[(3aS,4S,5R,6aR,9aR,9bR)-5-hydroxy-9-methyl-3,6-dimethylidene-2,7-dioxo-3a,4,5,6a,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] (E)-2-methylbut-2-enoate

Details

• Internal ID: 124aec0e-9f55-4740-b5da-71f84c2be15b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aS,4S,5R,6aR,9aR,9bR)-5-hydroxy-9-methyl-3,6-dimethylidene-2,7-dioxo-3a,4,5,6a,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] (E)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C2C(C3C(C(=C)C1O)C(=O)C=C3C)OC(=O)C2=C
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@H]1[C@@H]2[C@@H]([C@@H]3[C@H](C(=C)[C@H]1O)C(=O)C=C3C)OC(=O)C2=C
• InChI: InChI=1S/C20H22O6/c1-6-8(2)19(23)26-18-15-11(5)20(24)25-17(15)13-9(3)7-12(21)14(13)10(4)16(18)22/h6-7,13-18,22H,4-5H2,1-3H3/b8-6+/t13-,14+,15-,16+,17+,18-/m0/s1
• InChI Key: ZDPNAQGHTKJFQX-QZYQCRMVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂O₆
• Molecular Weight: 358.40 g/mol
• Exact Mass: 358.14163842 g/mol
• Topological Polar Surface Area (TPSA): 89.90 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.65
• H-Bond Acceptor: 6
• 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	+	0.9774	97.74%
Caco-2	-	0.5279	52.79%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5755	57.55%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8186	81.86%
OATP1B3 inhibitior	+	0.8998	89.98%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8009	80.09%
P-glycoprotein inhibitior	-	0.5949	59.49%
P-glycoprotein substrate	-	0.7343	73.43%
CYP3A4 substrate	+	0.5923	59.23%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9073	90.73%
CYP3A4 inhibition	-	0.7106	71.06%
CYP2C9 inhibition	-	0.9259	92.59%
CYP2C19 inhibition	-	0.7832	78.32%
CYP2D6 inhibition	-	0.9525	95.25%
CYP1A2 inhibition	-	0.7226	72.26%
CYP2C8 inhibition	-	0.6697	66.97%
CYP inhibitory promiscuity	-	0.8686	86.86%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9343	93.43%
Carcinogenicity (trinary)	Non-required	0.4209	42.09%
Eye corrosion	-	0.9092	90.92%
Eye irritation	-	0.8271	82.71%
Skin irritation	-	0.6497	64.97%
Skin corrosion	-	0.9388	93.88%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	+	0.7033	70.33%
skin sensitisation	-	0.6961	69.61%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.6604	66.04%
Acute Oral Toxicity (c)	IV	0.3536	35.36%
Estrogen receptor binding	+	0.7390	73.90%
Androgen receptor binding	+	0.5625	56.25%
Thyroid receptor binding	+	0.5887	58.87%
Glucocorticoid receptor binding	-	0.5119	51.19%
Aromatase binding	-	0.6128	61.28%
PPAR gamma	-	0.4847	48.47%
Honey bee toxicity	-	0.6647	66.47%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9496	94.96%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.62%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.33%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.98%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.39%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.95%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	88.60%	94.73%
CHEMBL2581	P07339	Cathepsin D	87.10%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.75%	86.33%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.84%	93.65%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.82%	94.00%

Plants that contains it

• Lasiolaena morii

Cross-Links

• PubChem: 163006151
• LOTUS: LTS0053639
• wikiData: Q105372544