(8-hydroxy-3-methyl-6,9-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-4-yl) 2-methylprop-2-enoate

Details

• Internal ID: 4f1a17d5-e939-4e2e-b72f-15e596f639c7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (8-hydroxy-3-methyl-6,9-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-4-yl) 2-methylprop-2-enoate
• SMILES (Canonical): CC1C2C(CC(=C)C3CC(C(=C)C3C2OC1=O)O)OC(=O)C(=C)C
• SMILES (Isomeric): CC1C2C(CC(=C)C3CC(C(=C)C3C2OC1=O)O)OC(=O)C(=C)C
• InChI: InChI=1S/C19H24O5/c1-8(2)18(21)23-14-6-9(3)12-7-13(20)10(4)15(12)17-16(14)11(5)19(22)24-17/h11-17,20H,1,3-4,6-7H2,2,5H3
• InChI Key: IXOAQFFFKPCXLB-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₄O₅
• Molecular Weight: 332.40 g/mol
• Exact Mass: 332.16237386 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.17
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9824	98.24%
Caco-2	-	0.5539	55.39%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5923	59.23%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8877	88.77%
OATP1B3 inhibitior	+	0.9363	93.63%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8852	88.52%
P-glycoprotein inhibitior	-	0.8468	84.68%
P-glycoprotein substrate	-	0.5398	53.98%
CYP3A4 substrate	+	0.6348	63.48%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8823	88.23%
CYP3A4 inhibition	-	0.5718	57.18%
CYP2C9 inhibition	-	0.8958	89.58%
CYP2C19 inhibition	-	0.8439	84.39%
CYP2D6 inhibition	-	0.9489	94.89%
CYP1A2 inhibition	-	0.7734	77.34%
CYP2C8 inhibition	-	0.8685	86.85%
CYP inhibitory promiscuity	-	0.9115	91.15%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9425	94.25%
Carcinogenicity (trinary)	Non-required	0.5312	53.12%
Eye corrosion	-	0.9331	93.31%
Eye irritation	-	0.8035	80.35%
Skin irritation	-	0.6334	63.34%
Skin corrosion	-	0.9017	90.17%
Ames mutagenesis	+	0.5046	50.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.4641	46.41%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	+	0.7190	71.90%
skin sensitisation	-	0.6980	69.80%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.8255	82.55%
Acute Oral Toxicity (c)	II	0.4506	45.06%
Estrogen receptor binding	+	0.6937	69.37%
Androgen receptor binding	+	0.5798	57.98%
Thyroid receptor binding	-	0.5116	51.16%
Glucocorticoid receptor binding	-	0.4717	47.17%
Aromatase binding	-	0.5571	55.71%
PPAR gamma	-	0.5733	57.33%
Honey bee toxicity	-	0.5845	58.45%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9518	95.18%

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	93.60%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	91.61%	91.19%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.65%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.41%	97.09%
CHEMBL1951	P21397	Monoamine oxidase A	85.25%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.41%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.68%	89.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.12%	93.04%
CHEMBL2581	P07339	Cathepsin D	82.12%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.57%	95.56%

Plants that contains it

• Saussurea laniceps

Cross-Links

• PubChem: 14164981
• LOTUS: LTS0058446
• wikiData: Q105122316