Ajubractin D

Details

• Internal ID: 0cb182d1-cc09-49b1-8c05-8c3a518bcc72
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
• IUPAC Name: [(1R,2S,3R,4aR,5S,6R,8S,8aR)-5-[(3aR,5S,6aS)-2,3,3a,4,5,6a-hexahydrofuro[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)C3CC4CCOC4O3)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)[C@@H]3C[C@H]4CCO[C@H]4O3)C[C@H]([C@@H]([C@]25CO5)OC(=O)C(C)C)O)COC(=O)C)OC(=O)C
• InChI: InChI=1S/C28H42O10/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/h14-15,18-23,25,31H,7-13H2,1-6H3/t15-,18-,19-,20-,21+,22+,23+,25+,26+,27+,28-/m1/s1
• InChI Key: GDRNWAABIDILBN-QOAKXUCVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₂O₁₀
• Molecular Weight: 538.60 g/mol
• Exact Mass: 538.27779753 g/mol
• Topological Polar Surface Area (TPSA): 130.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.38
• H-Bond Acceptor: 10
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• 14,15-dihydroajugachin A
• CHEBI:67460
• Q27135928
• 3beta-isobutyryloxy-2alpha-hydroxy-14,15-dihydroclerodin
• (1R,2S,3R,4aR,5S,6R,8S,8aR)-8-(acetyloxy)-8a-[(acetyloxy)methyl]-5-[(2S,3aR,6aS)-hexahydrofuro[2,3-b]furan-2-yl]-3-hydroxy-5,6-dimethyloctahydro-2H-spiro[naphthalene-1,2'-oxiran]-2-yl 2-methylpropanoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9562	95.62%
Caco-2	-	0.7097	70.97%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8245	82.45%
OATP2B1 inhibitior	-	0.8588	85.88%
OATP1B1 inhibitior	+	0.8642	86.42%
OATP1B3 inhibitior	+	0.8851	88.51%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.7269	72.69%
P-glycoprotein inhibitior	+	0.6487	64.87%
P-glycoprotein substrate	+	0.5542	55.42%
CYP3A4 substrate	+	0.6883	68.83%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8535	85.35%
CYP3A4 inhibition	-	0.6086	60.86%
CYP2C9 inhibition	-	0.6893	68.93%
CYP2C19 inhibition	-	0.7761	77.61%
CYP2D6 inhibition	-	0.9501	95.01%
CYP1A2 inhibition	-	0.9339	93.39%
CYP2C8 inhibition	+	0.5137	51.37%
CYP inhibitory promiscuity	-	0.9322	93.22%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5117	51.17%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.9000	90.00%
Skin irritation	-	0.6606	66.06%
Skin corrosion	-	0.9343	93.43%
Ames mutagenesis	-	0.5037	50.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5910	59.10%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.8921	89.21%
Respiratory toxicity	-	0.6444	64.44%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.6621	66.21%
Acute Oral Toxicity (c)	I	0.5882	58.82%
Estrogen receptor binding	+	0.8356	83.56%
Androgen receptor binding	+	0.7016	70.16%
Thyroid receptor binding	-	0.5369	53.69%
Glucocorticoid receptor binding	+	0.7205	72.05%
Aromatase binding	+	0.7125	71.25%
PPAR gamma	+	0.7270	72.70%
Honey bee toxicity	-	0.7219	72.19%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6355	63.55%
Fish aquatic toxicity	+	0.9708	97.08%

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	98.54%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.77%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.44%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.17%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.40%	85.14%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	94.08%	98.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.98%	97.09%
CHEMBL2581	P07339	Cathepsin D	93.92%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	93.44%	91.19%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	91.83%	96.47%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	90.24%	89.05%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.81%	82.69%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	88.60%	91.07%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	87.95%	95.71%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.58%	92.62%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.85%	96.77%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.64%	94.33%
CHEMBL2996	Q05655	Protein kinase C delta	85.56%	97.79%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.00%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.25%	89.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.10%	89.50%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.95%	97.28%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.56%	86.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.38%	95.50%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	82.09%	82.50%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	82.03%	91.65%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.94%	95.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.81%	100.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.59%	94.80%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.39%	95.89%

Plants that contains it

• Ajuga reptans

Cross-Links

• PubChem: 53355578
• NPASS: NPC699
• LOTUS: LTS0021109
• wikiData: Q27135928