Tirotundin

Details

• Internal ID: 95833d10-8aba-46f2-93e9-f299793e8684
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(1R,2S,4R,8S,9R,11S)-1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.04,8]tetradecan-9-yl] 2-methylpropanoate
• SMILES (Canonical): CC1CC2C(C(CC3(CCC1(O3)O)C)OC(=O)C(C)C)C(=C)C(=O)O2
• SMILES (Isomeric): C[C@H]1C[C@@H]2[C@@H]([C@@H](C[C@@]3(CC[C@]1(O3)O)C)OC(=O)C(C)C)C(=C)C(=O)O2
• InChI: InChI=1S/C19H28O6/c1-10(2)16(20)24-14-9-18(5)6-7-19(22,25-18)11(3)8-13-15(14)12(4)17(21)23-13/h10-11,13-15,22H,4,6-9H2,1-3,5H3/t11-,13+,14+,15-,18-,19+/m0/s1
• InChI Key: VKWNXJLVNFOOOS-QNIDSSLUSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₈O₆
• Molecular Weight: 352.40 g/mol
• Exact Mass: 352.18858861 g/mol
• Topological Polar Surface Area (TPSA): 82.10 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.34
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• D06OBX
• CHEMBL464453
• GTPL8700
• MEGxp0_000078
• Propanoic acid, 2-methyl-, dodecahydro-9-hydroxy-6,10-dimethyl-3-methylene-2-oxo-6,9-epoxycyclodeca[b]furan-4-yl ester, [3aS-(3aR*,4S*,6R*,9S*,10R*,11aS*)]-
• BDBM50394803
• AKOS032948657
• Q27088999
• [(1R,2S,4R,8S,9R,11S)-1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.04,8]tetradecan-9-yl] 2-methylpropanoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9839	98.39%
Caco-2	+	0.6461	64.61%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7289	72.89%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9066	90.66%
OATP1B3 inhibitior	-	0.4040	40.40%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.6821	68.21%
BSEP inhibitior	-	0.9222	92.22%
P-glycoprotein inhibitior	-	0.7055	70.55%
P-glycoprotein substrate	-	0.7074	70.74%
CYP3A4 substrate	+	0.6496	64.96%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8858	88.58%
CYP3A4 inhibition	-	0.5851	58.51%
CYP2C9 inhibition	-	0.6832	68.32%
CYP2C19 inhibition	-	0.7910	79.10%
CYP2D6 inhibition	-	0.9543	95.43%
CYP1A2 inhibition	-	0.5334	53.34%
CYP2C8 inhibition	-	0.7422	74.22%
CYP inhibitory promiscuity	-	0.9507	95.07%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5461	54.61%
Eye corrosion	-	0.9836	98.36%
Eye irritation	-	0.8886	88.86%
Skin irritation	+	0.5385	53.85%
Skin corrosion	-	0.9007	90.07%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3854	38.54%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	+	0.6273	62.73%
skin sensitisation	-	0.7710	77.10%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.5762	57.62%
Acute Oral Toxicity (c)	II	0.3346	33.46%
Estrogen receptor binding	+	0.9213	92.13%
Androgen receptor binding	+	0.5589	55.89%
Thyroid receptor binding	+	0.6857	68.57%
Glucocorticoid receptor binding	+	0.7683	76.83%
Aromatase binding	+	0.6476	64.76%
PPAR gamma	+	0.7335	73.35%
Honey bee toxicity	-	0.7034	70.34%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9914	99.14%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL235	P37231	Peroxisome proliferator-activated receptor gamma	27000 nM	IC50	PMID: 22424975

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.63%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.96%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.88%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.29%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.55%	99.23%
CHEMBL299	P17252	Protein kinase C alpha	88.39%	98.03%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	88.28%	85.30%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.13%	85.14%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	88.09%	91.07%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.49%	95.56%
CHEMBL2996	Q05655	Protein kinase C delta	86.20%	97.79%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.31%	95.50%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	85.07%	95.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.80%	97.09%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	84.73%	94.08%
CHEMBL340	P08684	Cytochrome P450 3A4	84.67%	91.19%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.61%	82.69%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.00%	86.33%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.84%	95.71%
CHEMBL221	P23219	Cyclooxygenase-1	82.86%	90.17%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.52%	97.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.47%	96.77%

Plants that contains it

• Helianthus niveus
• Tithonia diversifolia
• Tithonia rotundifolia

Cross-Links

• PubChem: 9975297
• NPASS: NPC162071
• ChEMBL: CHEMBL464453
• LOTUS: LTS0115599
• wikiData: Q27088999