[(3S,3aR,4S,6aR,8R,9aR,9bR)-8-hydroxy-3-methyl-6,9-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate

Details

• Internal ID: 81fc0641-1645-4206-ad4d-2b87ea29b9fb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3S,3aR,4S,6aR,8R,9aR,9bR)-8-hydroxy-3-methyl-6,9-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate
• SMILES (Canonical): CC1C2C(CC(=C)C3CC(C(=C)C3C2OC1=O)O)OC(=O)C(=C)CO
• SMILES (Isomeric): C[C@H]1[C@@H]2[C@H](CC(=C)[C@@H]3C[C@H](C(=C)[C@@H]3[C@H]2OC1=O)O)OC(=O)C(=C)CO
• InChI: InChI=1S/C19H24O6/c1-8-5-14(24-18(22)9(2)7-20)16-11(4)19(23)25-17(16)15-10(3)13(21)6-12(8)15/h11-17,20-21H,1-3,5-7H2,4H3/t11-,12-,13+,14-,15-,16+,17+/m0/s1
• InChI Key: CCBNOSMFTUQQLZ-OPCFMFSHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₄O₆
• Molecular Weight: 348.40 g/mol
• Exact Mass: 348.15728848 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.14
• 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	+	0.9763	97.63%
Caco-2	-	0.6394	63.94%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6235	62.35%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8798	87.98%
OATP1B3 inhibitior	+	0.9581	95.81%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8777	87.77%
P-glycoprotein inhibitior	-	0.8126	81.26%
P-glycoprotein substrate	+	0.5420	54.20%
CYP3A4 substrate	+	0.6368	63.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8838	88.38%
CYP3A4 inhibition	-	0.7464	74.64%
CYP2C9 inhibition	-	0.8500	85.00%
CYP2C19 inhibition	-	0.8357	83.57%
CYP2D6 inhibition	-	0.9338	93.38%
CYP1A2 inhibition	-	0.7393	73.93%
CYP2C8 inhibition	-	0.8664	86.64%
CYP inhibitory promiscuity	-	0.8415	84.15%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6163	61.63%
Eye corrosion	-	0.9631	96.31%
Eye irritation	-	0.7716	77.16%
Skin irritation	-	0.6645	66.45%
Skin corrosion	-	0.8984	89.84%
Ames mutagenesis	-	0.5208	52.08%
Human Ether-a-go-go-Related Gene inhibition	-	0.5383	53.83%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	-	0.7831	78.31%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.7319	73.19%
Acute Oral Toxicity (c)	III	0.4966	49.66%
Estrogen receptor binding	+	0.7240	72.40%
Androgen receptor binding	+	0.5914	59.14%
Thyroid receptor binding	+	0.6139	61.39%
Glucocorticoid receptor binding	+	0.6200	62.00%
Aromatase binding	+	0.5184	51.84%
PPAR gamma	+	0.5255	52.55%
Honey bee toxicity	-	0.7007	70.07%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.8915	89.15%

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	92.78%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.95%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.12%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	88.29%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.86%	99.17%
CHEMBL2581	P07339	Cathepsin D	84.52%	98.95%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.43%	93.04%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.12%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.10%	94.00%

Plants that contains it

• Saussurea laniceps

Cross-Links

• PubChem: 11360021
• LOTUS: LTS0113381
• wikiData: Q104953056