Ajugalide C

Details

• Internal ID: fcc4d841-d462-4069-ae05-fa22181a7f1f
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
• IUPAC Name: [(4R,4aR,5S,7R,8S,8aR)-5-acetyloxy-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)CCCC24CO4)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)CCC[C@]24CO4)COC(=O)C)OC(=O)C
• InChI: InChI=1S/C24H34O8/c1-14-8-20(32-16(3)26)24(13-30-15(2)25)19(6-5-7-23(24)12-31-23)22(14,4)10-18(27)17-9-21(28)29-11-17/h9,14,18-20,27H,5-8,10-13H2,1-4H3/t14-,18+,19-,20+,22+,23+,24+/m1/s1
• InChI Key: DSTKFVXVQRVYIH-VQSMGOMNSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₄O₈
• Molecular Weight: 450.50 g/mol
• Exact Mass: 450.22536804 g/mol
• Topological Polar Surface Area (TPSA): 112.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.32
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• CHEBI:69882
• CHEMBL1813870
• AKOS040734240
• 853247-64-0
• Q27138226
• [(4R,4aR,5S,7R,8S,8aR)-5-acetyloxy-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
• {(1R,4aR,5S,6R,8S,8aR)-8-(acetyloxy)-5-[(2S)-2-hydroxy-2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-5,6-dimethyloctahydro-8aH-spiro[naphthalene-1,2'-oxiran]-8a-yl}methyl acetate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9877	98.77%
Caco-2	-	0.6341	63.41%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8133	81.33%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8644	86.44%
OATP1B3 inhibitior	+	0.9481	94.81%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6021	60.21%
BSEP inhibitior	+	0.7356	73.56%
P-glycoprotein inhibitior	+	0.6105	61.05%
P-glycoprotein substrate	+	0.5366	53.66%
CYP3A4 substrate	+	0.6814	68.14%
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	+	0.4583	45.83%
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	-	0.9123	91.23%
Skin irritation	-	0.5575	55.75%
Skin corrosion	-	0.9330	93.30%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6971	69.71%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	-	0.5941	59.41%
skin sensitisation	-	0.8636	86.36%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.4675	46.75%
Acute Oral Toxicity (c)	I	0.5172	51.72%
Estrogen receptor binding	+	0.9043	90.43%
Androgen receptor binding	+	0.6890	68.90%
Thyroid receptor binding	+	0.5348	53.48%
Glucocorticoid receptor binding	+	0.8390	83.90%
Aromatase binding	+	0.7721	77.21%
PPAR gamma	+	0.6233	62.33%
Honey bee toxicity	-	0.7303	73.03%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
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	98.37%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.93%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.28%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.07%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.57%	85.14%
CHEMBL2581	P07339	Cathepsin D	95.90%	98.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	94.52%	82.69%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.25%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.69%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.11%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.47%	95.89%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	86.40%	86.00%
CHEMBL340	P08684	Cytochrome P450 3A4	86.22%	91.19%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	86.03%	94.80%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.76%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.73%	92.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.52%	99.23%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.26%	93.04%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.16%	100.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.05%	89.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.54%	86.33%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	82.16%	83.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.14%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	81.99%	92.50%
CHEMBL5028	O14672	ADAM10	80.59%	97.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.59%	94.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.18%	91.07%

Plants that contains it

• Ajuga ciliata
• Ajuga taiwanensis
• Teucrium massiliense

Cross-Links

• PubChem: 12136679
• LOTUS: LTS0275333
• wikiData: Q27138226