[(3aR,4R,6R,6aR,9aR,9bR)-6-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] (3R)-3-hydroxy-2-methylidenebutanoate

Details

• Internal ID: 133e8dcd-633c-4e43-911c-636701fd5dc2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aR,4R,6R,6aR,9aR,9bR)-6-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] (3R)-3-hydroxy-2-methylidenebutanoate
• SMILES (Canonical): CC1=CCC2C1C3C(C(CC2(C)O)OC(=O)C(=C)C(C)O)C(=C)C(=O)O3
• SMILES (Isomeric): CC1=CC[C@@H]2[C@H]1[C@@H]3[C@@H]([C@@H](C[C@@]2(C)O)OC(=O)C(=C)[C@@H](C)O)C(=C)C(=O)O3
• InChI: InChI=1S/C20H26O6/c1-9-6-7-13-15(9)17-16(11(3)19(23)26-17)14(8-20(13,5)24)25-18(22)10(2)12(4)21/h6,12-17,21,24H,2-3,7-8H2,1,4-5H3/t12-,13-,14-,15+,16-,17-,20-/m1/s1
• InChI Key: QMBUSVJDHSRQQH-HLVUYRRWSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₆
• Molecular Weight: 362.40 g/mol
• Exact Mass: 362.17293854 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.67
• 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	+	0.9873	98.73%
Caco-2	-	0.5907	59.07%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5428	54.28%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9075	90.75%
OATP1B3 inhibitior	+	0.9068	90.68%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9758	97.58%
P-glycoprotein inhibitior	-	0.6641	66.41%
P-glycoprotein substrate	-	0.6003	60.03%
CYP3A4 substrate	+	0.6528	65.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8583	85.83%
CYP3A4 inhibition	-	0.5288	52.88%
CYP2C9 inhibition	-	0.7999	79.99%
CYP2C19 inhibition	-	0.8600	86.00%
CYP2D6 inhibition	-	0.9603	96.03%
CYP1A2 inhibition	-	0.6526	65.26%
CYP2C8 inhibition	-	0.6916	69.16%
CYP inhibitory promiscuity	-	0.9522	95.22%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5206	52.06%
Eye corrosion	-	0.9792	97.92%
Eye irritation	-	0.8749	87.49%
Skin irritation	-	0.5550	55.50%
Skin corrosion	-	0.9001	90.01%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4085	40.85%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.6816	68.16%
skin sensitisation	-	0.7325	73.25%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.5350	53.50%
Acute Oral Toxicity (c)	II	0.4223	42.23%
Estrogen receptor binding	+	0.6859	68.59%
Androgen receptor binding	+	0.6572	65.72%
Thyroid receptor binding	+	0.5929	59.29%
Glucocorticoid receptor binding	+	0.6596	65.96%
Aromatase binding	-	0.5275	52.75%
PPAR gamma	+	0.5673	56.73%
Honey bee toxicity	-	0.6278	62.78%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5650	56.50%
Fish aquatic toxicity	+	0.9882	98.82%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.75%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	96.49%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.04%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.06%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.76%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.01%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.26%	85.14%
CHEMBL2581	P07339	Cathepsin D	87.85%	98.95%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	87.76%	96.47%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.13%	91.07%
CHEMBL230	P35354	Cyclooxygenase-2	86.62%	89.63%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.18%	86.33%
CHEMBL4040	P28482	MAP kinase ERK2	85.18%	83.82%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.76%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.47%	97.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.77%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.61%	96.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.03%	93.03%
CHEMBL2996	Q05655	Protein kinase C delta	82.44%	97.79%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.10%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	81.72%	94.73%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	80.01%	94.08%

Plants that contains it

• Helianthus maximiliani

Cross-Links

• PubChem: 163013466
• LOTUS: LTS0095311
• wikiData: Q105223904