Decaffeoyl-acteoside

Details

• Internal ID: dbedd613-6160-433b-8edf-b3ee614f0cbf
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: 2-[2-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(OC(C2O)OCCC3=CC(=C(C=C3)O)O)CO)O)O)O)O
• SMILES (Isomeric): CC1C(C(C(C(O1)OC2C(C(OC(C2O)OCCC3=CC(=C(C=C3)O)O)CO)O)O)O)O
• InChI: InChI=1S/C20H30O12/c1-8-13(24)15(26)16(27)20(30-8)32-18-14(25)12(7-21)31-19(17(18)28)29-5-4-9-2-3-10(22)11(23)6-9/h2-3,6,8,12-28H,4-5,7H2,1H3
• InChI Key: DORPKYRPJIIARM-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₁₂
• Molecular Weight: 462.40 g/mol
• Exact Mass: 462.17372639 g/mol
• Topological Polar Surface Area (TPSA): 199.00 Ų
• XlogP: -1.90
• Atomic LogP (AlogP): -2.69
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

• Decaffeoylverbascoside
• 2-[2-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-6-methyloxane-3,4,5-triol
• Dicaffeoylacteoside
• NSC729651
• NSC-729651

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8726	87.26%
Caco-2	-	0.8774	87.74%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7778	77.78%
OATP2B1 inhibitior	-	0.8642	86.42%
OATP1B1 inhibitior	+	0.9064	90.64%
OATP1B3 inhibitior	+	0.9547	95.47%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.7336	73.36%
P-glycoprotein inhibitior	-	0.8645	86.45%
P-glycoprotein substrate	-	0.7647	76.47%
CYP3A4 substrate	+	0.5737	57.37%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8110	81.10%
CYP3A4 inhibition	-	0.9563	95.63%
CYP2C9 inhibition	-	0.7235	72.35%
CYP2C19 inhibition	-	0.8765	87.65%
CYP2D6 inhibition	-	0.9295	92.95%
CYP1A2 inhibition	-	0.8773	87.73%
CYP2C8 inhibition	+	0.4893	48.93%
CYP inhibitory promiscuity	-	0.7558	75.58%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6351	63.51%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9404	94.04%
Skin irritation	-	0.8274	82.74%
Skin corrosion	-	0.9571	95.71%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6917	69.17%
Micronuclear	-	0.7241	72.41%
Hepatotoxicity	-	0.9375	93.75%
skin sensitisation	-	0.8630	86.30%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	-	0.5444	54.44%
Mitochondrial toxicity	-	0.8125	81.25%
Nephrotoxicity	-	0.8608	86.08%
Acute Oral Toxicity (c)	III	0.7338	73.38%
Estrogen receptor binding	+	0.5520	55.20%
Androgen receptor binding	-	0.5629	56.29%
Thyroid receptor binding	+	0.6463	64.63%
Glucocorticoid receptor binding	-	0.6159	61.59%
Aromatase binding	+	0.6480	64.80%
PPAR gamma	+	0.6776	67.76%
Honey bee toxicity	-	0.7045	70.45%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5150	51.50%
Fish aquatic toxicity	-	0.6581	65.81%

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	99.42%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.52%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.95%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.87%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.05%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	91.60%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.29%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.28%	99.17%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.56%	97.36%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.38%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.49%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.73%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	82.56%	95.93%
CHEMBL3194	P02766	Transthyretin	81.67%	90.71%
CHEMBL4208	P20618	Proteasome component C5	81.52%	90.00%

Plants that contains it

• Barleria strigosa
• Buddleja officinalis
• Callicarpa macrophylla
• Carex distachya
• Chelone obliqua
• Dolichandrone serrulata
• Euphrasia nemorosa
• Fernandoa adenophylla
• Globularia dumulosa
• Markhamia stipulata
• Pedicularis striata
• Premna odorata
• Ruellia patula
• Santisukia kerrii
• Scrophularia buergeriana
• Scrophularia ningpoensis
• Sesamum indicum
• Stachys byzantina
• Stereospermum cylindricum
• Volkameria inermis

Cross-Links

• PubChem: 13889681
• NPASS: NPC258320
• LOTUS: LTS0074351
• wikiData: Q104397541