Trichilin A

Details

• Internal ID: 3f3456ed-a7f9-46d3-a729-e9534674fdb9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(1S,2R,4S,5R,6S,8R,10S,11S,12R,14R,15R,19R,20R,21S)-20,21-diacetyloxy-6-(furan-3-yl)-4,12,19-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.01,14.02,11.05,10.08,10]henicosan-16-yl] (2R)-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1C2(C3CC(C4(C(C3(CO1)C(C(C2OC(=O)C)OC(=O)C)O)C(=O)C(C5(C46C(O6)CC5C7=COC=C7)C)O)C)O)C
• SMILES (Isomeric): CC[C@@H](C)C(=O)OC1[C@@]2([C@@H]3C[C@H]([C@@]4([C@@H]([C@@]3(CO1)[C@H]([C@H]([C@H]2OC(=O)C)OC(=O)C)O)C(=O)[C@H]([C@@]5([C@]46[C@H](O6)C[C@H]5C7=COC=C7)C)O)C)O)C
• InChI: InChI=1S/C35H46O13/c1-8-15(2)29(42)47-30-31(5)20-12-21(38)33(7)25(34(20,14-44-30)27(41)24(45-16(3)36)28(31)46-17(4)37)23(39)26(40)32(6)19(18-9-10-43-13-18)11-22-35(32,33)48-22/h9-10,13,15,19-22,24-28,30,38,40-41H,8,11-12,14H2,1-7H3/t15-,19+,20+,21-,22-,24-,25+,26-,27+,28-,30?,31-,32-,33-,34+,35-/m1/s1
• InChI Key: AYBKFVIPPCLFDH-KPZLONJUSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₆O₁₃
• Molecular Weight: 674.70 g/mol
• Exact Mass: 674.29384152 g/mol
• Topological Polar Surface Area (TPSA): 192.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.03
• H-Bond Acceptor: 13
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• C08786
• 77182-69-5
• C35-H46-O13
• CHEBI:9681
• DTXSID30998441
• [(1S,2R,4S,5R,6S,8R,10S,11S,12R,14R,15R,19R,20R,21S)-20,21-diacetyloxy-6-(furan-3-yl)-4,12,19-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.01,14.02,11.05,10.08,10]henicosan-16-yl] (2R)-2-methylbutanoate
• 2,3-bis(acetyloxy)-9-(furan-3-yl)-1,6,10-trihydroxy-4,6a,9a-trimethyl-11-oxotetradecahydro-1H-4,11b-(methanooxymethano)naphtho[1',2':6,7]indeno[1,7a-b]oxiren-14-yl 2-methylbutanoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9702	97.02%
Caco-2	-	0.8295	82.95%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7248	72.48%
OATP2B1 inhibitior	-	0.8601	86.01%
OATP1B1 inhibitior	+	0.6953	69.53%
OATP1B3 inhibitior	+	0.8252	82.52%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9498	94.98%
P-glycoprotein inhibitior	+	0.7762	77.62%
P-glycoprotein substrate	+	0.6669	66.69%
CYP3A4 substrate	+	0.7051	70.51%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8322	83.22%
CYP3A4 inhibition	+	0.6602	66.02%
CYP2C9 inhibition	-	0.7598	75.98%
CYP2C19 inhibition	-	0.8361	83.61%
CYP2D6 inhibition	-	0.9481	94.81%
CYP1A2 inhibition	-	0.8754	87.54%
CYP2C8 inhibition	+	0.7070	70.70%
CYP inhibitory promiscuity	-	0.7882	78.82%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5334	53.34%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9096	90.96%
Skin irritation	-	0.7064	70.64%
Skin corrosion	-	0.9388	93.88%
Ames mutagenesis	-	0.5455	54.55%
Human Ether-a-go-go-Related Gene inhibition	-	0.4005	40.05%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.5876	58.76%
skin sensitisation	-	0.8882	88.82%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.5492	54.92%
Acute Oral Toxicity (c)	I	0.4393	43.93%
Estrogen receptor binding	+	0.8078	80.78%
Androgen receptor binding	+	0.7530	75.30%
Thyroid receptor binding	+	0.5430	54.30%
Glucocorticoid receptor binding	+	0.7737	77.37%
Aromatase binding	+	0.6918	69.18%
PPAR gamma	+	0.7840	78.40%
Honey bee toxicity	-	0.7144	71.44%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9821	98.21%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.64%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.87%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	97.73%	90.17%
CHEMBL2581	P07339	Cathepsin D	97.58%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.40%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.28%	97.25%
CHEMBL4040	P28482	MAP kinase ERK2	93.21%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.15%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.99%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.02%	89.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	88.91%	97.28%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.83%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.83%	85.14%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	86.29%	95.71%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.36%	96.77%
CHEMBL2996	Q05655	Protein kinase C delta	85.22%	97.79%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.66%	94.00%
CHEMBL340	P08684	Cytochrome P450 3A4	84.45%	91.19%
CHEMBL3401	O75469	Pregnane X receptor	84.03%	94.73%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.06%	92.62%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	81.88%	98.75%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.72%	82.69%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.70%	96.47%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.01%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.46%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.44%	93.00%

Plants that contains it

• Melia azedarach
• Trichilia emetica

Cross-Links

• PubChem: 5462417
• NPASS: NPC71905
• LOTUS: LTS0227048
• wikiData: Q82991026