Bullatacinone

Details

• Internal ID: 2fe63153-625e-434b-9a0e-34061c956b7a
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty alcohols > Annonaceous acetogenins
• IUPAC Name: (3S,5R)-5-[(11R)-11-hydroxy-11-[(2R,5R)-5-[(2R,5R)-5-[(1S)-1-hydroxyundecyl]oxolan-2-yl]oxolan-2-yl]undecyl]-3-(2-oxopropyl)oxolan-2-one
• SMILES (Canonical): CCCCCCCCCCC(C1CCC(O1)C2CCC(O2)C(CCCCCCCCCCC3CC(C(=O)O3)CC(=O)C)O)O
• SMILES (Isomeric): CCCCCCCCCC[C@@H]([C@H]1CC[C@@H](O1)[C@H]2CC[C@@H](O2)[C@@H](CCCCCCCCCC[C@@H]3C[C@H](C(=O)O3)CC(=O)C)O)O
• InChI: InChI=1S/C37H66O7/c1-3-4-5-6-7-11-14-17-20-31(39)33-22-24-35(43-33)36-25-23-34(44-36)32(40)21-18-15-12-9-8-10-13-16-19-30-27-29(26-28(2)38)37(41)42-30/h29-36,39-40H,3-27H2,1-2H3/t29-,30-,31+,32-,33-,34-,35-,36-/m1/s1
• InChI Key: KGGVWMAPBXIMEM-ZRTAFWODSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₆₆O₇
• Molecular Weight: 622.90 g/mol
• Exact Mass: 622.48085444 g/mol
• Topological Polar Surface Area (TPSA): 102.00 Ų
• XlogP: 9.40
• Atomic LogP (AlogP): 8.15
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 25

Synonyms

• AC1L9BBA
• C08470
• 123012-00-0
• CHEBI:3212
• DTXSID201317707
• (3S,5R)-3-acetonyl-5-[(11R)-11-hydroxy-11-[(2R,5R)-5-[(2R,5R)-5-[(1S)-1-hydroxyundecyl]tetrahydrofuran-2-yl]tetrahydrofuran-2-yl]undecyl]tetrahydrofuran-2-one
• (3S,5R)-5-[(11R)-11-hydroxy-11-[(2R,5R)-5-[(2R,5R)-5-[(1S)-1-hydroxyundecyl]oxolan-2-yl]oxolan-2-yl]undecyl]-3-(2-oxopropyl)oxolan-2-one
• Q27105994

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9255	92.55%
Caco-2	-	0.8177	81.77%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8280	82.80%
OATP2B1 inhibitior	-	0.5613	56.13%
OATP1B1 inhibitior	+	0.8897	88.97%
OATP1B3 inhibitior	+	0.8869	88.69%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6407	64.07%
P-glycoprotein inhibitior	+	0.6501	65.01%
P-glycoprotein substrate	+	0.5760	57.60%
CYP3A4 substrate	+	0.6178	61.78%
CYP2C9 substrate	-	0.7891	78.91%
CYP2D6 substrate	-	0.8505	85.05%
CYP3A4 inhibition	-	0.7396	73.96%
CYP2C9 inhibition	-	0.8891	88.91%
CYP2C19 inhibition	-	0.8418	84.18%
CYP2D6 inhibition	-	0.9377	93.77%
CYP1A2 inhibition	-	0.8500	85.00%
CYP2C8 inhibition	-	0.6782	67.82%
CYP inhibitory promiscuity	-	0.9621	96.21%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6971	69.71%
Eye corrosion	-	0.9853	98.53%
Eye irritation	-	0.8101	81.01%
Skin irritation	-	0.6506	65.06%
Skin corrosion	-	0.9052	90.52%
Ames mutagenesis	-	0.8437	84.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4560	45.60%
Micronuclear	-	0.9300	93.00%
Hepatotoxicity	+	0.5513	55.13%
skin sensitisation	-	0.9027	90.27%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.5535	55.35%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.8225	82.25%
Acute Oral Toxicity (c)	III	0.5296	52.96%
Estrogen receptor binding	+	0.7517	75.17%
Androgen receptor binding	+	0.6499	64.99%
Thyroid receptor binding	-	0.6547	65.47%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.5405	54.05%
PPAR gamma	+	0.5396	53.96%
Honey bee toxicity	-	0.9269	92.69%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	+	0.6328	63.28%
Fish aquatic toxicity	+	0.9533	95.33%

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	97.57%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.01%	97.25%
CHEMBL2581	P07339	Cathepsin D	93.41%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.71%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.51%	91.11%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	90.56%	85.94%
CHEMBL4462	Q8IXJ6	NAD-dependent deacetylase sirtuin 2	90.43%	90.24%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	89.65%	100.00%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	89.15%	97.29%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.95%	97.09%
CHEMBL5255	O00206	Toll-like receptor 4	85.64%	92.50%
CHEMBL5103	Q969S8	Histone deacetylase 10	84.02%	90.08%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	83.41%	96.47%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.11%	94.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.08%	89.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.97%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	82.84%	94.73%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.54%	93.56%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	82.43%	98.33%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	82.36%	80.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.35%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.06%	95.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.88%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	81.87%	91.19%
CHEMBL230	P35354	Cyclooxygenase-2	81.85%	89.63%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	80.72%	95.00%
CHEMBL1944495	P28065	Proteasome subunit beta type-9	80.69%	97.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.45%	95.89%

Plants that contains it

• Annona bullata
• Annona cherimola
• Annona reticulata
• Annona squamosa

Cross-Links

• PubChem: 441557
• LOTUS: LTS0003387
• wikiData: Q27105994