6-O-Vanilloylajugol

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	4d99cc19-8210-4df5-ba62-e8b7e196aece
Taxonomy	Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
IUPAC Name	[(1S,4aR,5R,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5-yl] 4-hydroxy-3-methoxybenzoate
SMILES (Canonical)	CC1(CC(C2C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)OC(=O)C4=CC(=C(C=C4)O)OC)O
SMILES (Isomeric)	C[C@@]1(C[C@H]([C@H]2[C@@H]1[C@@H](OC=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)OC(=O)C4=CC(=C(C=C4)O)OC)O
InChI	InChI=1S/C23H30O12/c1-23(30)8-14(33-20(29)10-3-4-12(25)13(7-10)31-2)11-5-6-32-21(16(11)23)35-22-19(28)18(27)17(26)15(9-24)34-22/h3-7,11,14-19,21-22,24-28,30H,8-9H2,1-2H3/t11-,14+,15+,16+,17+,18-,19+,21-,22-,23-/m0/s1
InChI Key	PJAISAAYEQAVGA-YYFWYDPZSA-N
Popularity	1 reference in papers

Physical and Chemical Properties

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Molecular Formula	C₂₃H₃₀O₁₂
Molecular Weight	498.50 g/mol
Exact Mass	498.17372639 g/mol
Topological Polar Surface Area (TPSA)	185.00 Å²
XlogP	-0.30
Atomic LogP (AlogP)	-1.00
H-Bond Acceptor	12
H-Bond Donor	6
Rotatable Bonds	6

Synonyms

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124168-04-3

[(1S,4aR,5R,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5-yl] 4-hydroxy-3-methoxybenzoate

6-Vanilloylajugol

6-O-Vanilloyl Ajugol

CHEMBL1779142

AKOS032962449

(1S,4aR,5R,7S,7aS)-1,4a,5,6,7,7a-Hexahydro-7-hydroxy-5-[(4-hydroxy-3-methoxybenzoyl)oxy]-7-methylcyclopenta[c]pyran-1-yl -D-glucopyranoside

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7567	75.67%
Caco-2	-	0.8775	87.75%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5174	51.74%
OATP2B1 inhibitior	-	0.8610	86.10%
OATP1B1 inhibitior	+	0.8387	83.87%
OATP1B3 inhibitior	+	0.9544	95.44%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6411	64.11%
P-glycoprotein inhibitior	-	0.6334	63.34%
P-glycoprotein substrate	-	0.5822	58.22%
CYP3A4 substrate	+	0.6823	68.23%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8488	84.88%
CYP3A4 inhibition	-	0.7980	79.80%
CYP2C9 inhibition	-	0.9250	92.50%
CYP2C19 inhibition	-	0.8799	87.99%
CYP2D6 inhibition	-	0.8572	85.72%
CYP1A2 inhibition	-	0.8165	81.65%
CYP2C8 inhibition	+	0.7110	71.10%
CYP inhibitory promiscuity	-	0.8378	83.78%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5976	59.76%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9440	94.40%
Skin irritation	-	0.7681	76.81%
Skin corrosion	-	0.9398	93.98%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4249	42.49%
Micronuclear	-	0.5226	52.26%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.8298	82.98%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.7818	78.18%
Acute Oral Toxicity (c)	III	0.5478	54.78%
Estrogen receptor binding	+	0.7631	76.31%
Androgen receptor binding	-	0.5524	55.24%
Thyroid receptor binding	+	0.5617	56.17%
Glucocorticoid receptor binding	+	0.6459	64.59%
Aromatase binding	+	0.5462	54.62%
PPAR gamma	+	0.6755	67.55%
Honey bee toxicity	-	0.7929	79.29%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6915	69.15%
Fish aquatic toxicity	+	0.8121	81.21%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
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	99.47%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.77%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.06%	86.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	93.45%	96.21%
CHEMBL4208	P20618	Proteasome component C5	92.75%	90.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	92.55%	92.94%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.80%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.36%	94.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.26%	96.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.26%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.74%	89.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	87.23%	95.83%
CHEMBL3194	P02766	Transthyretin	87.04%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.67%	95.56%
CHEMBL220	P22303	Acetylcholinesterase	85.59%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.21%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.50%	96.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.27%	92.62%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.67%	97.21%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.64%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.26%	97.14%
CHEMBL2535	P11166	Glucose transporter	80.11%	98.75%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.