[(1R,2S,3S,7R,8S,9S,13S)-9-acetyloxy-13-(hydroxymethyl)-6-methylidene-5-oxo-4,12-dioxatetracyclo[8.5.0.02,13.03,7]pentadec-10-en-8-yl] (2R)-2-methylbutanoate

Details

• Internal ID: 627385be-166a-4ca7-9ea7-d659a5e6d4ee
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(1R,2S,3S,7R,8S,9S,13S)-9-acetyloxy-13-(hydroxymethyl)-6-methylidene-5-oxo-4,12-dioxatetracyclo[8.5.0.02,13.03,7]pentadec-10-en-8-yl] (2R)-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1C2C(C3C4CCC3(OC=C4C1OC(=O)C)CO)OC(=O)C2=C
• SMILES (Isomeric): CC[C@@H](C)C(=O)O[C@H]1[C@H]2[C@@H]([C@@H]3[C@H]4CC[C@@]3(OC=C4[C@@H]1OC(=O)C)CO)OC(=O)C2=C
• InChI: InChI=1S/C22H28O8/c1-5-10(2)20(25)30-19-15-11(3)21(26)29-18(15)16-13-6-7-22(16,9-23)27-8-14(13)17(19)28-12(4)24/h8,10,13,15-19,23H,3,5-7,9H2,1-2,4H3/t10-,13+,15-,16+,17+,18+,19+,22-/m1/s1
• InChI Key: VBXKWULNKXQYJM-NMSPEYIOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₈
• Molecular Weight: 420.50 g/mol
• Exact Mass: 420.17841785 g/mol
• Topological Polar Surface Area (TPSA): 108.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 1.66
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9640	96.40%
Caco-2	-	0.6140	61.40%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8242	82.42%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7883	78.83%
OATP1B3 inhibitior	+	0.9004	90.04%
MATE1 inhibitior	-	0.8412	84.12%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.5141	51.41%
P-glycoprotein inhibitior	-	0.4922	49.22%
P-glycoprotein substrate	-	0.5094	50.94%
CYP3A4 substrate	+	0.6542	65.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8858	88.58%
CYP3A4 inhibition	-	0.5798	57.98%
CYP2C9 inhibition	-	0.7255	72.55%
CYP2C19 inhibition	-	0.8078	80.78%
CYP2D6 inhibition	-	0.9381	93.81%
CYP1A2 inhibition	-	0.7753	77.53%
CYP2C8 inhibition	+	0.4755	47.55%
CYP inhibitory promiscuity	-	0.8432	84.32%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5415	54.15%
Eye corrosion	-	0.9824	98.24%
Eye irritation	-	0.8976	89.76%
Skin irritation	-	0.5681	56.81%
Skin corrosion	-	0.9355	93.55%
Ames mutagenesis	-	0.7170	71.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5250	52.50%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.6427	64.27%
skin sensitisation	-	0.8836	88.36%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.5846	58.46%
Acute Oral Toxicity (c)	III	0.5089	50.89%
Estrogen receptor binding	+	0.7760	77.60%
Androgen receptor binding	+	0.7056	70.56%
Thyroid receptor binding	+	0.5165	51.65%
Glucocorticoid receptor binding	+	0.7289	72.89%
Aromatase binding	-	0.5502	55.02%
PPAR gamma	+	0.6041	60.41%
Honey bee toxicity	-	0.7173	71.73%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6550	65.50%
Fish aquatic toxicity	+	0.9746	97.46%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.54%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.33%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.86%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.68%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	93.71%	97.79%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.16%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.73%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.03%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.49%	89.00%
CHEMBL299	P17252	Protein kinase C alpha	86.18%	98.03%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.81%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.20%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.01%	86.33%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	83.22%	94.80%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.44%	95.89%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.04%	94.62%
CHEMBL4588	P22894	Matrix metalloproteinase 8	81.96%	94.66%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.73%	93.04%
CHEMBL226	P30542	Adenosine A1 receptor	81.14%	95.93%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.96%	93.03%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.92%	100.00%

Plants that contains it

• Acanthospermum hispidum

Cross-Links

• PubChem: 162797785
• LOTUS: LTS0037790
• wikiData: Q105283546