(3S,5S)-5-[7-[(2R,5R)-5-[(1S,4R)-1,4-dihydroxy-4-[(2R,5R)-5-[(1R)-1-hydroxyundecyl]oxolan-2-yl]butyl]oxolan-2-yl]heptyl]-3-(2-oxopropyl)oxolan-2-one

Details

• Internal ID: 7b4e4f86-bd6b-4f4a-ac38-97ba7ff9e888
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty alcohols > Annonaceous acetogenins
• IUPAC Name: (3S,5S)-5-[7-[(2R,5R)-5-[(1S,4R)-1,4-dihydroxy-4-[(2R,5R)-5-[(1R)-1-hydroxyundecyl]oxolan-2-yl]butyl]oxolan-2-yl]heptyl]-3-(2-oxopropyl)oxolan-2-one
• SMILES (Canonical): CCCCCCCCCCC(C1CCC(O1)C(CCC(C2CCC(O2)CCCCCCCC3CC(C(=O)O3)CC(=O)C)O)O)O
• SMILES (Isomeric): CCCCCCCCCC[C@H]([C@H]1CC[C@@H](O1)[C@@H](CC[C@@H]([C@H]2CC[C@H](O2)CCCCCCC[C@H]3C[C@H](C(=O)O3)CC(=O)C)O)O)O
• InChI: InChI=1S/C37H66O8/c1-3-4-5-6-7-8-12-15-18-31(39)35-23-24-36(45-35)33(41)21-20-32(40)34-22-19-29(43-34)16-13-10-9-11-14-17-30-26-28(25-27(2)38)37(42)44-30/h28-36,39-41H,3-26H2,1-2H3/t28-,29-,30+,31-,32+,33-,34-,35-,36-/m1/s1
• InChI Key: WAZNHZWSJGMXPS-VNTGYUCWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₆₆O₈
• Molecular Weight: 638.90 g/mol
• Exact Mass: 638.47576906 g/mol
• Topological Polar Surface Area (TPSA): 123.00 Ų
• XlogP: 7.80
• Atomic LogP (AlogP): 7.12
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 25

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8993	89.93%
Caco-2	-	0.8289	82.89%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8018	80.18%
OATP2B1 inhibitior	-	0.5621	56.21%
OATP1B1 inhibitior	+	0.8957	89.57%
OATP1B3 inhibitior	+	0.8971	89.71%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7467	74.67%
P-glycoprotein inhibitior	+	0.6473	64.73%
P-glycoprotein substrate	+	0.5610	56.10%
CYP3A4 substrate	+	0.6238	62.38%
CYP2C9 substrate	-	0.7891	78.91%
CYP2D6 substrate	-	0.8505	85.05%
CYP3A4 inhibition	-	0.6749	67.49%
CYP2C9 inhibition	-	0.9079	90.79%
CYP2C19 inhibition	-	0.8422	84.22%
CYP2D6 inhibition	-	0.9359	93.59%
CYP1A2 inhibition	-	0.8627	86.27%
CYP2C8 inhibition	-	0.7357	73.57%
CYP inhibitory promiscuity	-	0.9740	97.40%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7029	70.29%
Eye corrosion	-	0.9847	98.47%
Eye irritation	-	0.8494	84.94%
Skin irritation	-	0.6156	61.56%
Skin corrosion	-	0.8946	89.46%
Ames mutagenesis	-	0.8037	80.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.3995	39.95%
Micronuclear	-	0.9500	95.00%
Hepatotoxicity	+	0.5301	53.01%
skin sensitisation	-	0.9009	90.09%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.5202	52.02%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.7790	77.90%
Acute Oral Toxicity (c)	III	0.5904	59.04%
Estrogen receptor binding	+	0.7441	74.41%
Androgen receptor binding	+	0.6447	64.47%
Thyroid receptor binding	-	0.6360	63.60%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.5921	59.21%
PPAR gamma	+	0.5541	55.41%
Honey bee toxicity	-	0.9334	93.34%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.6128	61.28%
Fish aquatic toxicity	+	0.9400	94.00%

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	97.12%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.94%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.16%	97.25%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.71%	99.17%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	91.57%	97.29%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.25%	91.11%
CHEMBL230	P35354	Cyclooxygenase-2	91.22%	89.63%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.52%	97.09%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	89.63%	100.00%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	87.85%	92.86%
CHEMBL4462	Q8IXJ6	NAD-dependent deacetylase sirtuin 2	86.94%	90.24%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.43%	93.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.39%	89.00%
CHEMBL5255	O00206	Toll-like receptor 4	85.07%	92.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.88%	95.56%
CHEMBL4588	P22894	Matrix metalloproteinase 8	84.29%	94.66%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	84.19%	85.94%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.61%	94.33%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	83.37%	92.08%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.30%	99.23%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.80%	95.50%
CHEMBL340	P08684	Cytochrome P450 3A4	82.30%	91.19%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	82.09%	92.88%
CHEMBL3401	O75469	Pregnane X receptor	81.92%	94.73%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.67%	95.89%
CHEMBL5103	Q969S8	Histone deacetylase 10	81.52%	90.08%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.41%	90.71%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.87%	100.00%
CHEMBL1944495	P28065	Proteasome subunit beta type-9	80.34%	97.50%

Plants that contains it

• Annona bullata

Cross-Links

• PubChem: 162920008
• LOTUS: LTS0106560
• wikiData: Q105300557