beta-Hydroxyacteoside

Details

• Internal ID: d64ee872-3369-40a4-ad92-9757b6d984c9
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)-2-hydroxyethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C=CC3=CC(=C(C=C3)O)O)CO)OCC(C4=CC(=C(C=C4)O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H](O[C@@H]([C@H]2OC(=O)/C=C/C3=CC(=C(C=C3)O)O)CO)OCC(C4=CC(=C(C=C4)O)O)O)O)O)O)O
• InChI: InChI=1S/C29H36O16/c1-12-22(37)23(38)24(39)29(42-12)45-27-25(40)28(41-11-19(35)14-4-6-16(32)18(34)9-14)43-20(10-30)26(27)44-21(36)7-3-13-2-5-15(31)17(33)8-13/h2-9,12,19-20,22-35,37-40H,10-11H2,1H3/b7-3+/t12-,19?,20+,22-,23+,24+,25+,26+,27+,28+,29-/m0/s1
• InChI Key: XDAXWJHQKZRSEY-XHJPSFMXSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₆O₁₆
• Molecular Weight: 640.60 g/mol
• Exact Mass: 640.20033506 g/mol
• Topological Polar Surface Area (TPSA): 266.00 Ų
• XlogP: -1.60
• Atomic LogP (AlogP): -1.53
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 10

Synonyms

• Campneoside II
• 95587-86-3
• [(2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)-2-hydroxyethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• beta-hydroxy-acteoside
• MEGxp0_000874
• CHEBI:81161
• DTXSID20434020
• HY-N10400
• NSC729647
• NSC-729647
• CS-0527357
• C17528
• E88698
• Q27155116
• 2-(3,4-Dihydroxyphenyl)-2-hydroxyethyl 3-O-(6-deoxy-alpha-L-mannopyranosyl)-4-O-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6804	68.04%
Caco-2	-	0.9036	90.36%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.6457	64.57%
OATP2B1 inhibitior	-	0.8536	85.36%
OATP1B1 inhibitior	+	0.8818	88.18%
OATP1B3 inhibitior	+	0.9549	95.49%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7099	70.99%
P-glycoprotein inhibitior	-	0.5696	56.96%
P-glycoprotein substrate	-	0.5947	59.47%
CYP3A4 substrate	+	0.6266	62.66%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8741	87.41%
CYP3A4 inhibition	-	0.8681	86.81%
CYP2C9 inhibition	-	0.9244	92.44%
CYP2C19 inhibition	-	0.9346	93.46%
CYP2D6 inhibition	-	0.8935	89.35%
CYP1A2 inhibition	-	0.9249	92.49%
CYP2C8 inhibition	+	0.5413	54.13%
CYP inhibitory promiscuity	-	0.7118	71.18%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6969	69.69%
Eye corrosion	-	0.9936	99.36%
Eye irritation	-	0.9152	91.52%
Skin irritation	-	0.8368	83.68%
Skin corrosion	-	0.9536	95.36%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6704	67.04%
Micronuclear	+	0.5133	51.33%
Hepatotoxicity	-	0.8198	81.98%
skin sensitisation	-	0.8020	80.20%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.9708	97.08%
Acute Oral Toxicity (c)	III	0.8048	80.48%
Estrogen receptor binding	+	0.7754	77.54%
Androgen receptor binding	-	0.6340	63.40%
Thyroid receptor binding	+	0.5978	59.78%
Glucocorticoid receptor binding	+	0.5774	57.74%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7049	70.49%
Honey bee toxicity	-	0.6514	65.14%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.7988	79.88%

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%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.69%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.11%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.02%	96.00%
CHEMBL1951	P21397	Monoamine oxidase A	94.82%	91.49%
CHEMBL2581	P07339	Cathepsin D	92.61%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.58%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	92.31%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.94%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.86%	85.14%
CHEMBL3194	P02766	Transthyretin	88.26%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.16%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.38%	97.36%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.32%	86.92%
CHEMBL4208	P20618	Proteasome component C5	84.92%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.34%	99.15%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	81.87%	97.53%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.84%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.26%	95.89%

Plants that contains it

• Callicarpa macrophylla
• Cistanche deserticola
• Cistanche phelypaea
• Phlomoides rotata

Cross-Links

• PubChem: 10009317
• NPASS: NPC197503