Artanomalide B

Details

• Internal ID: 824f5adb-eb82-43f0-9c67-edda50648b78
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (1R,2S,5S,9S,10S,11R,12S,13R)-12-chloro-2,11-dihydroxy-2,11-dimethyl-6-methylidene-8,14-dioxatetracyclo[8.4.0.01,13.05,9]tetradecan-7-one
• SMILES (Canonical): CC1(CCC2C(C3C14C(O4)C(C3(C)O)Cl)OC(=O)C2=C)O
• SMILES (Isomeric): C[C@@]1(CC[C@@H]2[C@@H]([C@@H]3[C@@]14[C@@H](O4)[C@@H]([C@]3(C)O)Cl)OC(=O)C2=C)O
• InChI: InChI=1S/C15H19ClO5/c1-6-7-4-5-13(2,18)15-9(8(7)20-12(6)17)14(3,19)10(16)11(15)21-15/h7-11,18-19H,1,4-5H2,2-3H3/t7-,8-,9-,10-,11-,13-,14+,15+/m0/s1
• InChI Key: LSJACVRYYGZXIP-CJGKHJOQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₉ClO₅
• Molecular Weight: 314.76 g/mol
• Exact Mass: 314.0921014 g/mol
• Topological Polar Surface Area (TPSA): 79.30 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.75
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• CHEMBL1087258
• 8alpha-Chloro-6alpha,9alpha-dihydroxy-3-methylene-6,9-dimethyl-3abeta,4,5,7,8,9,9abeta,9balpha-octahydro-6H-6abeta,7beta-epoxyazuleno[4,5-b]furan-2(3H)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9852	98.52%
Caco-2	-	0.5262	52.62%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.5714	57.14%
OATP2B1 inhibitior	-	0.8534	85.34%
OATP1B1 inhibitior	+	0.8512	85.12%
OATP1B3 inhibitior	+	0.9389	93.89%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9715	97.15%
P-glycoprotein inhibitior	-	0.8587	85.87%
P-glycoprotein substrate	-	0.8157	81.57%
CYP3A4 substrate	+	0.6481	64.81%
CYP2C9 substrate	-	0.8071	80.71%
CYP2D6 substrate	-	0.8526	85.26%
CYP3A4 inhibition	-	0.7659	76.59%
CYP2C9 inhibition	-	0.8207	82.07%
CYP2C19 inhibition	-	0.8340	83.40%
CYP2D6 inhibition	-	0.8885	88.85%
CYP1A2 inhibition	-	0.7778	77.78%
CYP2C8 inhibition	-	0.6408	64.08%
CYP inhibitory promiscuity	-	0.9241	92.41%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8482	84.82%
Carcinogenicity (trinary)	Non-required	0.4327	43.27%
Eye corrosion	-	0.9808	98.08%
Eye irritation	-	0.9640	96.40%
Skin irritation	-	0.6352	63.52%
Skin corrosion	-	0.8539	85.39%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5609	56.09%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.8678	86.78%
skin sensitisation	-	0.7617	76.17%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.7909	79.09%
Acute Oral Toxicity (c)	III	0.4396	43.96%
Estrogen receptor binding	+	0.7888	78.88%
Androgen receptor binding	+	0.6786	67.86%
Thyroid receptor binding	+	0.6916	69.16%
Glucocorticoid receptor binding	+	0.6124	61.24%
Aromatase binding	+	0.5940	59.40%
PPAR gamma	+	0.5886	58.86%
Honey bee toxicity	-	0.6789	67.89%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	+	0.9568	95.68%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.92%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.82%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.76%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.66%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.09%	97.09%
CHEMBL259	P32245	Melanocortin receptor 4	85.59%	95.38%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.50%	96.61%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.36%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.60%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	80.01%	90.17%

Plants that contains it

• Artemisia anomala

Cross-Links

• PubChem: 44627810
• NPASS: NPC115352
• LOTUS: LTS0201382
• wikiData: Q105156565