(3aR,4S,6aR,9aR,9bR)-4-hydroxy-3,6,9-trimethylidene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one

Details

• Internal ID: 2e2bda42-cb59-49d1-858d-cf4f66266a2f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aR,4S,6aR,9aR,9bR)-4-hydroxy-3,6,9-trimethylidene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one
• SMILES (Canonical): C=C1CCC2C1C3C(C(CC2=C)O)C(=C)C(=O)O3
• SMILES (Isomeric): C=C1CC[C@@H]2[C@H]1[C@@H]3[C@@H]([C@H](CC2=C)O)C(=C)C(=O)O3
• InChI: InChI=1S/C15H18O3/c1-7-4-5-10-8(2)6-11(16)13-9(3)15(17)18-14(13)12(7)10/h10-14,16H,1-6H2/t10-,11-,12-,13+,14+/m0/s1
• InChI Key: VNKCRRIDZAQRBP-QSLWVIQJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.30 g/mol
• Exact Mass: 246.125594432 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.99
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9941	99.41%
Caco-2	+	0.5297	52.97%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.7286	72.86%
Subcellular localzation	Mitochondria	0.4890	48.90%
OATP2B1 inhibitior	-	0.8564	85.64%
OATP1B1 inhibitior	+	0.9083	90.83%
OATP1B3 inhibitior	+	0.9541	95.41%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.9528	95.28%
P-glycoprotein inhibitior	-	0.9206	92.06%
P-glycoprotein substrate	-	0.9047	90.47%
CYP3A4 substrate	+	0.5213	52.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7973	79.73%
CYP3A4 inhibition	-	0.8287	82.87%
CYP2C9 inhibition	-	0.9474	94.74%
CYP2C19 inhibition	-	0.8364	83.64%
CYP2D6 inhibition	-	0.9383	93.83%
CYP1A2 inhibition	-	0.7164	71.64%
CYP2C8 inhibition	-	0.9401	94.01%
CYP inhibitory promiscuity	-	0.9533	95.33%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5962	59.62%
Eye corrosion	-	0.7627	76.27%
Eye irritation	+	0.7970	79.70%
Skin irritation	-	0.6287	62.87%
Skin corrosion	-	0.9380	93.80%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7697	76.97%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.8408	84.08%
skin sensitisation	-	0.6826	68.26%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.4836	48.36%
Acute Oral Toxicity (c)	III	0.4790	47.90%
Estrogen receptor binding	+	0.5369	53.69%
Androgen receptor binding	+	0.5317	53.17%
Thyroid receptor binding	-	0.5413	54.13%
Glucocorticoid receptor binding	+	0.7001	70.01%
Aromatase binding	-	0.7971	79.71%
PPAR gamma	-	0.6687	66.87%
Honey bee toxicity	-	0.7831	78.31%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.8700	87.00%

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	93.08%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.70%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.72%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.58%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.47%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.21%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.88%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.14%	89.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.84%	93.03%

Plants that contains it

• Cheirolophus canariensis

Cross-Links

• PubChem: 101675253
• LOTUS: LTS0138966
• wikiData: Q105289680