[(3aR,4S,6aR,8S,9aR,9bR)-4-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-8-yl] 2-(hydroxymethyl)prop-2-enoate

Details

• Internal ID: 1fbb85d8-dcef-4659-9081-8d004ff2a637
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aR,4S,6aR,8S,9aR,9bR)-4-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-8-yl] 2-(hydroxymethyl)prop-2-enoate
• SMILES (Canonical): C=C1CC(C2C(C3C1CC(C3=C)OC(=O)C(=C)CO)OC(=O)C2=C)O
• SMILES (Isomeric): C=C1C[C@@H]([C@@H]2[C@@H]([C@@H]3[C@H]1C[C@@H](C3=C)OC(=O)C(=C)CO)OC(=O)C2=C)O
• InChI: InChI=1S/C19H22O6/c1-8-5-13(21)16-11(4)19(23)25-17(16)15-10(3)14(6-12(8)15)24-18(22)9(2)7-20/h12-17,20-21H,1-7H2/t12-,13-,14-,15-,16+,17+/m0/s1
• InChI Key: XPILSBOZTCGANP-NQLMQOPMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₆
• Molecular Weight: 346.40 g/mol
• Exact Mass: 346.14163842 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.06
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9776	97.76%
Caco-2	-	0.6620	66.20%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6079	60.79%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8791	87.91%
OATP1B3 inhibitior	+	0.9559	95.59%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9036	90.36%
P-glycoprotein inhibitior	-	0.7471	74.71%
P-glycoprotein substrate	-	0.5769	57.69%
CYP3A4 substrate	+	0.6269	62.69%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8228	82.28%
CYP3A4 inhibition	-	0.8308	83.08%
CYP2C9 inhibition	-	0.8816	88.16%
CYP2C19 inhibition	-	0.8290	82.90%
CYP2D6 inhibition	-	0.9145	91.45%
CYP1A2 inhibition	-	0.7904	79.04%
CYP2C8 inhibition	-	0.7963	79.63%
CYP inhibitory promiscuity	-	0.8741	87.41%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6613	66.13%
Eye corrosion	-	0.9416	94.16%
Eye irritation	-	0.5907	59.07%
Skin irritation	-	0.6794	67.94%
Skin corrosion	-	0.8874	88.74%
Ames mutagenesis	-	0.5824	58.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.6415	64.15%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.6524	65.24%
skin sensitisation	-	0.8020	80.20%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.6482	64.82%
Acute Oral Toxicity (c)	III	0.4692	46.92%
Estrogen receptor binding	+	0.6193	61.93%
Androgen receptor binding	+	0.6125	61.25%
Thyroid receptor binding	-	0.5660	56.60%
Glucocorticoid receptor binding	+	0.7403	74.03%
Aromatase binding	+	0.5579	55.79%
PPAR gamma	+	0.6305	63.05%
Honey bee toxicity	-	0.6090	60.90%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.8791	87.91%

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	94.38%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.78%	97.09%
CHEMBL2996	Q05655	Protein kinase C delta	86.78%	97.79%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.46%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.05%	99.23%
CHEMBL299	P17252	Protein kinase C alpha	82.11%	98.03%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.83%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.74%	95.56%

Plants that contains it

• Brachylaena perrieri
• Pseudostifftia kingii

Cross-Links

• PubChem: 15715078
• LOTUS: LTS0197642
• wikiData: Q105338394