Ajugalide B

Details

• Internal ID: 67f665e2-4937-42c7-902d-070ee5bbe9a5
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tetracarboxylic acids and derivatives
• IUPAC Name: [(1R,4R,4aR,5S,7R,8S,8aR)-1,5-diacetyloxy-8-[(2S)-2-hydroxy-2-(5-oxo-2H-furan-3-yl)ethyl]-7,8-dimethylspiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-4a-yl]methyl acetate
• SMILES (Canonical): CC1CC(C2(C(C1(C)CC(C3=CC(=O)OC3)O)C(CCC24CO4)OC(=O)C)COC(=O)C)OC(=O)C
• SMILES (Isomeric): C[C@@H]1C[C@@H]([C@@]2([C@@H]([C@@]1(C)C[C@@H](C3=CC(=O)OC3)O)[C@@H](CC[C@]24CO4)OC(=O)C)COC(=O)C)OC(=O)C
• InChI: InChI=1S/C26H36O10/c1-14-8-21(36-17(4)29)26(13-33-15(2)27)23(20(35-16(3)28)6-7-25(26)12-34-25)24(14,5)10-19(30)18-9-22(31)32-11-18/h9,14,19-21,23,30H,6-8,10-13H2,1-5H3/t14-,19+,20-,21+,23-,24+,25+,26-/m1/s1
• InChI Key: MBBUQNSETPVJDQ-KOOOSSTKSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₆O₁₀
• Molecular Weight: 508.60 g/mol
• Exact Mass: 508.23084734 g/mol
• Topological Polar Surface Area (TPSA): 138.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.86
• H-Bond Acceptor: 10
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

• CHEBI:69886
• CHEMBL1813873
• Q27138230
• (1R,4R,4aR,5S,6R,8S,8aR)-8a-[(acetyloxy)methyl]-5-[(2S)-2-hydroxy-2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-5,6-dimethyloctahydro-2H-spiro[naphthalene-1,2'-oxirane]-4,8-diyl diacetate
• [(1R,4R,4aR,5S,7R,8S,8aR)-1,5-diacetyloxy-8-[(2S)-2-hydroxy-2-(5-oxo-2H-furan-3-yl)ethyl]-7,8-dimethylspiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-4a-yl]methyl acetate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9877	98.77%
Caco-2	-	0.6542	65.42%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8133	81.33%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8813	88.13%
OATP1B3 inhibitior	+	0.9481	94.81%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6021	60.21%
BSEP inhibitior	+	0.9104	91.04%
P-glycoprotein inhibitior	+	0.7613	76.13%
P-glycoprotein substrate	+	0.6046	60.46%
CYP3A4 substrate	+	0.6882	68.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8932	89.32%
CYP3A4 inhibition	-	0.6777	67.77%
CYP2C9 inhibition	-	0.7193	71.93%
CYP2C19 inhibition	-	0.8788	87.88%
CYP2D6 inhibition	-	0.9441	94.41%
CYP1A2 inhibition	-	0.8733	87.33%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.9317	93.17%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5120	51.20%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9187	91.87%
Skin irritation	-	0.5575	55.75%
Skin corrosion	-	0.9330	93.30%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6720	67.20%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	-	0.6101	61.01%
skin sensitisation	-	0.8636	86.36%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.5147	51.47%
Acute Oral Toxicity (c)	I	0.5172	51.72%
Estrogen receptor binding	+	0.8846	88.46%
Androgen receptor binding	+	0.7212	72.12%
Thyroid receptor binding	+	0.5345	53.45%
Glucocorticoid receptor binding	+	0.8309	83.09%
Aromatase binding	+	0.7276	72.76%
PPAR gamma	+	0.6476	64.76%
Honey bee toxicity	-	0.7090	70.90%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9883	98.83%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.81%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.36%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.15%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.98%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.67%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.84%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.32%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.46%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	90.31%	82.69%
CHEMBL3922	P50579	Methionine aminopeptidase 2	87.98%	97.28%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.62%	89.00%
CHEMBL221	P23219	Cyclooxygenase-1	86.77%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.11%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.90%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	83.61%	91.19%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	83.06%	94.80%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.44%	89.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.94%	99.23%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.39%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.05%	99.17%
CHEMBL5028	O14672	ADAM10	80.76%	97.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.70%	86.33%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.45%	94.33%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.26%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.04%	91.07%

Plants that contains it

• Ajuga ciliata
• Ajuga taiwanensis

Cross-Links

• PubChem: 12136678
• LOTUS: LTS0267157
• wikiData: Q27138230