(-)-Ajugachin A

Details

• Internal ID: 6a2942de-030d-43f0-8cad-3952cef422b0
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
• IUPAC Name: [(2S,3R,4aR,5S,6R,8S,8aR)-5-[(3aS,6aS)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-5-yl]-8-acetyloxy-8a-(acetyloxymethyl)-3-hydroxy-5,6-dimethylspiro[3,4,4a,6,7,8-hexahydro-2H-naphthalene-1,2'-oxirane]-2-yl] 2-methylpropanoate
• SMILES (Canonical): CC1CC(C2(C(C1(C)C3CC4C=COC4O3)CC(C(C25CO5)OC(=O)C(C)C)O)COC(=O)C)OC(=O)C
• SMILES (Isomeric): C[C@@H]1C[C@@H]([C@@]2([C@@H]([C@@]1(C)C3C[C@H]4C=CO[C@H]4O3)C[C@H]([C@@H](C25CO5)OC(=O)C(C)C)O)COC(=O)C)OC(=O)C
• InChI: InChI=1S/C28H40O10/c1-14(2)24(32)38-23-19(31)11-20-26(6,21-10-18-7-8-33-25(18)37-21)15(3)9-22(36-17(5)30)27(20,12-34-16(4)29)28(23)13-35-28/h7-8,14-15,18-23,25,31H,9-13H2,1-6H3/t15-,18-,19-,20-,21?,22+,23+,25+,26+,27+,28?/m1/s1
• InChI Key: MZEYOXXDMOFRMK-GUXDWVPKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₀O₁₀
• Molecular Weight: 536.60 g/mol
• Exact Mass: 536.26214747 g/mol
• Topological Polar Surface Area (TPSA): 130.00 Ų
• XlogP: 2.60

Synonyms

• 131086-64-1
• (-)-Ajugachin A
• DTXSID10927072
• Caryoptinol, 2-hydroxy-, 3-(2-methylpropanoate), (2alpha,3beta)-
• 8-(Acetyloxy)-8a-[(acetyloxy)methyl]-3-hydroxy-5,6-dimethyl-5-(2,3,3a,6a-tetrahydrofuro[2,3-b]furan-2-yl)octahydro-2H-spiro[naphthalene-1,2'-oxiran]-2-yl 2-methylpropanoate
• Propanoic acid, 2-methyl-, (1R,2S,3R,4aR,5S,6R,8S,8aR)-8-(acetyloxy)-8a-((acetyloxy)methyl)octahydro-3-hydroxy-5,6-dimethyl-5-((2S,3aS,6aS)-2,3,3a,6a-tetrahydrofuro(2,3-b)furan-2-yl)spiro(naphthalene-1(2H),2'-oxiran)-2-yl ester
• Propanoic acid, 2-methyl-, 8-(acetyloxy)-8a-((acetyloxy)methyl)octahydro-3-hydroxy-5,6-dimethyl-5-(2,3,3a,6a-tetrahydrofuro(2,3-b)furan-2-yl)spiro(naphthalene-1(2H),2'-oxiran)-2-yl ester, (1R-(1alpha,2beta,3alpha,4abeta,5beta2S*,3aS*,6aS*),6alpha,8alpha,8aalpha))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

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	98.71%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.60%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.22%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.65%	91.11%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	93.27%	98.75%
CHEMBL340	P08684	Cytochrome P450 3A4	93.25%	91.19%
CHEMBL2581	P07339	Cathepsin D	92.85%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.98%	85.14%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	91.48%	96.47%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.16%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.24%	86.33%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.19%	82.69%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	87.04%	95.71%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	86.78%	97.21%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.16%	91.07%
CHEMBL2996	Q05655	Protein kinase C delta	85.62%	97.79%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.31%	97.14%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	84.70%	89.05%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.36%	92.62%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.57%	89.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.24%	94.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.48%	96.77%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.58%	95.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.90%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.22%	97.36%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.08%	96.95%

Plants that contains it

• Ajuga chamaepitys
• Ajuga reptans

Cross-Links

• PubChem: 183007
• LOTUS: LTS0070870
• wikiData: Q82901692