g/mol
• Topological Polar Surface Area (TPSA): 286.00 Ų
• XlogP: -2.10
• Atomic LogP (AlogP): -2.55
• H-Bond Acceptor: 17
• H-Bond Donor: 11
• Rotatable Bonds: 11

Synonyms

• 132278-04-7
• [(2R,3R,4R,5R,6R)-6-[(2S)-2-(3,4-dihydroxyphenyl)-2-hydroxyethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• C10466
• [(2R,3R,4S,5R,6R)-6-[(2S)-2-(3,4-dihydroxyphenyl)-2-hydroxy-ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(
• AC1NQZ2B
• CHEBI:5646
• DTXSID00415190
• Q27106848
• [(2R,3R,4R,5R,6R)-6-[(2S)-2-(3,4-dihydroxyphenyl)-2-hydroxy-ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7183	71.83%
Caco-2	-	0.9139	91.39%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.5244	52.44%
OATP2B1 inhibitior	-	0.8497	84.97%
OATP1B1 inhibitior	+	0.8837	88.37%
OATP1B3 inhibitior	+	0.9503	95.03%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6421	64.21%
P-glycoprotein inhibitior	-	0.5440	54.40%
P-glycoprotein substrate	-	0.7385	73.85%
CYP3A4 substrate	+	0.6024	60.24%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8666	86.66%
CYP3A4 inhibition	-	0.9067	90.67%
CYP2C9 inhibition	-	0.9478	94.78%
CYP2C19 inhibition	-	0.9384	93.84%
CYP2D6 inhibition	-	0.8969	89.69%
CYP1A2 inhibition	-	0.9489	94.89%
CYP2C8 inhibition	+	0.5338	53.38%
CYP inhibitory promiscuity	-	0.8526	85.26%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7067	70.67%
Eye corrosion	-	0.9945	99.45%
Eye irritation	-	0.9067	90.67%
Skin irritation	-	0.8347	83.47%
Skin corrosion	-	0.9633	96.33%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6896	68.96%
Micronuclear	+	0.5033	50.33%
Hepatotoxicity	-	0.8591	85.91%
skin sensitisation	-	0.7946	79.46%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.9601	96.01%
Acute Oral Toxicity (c)	III	0.6587	65.87%
Estrogen receptor binding	+	0.7818	78.18%
Androgen receptor binding	-	0.5621	56.21%
Thyroid receptor binding	+	0.5555	55.55%
Glucocorticoid receptor binding	-	0.5055	50.55%
Aromatase binding	+	0.5490	54.90%
PPAR gamma	+	0.7066	70.66%
Honey bee toxicity	-	0.6170	61.70%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
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	99.85%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.61%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.80%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.99%	89.00%
CHEMBL3194	P02766	Transthyretin	91.82%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.66%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	89.42%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.62%	94.45%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	87.35%	97.53%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.33%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.00%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.86%	86.92%
CHEMBL2581	P07339	Cathepsin D	86.26%	98.95%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	86.02%	94.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.59%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.54%	86.33%
CHEMBL4208	P20618	Proteasome component C5	83.12%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.40%	97.09%

Plants that contains it

• Allium stipitatum
• Alstonia longifolia
• Angiopteris evecta
• Artemisia argentea
• Asphodeline damascena
• Brodiaea californica
• Cyathula tomentosa
• Echinostephia aculeata
• Eucalyptus kitsoniana
• Euphorbia antiquorum
• Exochorda racemosa subsp. giraldii
• Hemionitis lemmonii
• Himantoglossum hircinum
• Kopsia arborea
• Lepidophorum repandum
• Myristica malabarica
• Odontites vernus
• Plagiomnium cuspidatum
• Plantago asiatica
• Plantago depressa
• Plantago major
• Plectranthus lanuginosus
• Populus yunnanensis
• Rhodanthe maryonii
• Rhododendron campylocarpum
• Sagina japonica
• Scabiosa comosa
• Scapania aequiloba
• Solanum dulcamara
• Spartium junceum
• Toddalia asiatica
• Vachellia lasiopetala

Cross-Links

• PubChem: 5281778
• NPASS: NPC282779
• LOTUS: LTS0174069
• wikiData: Q27106848