3-[(13S)-2,13-dihydroxy-13-[(2S,5R)-5-[(1R,4S,5R)-1,4,5-trihydroxypentadecyl]oxolan-2-yl]tridecyl]-5-hydroxy-5-methylfuran-2-one

Details

• Internal ID: e7bdabc4-1b3e-4734-a9a8-46830854bf78
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty alcohols > Annonaceous acetogenins
• IUPAC Name: 3-[(13S)-2,13-dihydroxy-13-[(2S,5R)-5-[(1R,4S,5R)-1,4,5-trihydroxypentadecyl]oxolan-2-yl]tridecyl]-5-hydroxy-5-methylfuran-2-one
• SMILES (Canonical): CCCCCCCCCCC(C(CCC(C1CCC(O1)C(CCCCCCCCCCC(CC2=CC(OC2=O)(C)O)O)O)O)O)O
• SMILES (Isomeric): CCCCCCCCCC[C@H]([C@H](CC[C@H]([C@H]1CC[C@H](O1)[C@H](CCCCCCCCCCC(CC2=CC(OC2=O)(C)O)O)O)O)O)O
• InChI: InChI=1S/C37H68O9/c1-3-4-5-6-7-11-14-17-20-30(39)31(40)22-23-33(42)35-25-24-34(45-35)32(41)21-18-15-12-9-8-10-13-16-19-29(38)26-28-27-37(2,44)46-36(28)43/h27,29-35,38-42,44H,3-26H2,1-2H3/t29?,30-,31+,32+,33-,34+,35-,37?/m1/s1
• InChI Key: USIUGLRYYKXESD-ARCPNRSESA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₆₈O₉
• Molecular Weight: 656.90 g/mol
• Exact Mass: 656.48633374 g/mol
• Topological Polar Surface Area (TPSA): 157.00 Ų
• XlogP: 7.90
• Atomic LogP (AlogP): 6.13
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 28

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8996	89.96%
Caco-2	-	0.8347	83.47%
Blood Brain Barrier	+	0.5605	56.05%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7262	72.62%
OATP2B1 inhibitior	-	0.5642	56.42%
OATP1B1 inhibitior	+	0.8852	88.52%
OATP1B3 inhibitior	+	0.9307	93.07%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.6905	69.05%
P-glycoprotein inhibitior	+	0.6233	62.33%
P-glycoprotein substrate	-	0.6388	63.88%
CYP3A4 substrate	+	0.6430	64.30%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8577	85.77%
CYP3A4 inhibition	-	0.5913	59.13%
CYP2C9 inhibition	-	0.8369	83.69%
CYP2C19 inhibition	-	0.6159	61.59%
CYP2D6 inhibition	-	0.9217	92.17%
CYP1A2 inhibition	-	0.7561	75.61%
CYP2C8 inhibition	-	0.7656	76.56%
CYP inhibitory promiscuity	-	0.9367	93.67%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5706	57.06%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9009	90.09%
Skin irritation	+	0.5125	51.25%
Skin corrosion	-	0.9143	91.43%
Ames mutagenesis	-	0.7437	74.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4059	40.59%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	-	0.6145	61.45%
skin sensitisation	-	0.8361	83.61%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.7558	75.58%
Acute Oral Toxicity (c)	III	0.4037	40.37%
Estrogen receptor binding	+	0.7194	71.94%
Androgen receptor binding	+	0.5546	55.46%
Thyroid receptor binding	-	0.6524	65.24%
Glucocorticoid receptor binding	-	0.4865	48.65%
Aromatase binding	+	0.6033	60.33%
PPAR gamma	-	0.5682	56.82%
Honey bee toxicity	-	0.9364	93.64%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6673	66.73%
Fish aquatic toxicity	+	0.9719	97.19%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.11%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.74%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.56%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.25%	91.11%
CHEMBL230	P35354	Cyclooxygenase-2	92.67%	89.63%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	92.56%	92.86%
CHEMBL3401	O75469	Pregnane X receptor	90.47%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.16%	95.56%
CHEMBL3359	P21462	Formyl peptide receptor 1	89.02%	93.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.95%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.72%	99.17%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	87.49%	92.88%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	85.51%	85.94%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.91%	82.69%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.36%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.65%	95.89%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.49%	100.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.26%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.76%	97.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.63%	94.45%
CHEMBL5103	Q969S8	Histone deacetylase 10	82.46%	90.08%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	81.80%	97.29%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	81.39%	98.33%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	80.83%	92.08%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.23%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.18%	89.00%

Plants that contains it

• Annona salzmannii

Cross-Links

• PubChem: 101253930
• LOTUS: LTS0230691
• wikiData: Q105278220