Ajugarin I

Details

• Internal ID: 8cbf0e74-669f-4ffc-b16e-13501963bf36
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
• IUPAC Name: [(4R,4aR,5S,7R,8S,8aR)-5-acetyloxy-7,8-dimethyl-8-[2-(5-oxo-2H-furan-3-yl)ethyl]spiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-4a-yl]methyl acetate
• SMILES (Canonical): CC1CC(C2(C(C1(C)CCC3=CC(=O)OC3)CCCC24CO4)COC(=O)C)OC(=O)C
• SMILES (Isomeric): C[C@@H]1C[C@@H]([C@@]2([C@@H]([C@@]1(C)CCC3=CC(=O)OC3)CCC[C@]24CO4)COC(=O)C)OC(=O)C
• InChI: InChI=1S/C24H34O7/c1-15-10-20(31-17(3)26)24(14-29-16(2)25)19(6-5-8-23(24)13-30-23)22(15,4)9-7-18-11-21(27)28-12-18/h11,15,19-20H,5-10,12-14H2,1-4H3/t15-,19-,20+,22+,23+,24+/m1/s1
• InChI Key: RNYBNBANBCQZON-PGQNDPHJSA-N
• Popularity: 40 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₄O₇
• Molecular Weight: 434.50 g/mol
• Exact Mass: 434.23045342 g/mol
• Topological Polar Surface Area (TPSA): 91.40 Ų
• XlogP: 2.90

Synonyms

• 62640-05-5
• Ajugarin-I
• Ajugarin-1
• UNII-29UW6AH176
• 29UW6AH176
• CHEBI:2527
• CHEMBL494606
• 2(5H)-Furanone, 4-(2-(8-(acetyloxy)-8a-((acetyloxy)methyl)octahydro-5,6-dimethylspiro(naphthalene-1(2H),2'-oxiran)-5-yl)ethyl)-, (1R-(1alpha,4abeta,5beta,6alpha,8alpha,8aalpha))-
• C09058
• AC1L5AM1
• ajugarin
• AJUGARIN-I [MI]
• DTXSID40978198
• AKOS040750254
• [(4R,4aR,5S,7R,8S,8aR)-5-acetyloxy-7,8-dimethyl-8-[2-(5-oxo-2H-furan-3-yl)ethyl]spiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-4a-yl]methyl acetate
• Q27105704
• (1R-(1.ALPHA.,4A.BETA.,5.BETA.,6.ALPHA.,8.ALPHA.,8A.ALPHA.))-4-(2-(8-(ACETYLOXY)-8A-((ACETYLOXY)METHYL)OCTAHYDRO-5,6-DIMETHYLSPIRO(NAPHTHALENE-1(2H),2'-OXIRAN)-5-YL)ETHYL)-2(5H)FURANONE
• 2(5H)-FURANONE, 4-(2-((1R,4AR,5S,6R,8S,8AR)-8-(ACETYLOXY)-8A-((ACETYLOXY)METHYL)OCTAHYDRO-5,6-DIMETHYLSPIRO(NAPHTHALENE-1(2H),2'-OXIRAN)-5-YL)ETHYL)-

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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.05%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.04%	96.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	95.18%	82.69%
CHEMBL2581	P07339	Cathepsin D	94.38%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.03%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.80%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.73%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.69%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.06%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.19%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.54%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.01%	99.23%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.13%	92.62%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.05%	93.04%
CHEMBL340	P08684	Cytochrome P450 3A4	82.65%	91.19%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.62%	94.80%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.76%	95.71%
CHEMBL5028	O14672	ADAM10	81.47%	97.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.26%	85.14%

Plants that contains it

• Ajuga integrifolia
• Ajuga nipponensis
• Ajuga parviflora

Cross-Links

• PubChem: 173866
• LOTUS: LTS0223221
• wikiData: Q27105704