Arteminolide A

Details

• Internal ID: 5b17c604-a162-41a4-aeab-70f327967244
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesterterpenoids
• IUPAC Name: [(1'R,2'R,3S,3aR,4S,5'S,9'S,9aS,9bR,10'S,11'S)-2'-hydroxy-2',6,9,11'-tetramethyl-6'-methylidene-2,7,7'-trioxospiro[4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-3,15'-8-oxatetracyclo[9.2.2.01,10.05,9]pentadec-12-ene]-4-yl] 3-methylbutanoate
• SMILES (Canonical): CC1=C2C(C3C(C(C1)OC(=O)CC(C)C)C4(CC56C=CC4(C5C7C(CCC6(C)O)C(=C)C(=O)O7)C)C(=O)O3)C(=CC2=O)C
• SMILES (Isomeric): CC1=C2[C@@H]([C@@H]3[C@@H]([C@H](C1)OC(=O)CC(C)C)[C@]4(C[C@@]56C=C[C@]4([C@@H]5[C@@H]7[C@@H](CC[C@@]6(C)O)C(=C)C(=O)O7)C)C(=O)O3)C(=CC2=O)C
• InChI: InChI=1S/C35H42O8/c1-16(2)12-23(37)41-22-14-18(4)24-21(36)13-17(3)25(24)28-26(22)35(31(39)43-28)15-34-11-10-32(35,6)29(34)27-20(8-9-33(34,7)40)19(5)30(38)42-27/h10-11,13,16,20,22,25-29,40H,5,8-9,12,14-15H2,1-4,6-7H3/t20-,22-,25-,26+,27-,28+,29-,32-,33+,34-,35+/m0/s1
• InChI Key: RAKYLPJLLBOHHN-PAIAVIFNSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₂O₈
• Molecular Weight: 590.70 g/mol
• Exact Mass: 590.28796829 g/mol
• Topological Polar Surface Area (TPSA): 116.00 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 4.56
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• [(1'R,2'R,3S,3Ar,4S,5'S,9'S,9aS,9bR,10'S,11'S)-2'-hydroxy-2',6,9,11'-tetramethyl-6'-methylidene-2,7,7'-trioxospiro[4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-3,15'-8-oxatetracyclo[9.2.2.01,10.05,9]pentadec-12-ene]-4-yl] 3-methylbutanoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9917	99.17%
Caco-2	-	0.7710	77.10%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7820	78.20%
OATP2B1 inhibitior	-	0.7206	72.06%
OATP1B1 inhibitior	+	0.8206	82.06%
OATP1B3 inhibitior	-	0.3603	36.03%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.8932	89.32%
P-glycoprotein inhibitior	+	0.8246	82.46%
P-glycoprotein substrate	+	0.7177	71.77%
CYP3A4 substrate	+	0.7252	72.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9124	91.24%
CYP3A4 inhibition	+	0.5776	57.76%
CYP2C9 inhibition	-	0.5517	55.17%
CYP2C19 inhibition	-	0.8451	84.51%
CYP2D6 inhibition	-	0.9553	95.53%
CYP1A2 inhibition	-	0.7123	71.23%
CYP2C8 inhibition	+	0.7380	73.80%
CYP inhibitory promiscuity	-	0.9285	92.85%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5775	57.75%
Eye corrosion	-	0.9862	98.62%
Eye irritation	-	0.9071	90.71%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9045	90.45%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7283	72.83%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.7500	75.00%
skin sensitisation	-	0.7780	77.80%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.5310	53.10%
Acute Oral Toxicity (c)	I	0.3094	30.94%
Estrogen receptor binding	+	0.8178	81.78%
Androgen receptor binding	+	0.7814	78.14%
Thyroid receptor binding	+	0.6269	62.69%
Glucocorticoid receptor binding	+	0.8084	80.84%
Aromatase binding	+	0.7508	75.08%
PPAR gamma	+	0.7243	72.43%
Honey bee toxicity	-	0.7086	70.86%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9956	99.56%

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	98.07%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.01%	85.14%
CHEMBL2581	P07339	Cathepsin D	96.98%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.92%	91.11%
CHEMBL2996	Q05655	Protein kinase C delta	94.45%	97.79%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.78%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	90.33%	90.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.79%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.39%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.46%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.74%	95.89%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	85.83%	90.93%
CHEMBL5028	O14672	ADAM10	85.41%	97.50%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.95%	96.47%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.67%	95.56%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.59%	95.71%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.35%	91.07%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.27%	97.14%
CHEMBL5600	P27448	Serine/threonine-protein kinase c-TAK1	82.51%	88.81%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.20%	95.89%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	81.66%	95.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.46%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.02%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.18%	94.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.09%	97.28%

Plants that contains it

• Artemisia argyi

Cross-Links

• PubChem: 15968984
• LOTUS: LTS0188423
• wikiData: Q104399551