Ajubractin E

Details

• Internal ID: 65dc1ec6-2ade-4389-aa99-e4253e144b40
• Taxonomy: Organoheterocyclic compounds > Furofurans
• IUPAC Name: [(3S,4R,4aR,5S,7R,8S,8aR)-8-[(3aR,5S,6aS)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-5-yl]-5-acetyloxy-3-hydroxy-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)C3CC4CCOC4O3)CCC(C25CO5)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)CC[C@@H]([C@]25CO5)O)COC(=O)C)OC(=O)C
• InChI: InChI=1S/C24H36O8/c1-13-9-20(31-15(3)26)23(11-29-14(2)25)17(5-6-18(27)24(23)12-30-24)22(13,4)19-10-16-7-8-28-21(16)32-19/h13,16-21,27H,5-12H2,1-4H3/t13-,16-,17-,18+,19+,20+,21+,22+,23+,24-/m1/s1
• InChI Key: YGOONLMJIAXMBW-PVSOBBEXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₆O₈
• Molecular Weight: 452.50 g/mol
• Exact Mass: 452.24101810 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.21
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• CHEBI:67468
• 3-epi-14,15-dihydrocaryoptinol
• 3beta-hydroxy-14,15-dihydroclerodin
• {(1R,2S,4aR,5S,6R,8S,8aR)-8-(acetyloxy)-5-[(2S,3aR,6aS)-hexahydrofuro[2,3-b]furan-2-yl]-2-hydroxy-5,6-dimethyloctahydro-8aH-spiro[naphthalene-1,2'-oxiran]-8a-yl}methyl acetate
• ((1R,2S,4aR,5S,6R,8S,8aR)-8-(acetyloxy)-5-((2S,3aR,6aS)-hexahydrofuro(2,3-b)furan-2-yl)-2-hydroxy-5,6-dimethyloctahydro-8aH-spiro(naphthalene-1,2'-oxiran)-8a-yl)methyl acetate
• ((3S,4R,4aR,5S,7R,8S,8aR)-8-((3aR,5S,6aS)-2,3,3a,4,5,6a-hexahydrofuro(2,3-b)furan-5-yl)-5-acetyloxy-3-hydroxy-7,8-dimethylspiro(2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane)-4a-yl)methyl acetate
• [(3S,4R,4aR,5S,7R,8S,8aR)-8-[(3aR,5S,6aS)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-5-yl]-5-acetyloxy-3-hydroxy-7,8-dimethylspiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-4a-yl]methyl acetate
• RefChem:110322
• 3b-Hydroxy-14,15-dihydroclerodin
• Q27135935

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9632	96.32%
Caco-2	-	0.6442	64.42%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8233	82.33%
OATP2B1 inhibitior	-	0.8631	86.31%
OATP1B1 inhibitior	+	0.8812	88.12%
OATP1B3 inhibitior	+	0.8906	89.06%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7287	72.87%
BSEP inhibitior	+	0.5554	55.54%
P-glycoprotein inhibitior	-	0.5682	56.82%
P-glycoprotein substrate	+	0.5072	50.72%
CYP3A4 substrate	+	0.6954	69.54%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8535	85.35%
CYP3A4 inhibition	-	0.5720	57.20%
CYP2C9 inhibition	-	0.7008	70.08%
CYP2C19 inhibition	-	0.7655	76.55%
CYP2D6 inhibition	-	0.9584	95.84%
CYP1A2 inhibition	-	0.9230	92.30%
CYP2C8 inhibition	+	0.6171	61.71%
CYP inhibitory promiscuity	-	0.9385	93.85%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5380	53.80%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9180	91.80%
Skin irritation	-	0.6399	63.99%
Skin corrosion	-	0.9370	93.70%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5959	59.59%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.9262	92.62%
Respiratory toxicity	-	0.7000	70.00%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.5243	52.43%
Acute Oral Toxicity (c)	I	0.5846	58.46%
Estrogen receptor binding	+	0.8803	88.03%
Androgen receptor binding	+	0.6374	63.74%
Thyroid receptor binding	+	0.5670	56.70%
Glucocorticoid receptor binding	+	0.7363	73.63%
Aromatase binding	+	0.7819	78.19%
PPAR gamma	+	0.7227	72.27%
Honey bee toxicity	-	0.7994	79.94%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5387	53.87%
Fish aquatic toxicity	+	0.9661	96.61%

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	98.20%	96.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	93.84%	96.95%
CHEMBL2581	P07339	Cathepsin D	93.62%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.16%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.36%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.77%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.16%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	88.61%	91.19%
CHEMBL3922	P50579	Methionine aminopeptidase 2	88.27%	97.28%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	87.20%	89.05%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.95%	94.45%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.66%	94.33%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	84.58%	97.21%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.55%	85.14%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.40%	95.50%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	84.14%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.65%	82.69%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.95%	99.17%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.29%	96.77%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	81.62%	95.71%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.59%	94.80%
CHEMBL2996	Q05655	Protein kinase C delta	81.38%	97.79%
CHEMBL5255	O00206	Toll-like receptor 4	81.02%	92.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.79%	100.00%
CHEMBL5028	O14672	ADAM10	80.02%	97.50%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 53355682
• NPASS: NPC249300
• LOTUS: LTS0225081
• wikiData: Q27135935