[(3aR,4S,6aR,8S,9S,9aS,9bS)-9-(chloromethyl)-4,9-dihydroxy-3,6-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-8-yl] benzoate

Details

• Internal ID: 7d0c0890-5643-4ac5-af2c-801ca73b2e1e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aR,4S,6aR,8S,9S,9aS,9bS)-9-(chloromethyl)-4,9-dihydroxy-3,6-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-8-yl] benzoate
• InChI: InChI=1S/C22H23ClO6/c1-11-8-15(24)17-12(2)20(25)29-19(17)18-14(11)9-16(22(18,27)10-23)28-21(26)13-6-4-3-5-7-13/h3-7,14-19,24,27H,1-2,8-10H2/t14-,15-,16-,17+,18-,19-,22+/m0/s1
• InChI Key: FKRRWLGLGLGHLD-BZKPKAPTSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₃ClO₆
• Molecular Weight: 418.90 g/mol
• Exact Mass: 418.1183161 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.24
• 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	+	0.9748	97.48%
Caco-2	-	0.7253	72.53%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7221	72.21%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8688	86.88%
OATP1B3 inhibitior	+	0.9391	93.91%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8529	85.29%
P-glycoprotein inhibitior	-	0.5744	57.44%
P-glycoprotein substrate	-	0.6070	60.70%
CYP3A4 substrate	+	0.6625	66.25%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8277	82.77%
CYP3A4 inhibition	-	0.6528	65.28%
CYP2C9 inhibition	-	0.7777	77.77%
CYP2C19 inhibition	-	0.6884	68.84%
CYP2D6 inhibition	-	0.8955	89.55%
CYP1A2 inhibition	-	0.8027	80.27%
CYP2C8 inhibition	+	0.5566	55.66%
CYP inhibitory promiscuity	-	0.8683	86.83%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8544	85.44%
Carcinogenicity (trinary)	Non-required	0.4810	48.10%
Eye corrosion	-	0.9763	97.63%
Eye irritation	-	0.9239	92.39%
Skin irritation	-	0.6943	69.43%
Skin corrosion	-	0.9195	91.95%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6484	64.84%
Micronuclear	-	0.6441	64.41%
Hepatotoxicity	+	0.6288	62.88%
skin sensitisation	-	0.7541	75.41%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.7228	72.28%
Acute Oral Toxicity (c)	III	0.4671	46.71%
Estrogen receptor binding	+	0.6482	64.82%
Androgen receptor binding	+	0.5796	57.96%
Thyroid receptor binding	-	0.5374	53.74%
Glucocorticoid receptor binding	+	0.7289	72.89%
Aromatase binding	+	0.5927	59.27%
PPAR gamma	+	0.6480	64.80%
Honey bee toxicity	-	0.7023	70.23%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9938	99.38%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	97.38%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.19%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.71%	91.11%
CHEMBL2581	P07339	Cathepsin D	87.39%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.48%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.17%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.79%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.58%	99.23%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.36%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.31%	95.89%
CHEMBL5957	P21589	5'-nucleotidase	81.20%	97.78%
CHEMBL5028	O14672	ADAM10	81.10%	97.50%

Plants that contains it

• Centaurea scoparia

Cross-Links

• PubChem: 162916868
• LOTUS: LTS0005311
• wikiData: Q104996759