[(3aR,4S,6aR,8S,9aR,9bR)-4-[2-(hydroxymethyl)prop-2-enoyloxy]-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: 2d6c053a-4339-4eaa-9677-9c7cc5f7d3fe
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aR,4S,6aR,8S,9aR,9bR)-4-[2-(hydroxymethyl)prop-2-enoyloxy]-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)OC(=O)C(=C)CO
• 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)OC(=O)C(=C)CO
• InChI: InChI=1S/C23H26O8/c1-10-6-17(30-22(27)12(3)9-25)19-14(5)23(28)31-20(19)18-13(4)16(7-15(10)18)29-21(26)11(2)8-24/h15-20,24-25H,1-9H2/t15-,16-,17-,18-,19+,20+/m0/s1
• InChI Key: BDBLHYZLGQCCHF-GFLQDLJJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₆O₈
• Molecular Weight: 430.40 g/mol
• Exact Mass: 430.16276778 g/mol
• Topological Polar Surface Area (TPSA): 119.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.16
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• ACon0_001483
• ACon1_000024
• NCGC00168866-01
• BRD-K60750751-001-01-1

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9569	95.69%
Caco-2	-	0.7914	79.14%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6596	65.96%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8968	89.68%
OATP1B3 inhibitior	+	0.9531	95.31%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7550	75.50%
P-glycoprotein inhibitior	-	0.5100	51.00%
P-glycoprotein substrate	-	0.6017	60.17%
CYP3A4 substrate	+	0.6252	62.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8268	82.68%
CYP3A4 inhibition	-	0.8570	85.70%
CYP2C9 inhibition	-	0.8615	86.15%
CYP2C19 inhibition	-	0.7446	74.46%
CYP2D6 inhibition	-	0.9145	91.45%
CYP1A2 inhibition	-	0.7779	77.79%
CYP2C8 inhibition	-	0.7325	73.25%
CYP inhibitory promiscuity	-	0.8222	82.22%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9243	92.43%
Carcinogenicity (trinary)	Non-required	0.6163	61.63%
Eye corrosion	-	0.9382	93.82%
Eye irritation	-	0.7570	75.70%
Skin irritation	-	0.6838	68.38%
Skin corrosion	-	0.8710	87.10%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4233	42.33%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.7706	77.06%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.7066	70.66%
Acute Oral Toxicity (c)	III	0.4648	46.48%
Estrogen receptor binding	+	0.6492	64.92%
Androgen receptor binding	+	0.6154	61.54%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6664	66.64%
Aromatase binding	+	0.5937	59.37%
PPAR gamma	+	0.6993	69.93%
Honey bee toxicity	-	0.6063	60.63%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9036	90.36%

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	93.21%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.57%	97.09%
CHEMBL2996	Q05655	Protein kinase C delta	90.07%	97.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.00%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.67%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	81.52%	91.19%
CHEMBL299	P17252	Protein kinase C alpha	80.46%	98.03%

Plants that contains it

• Brachylaena perrieri

Cross-Links

• PubChem: 15715079
• LOTUS: LTS0166212
• wikiData: Q104923775