[(1S)-2-[(1S,2R,4S,4aR,8R,8aR)-4-acetyloxy-4a-(acetyloxymethyl)-1,2-dimethyl-8-[(E)-2-methylbut-2-enoyl]oxyspiro[3,4,6,7,8,8a-hexahydro-2H-naphthalene-5,2'-oxirane]-1-yl]-1-(5-oxo-2H-furan-3-yl)ethyl] (2S)-2-methylbutanoate

Details

• Internal ID: 820041db-f88e-4937-9d8e-8e38ffd3f7f6
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Pentacarboxylic acids and derivatives
• IUPAC Name: [(1S)-2-[(1S,2R,4S,4aR,8R,8aR)-4-acetyloxy-4a-(acetyloxymethyl)-1,2-dimethyl-8-[(E)-2-methylbut-2-enoyl]oxyspiro[3,4,6,7,8,8a-hexahydro-2H-naphthalene-5,2'-oxirane]-1-yl]-1-(5-oxo-2H-furan-3-yl)ethyl] (2S)-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC(CC1(C(CC(C2(C1C(CCC23CO3)OC(=O)C(=CC)C)COC(=O)C)OC(=O)C)C)C)C4=CC(=O)OC4
• SMILES (Isomeric): CC[C@H](C)C(=O)O[C@@H](C[C@]1([C@@H](C[C@@H]([C@@]2([C@@H]1[C@@H](CCC23CO3)OC(=O)/C(=C/C)/C)COC(=O)C)OC(=O)C)C)C)C4=CC(=O)OC4
• InChI: InChI=1S/C34H48O11/c1-9-19(3)30(38)44-25-11-12-33(17-42-33)34(18-41-22(6)35)27(43-23(7)36)13-21(5)32(8,29(25)34)15-26(24-14-28(37)40-16-24)45-31(39)20(4)10-2/h9,14,20-21,25-27,29H,10-13,15-18H2,1-8H3/b19-9+/t20-,21+,25+,26-,27-,29+,32-,33?,34+/m0/s1
• InChI Key: JTNPKPFJZRMAJE-OMMMTVEPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₈O₁₁
• Molecular Weight: 632.70 g/mol
• Exact Mass: 632.31966234 g/mol
• Topological Polar Surface Area (TPSA): 144.00 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 4.40
• H-Bond Acceptor: 11
• H-Bond Donor: 0
• Rotatable Bonds: 11

Synonyms

• 122587-83-1
• Ajugamarin G 1
• 2-Butenoic acid, 2-methyl-, 8-(acetyloxy)-8a-((acetyloxy)methyl)-5-(2-(2,5-dihydro-5-oxo-3-furanyl)-2-(2-methyl-1-oxobutoxy)ethyl)octahydro-5,6-dimethylspiro(naphthalene-1(2H),2'-oxiran)-4-yl ester, (1R-(1alpha,4beta(E),4abeta,5beta(S*(S*)),6alpha,8alpha,8aalpha))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9910	99.10%
Caco-2	-	0.7591	75.91%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7421	74.21%
OATP2B1 inhibitior	-	0.7221	72.21%
OATP1B1 inhibitior	+	0.8314	83.14%
OATP1B3 inhibitior	+	0.9687	96.87%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.9936	99.36%
P-glycoprotein inhibitior	+	0.8832	88.32%
P-glycoprotein substrate	+	0.6962	69.62%
CYP3A4 substrate	+	0.7051	70.51%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8993	89.93%
CYP3A4 inhibition	-	0.7113	71.13%
CYP2C9 inhibition	-	0.7934	79.34%
CYP2C19 inhibition	-	0.7359	73.59%
CYP2D6 inhibition	-	0.9202	92.02%
CYP1A2 inhibition	-	0.7900	79.00%
CYP2C8 inhibition	+	0.6128	61.28%
CYP inhibitory promiscuity	-	0.6954	69.54%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4988	49.88%
Eye corrosion	-	0.9860	98.60%
Eye irritation	-	0.9092	90.92%
Skin irritation	-	0.5929	59.29%
Skin corrosion	-	0.9271	92.71%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7683	76.83%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	+	0.5149	51.49%
skin sensitisation	-	0.8423	84.23%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.6456	64.56%
Acute Oral Toxicity (c)	III	0.5143	51.43%
Estrogen receptor binding	+	0.8460	84.60%
Androgen receptor binding	+	0.7403	74.03%
Thyroid receptor binding	+	0.5754	57.54%
Glucocorticoid receptor binding	+	0.8251	82.51%
Aromatase binding	+	0.7219	72.19%
PPAR gamma	+	0.7253	72.53%
Honey bee toxicity	-	0.6315	63.15%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9961	99.61%

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	98.53%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.82%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.81%	94.45%
CHEMBL2581	P07339	Cathepsin D	97.74%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.54%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	94.54%	90.17%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	93.82%	82.69%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.69%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.19%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.01%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.74%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.05%	86.33%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	87.28%	94.80%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.64%	95.89%
CHEMBL2413	P32246	C-C chemokine receptor type 1	85.47%	89.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.16%	92.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.86%	99.23%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.24%	97.28%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.87%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	83.60%	94.75%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.00%	96.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.54%	94.33%
CHEMBL5255	O00206	Toll-like receptor 4	81.36%	92.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.23%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.25%	91.07%

Plants that contains it

• Ajuga decumbens

Cross-Links

• PubChem: 6442444
• LOTUS: LTS0053778
• wikiData: Q105134874