(3R,3aS,6R,6aS,10S,10aS)-10-hydroxy-3,6-dimethyl-9-methylidene-3a,4,5,6,6a,7,8,10-octahydro-3H-benzo[h][1]benzofuran-2-one

Details

• Internal ID: 8d4bd9d5-d9ec-483c-998e-47eaf449e14b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Cadinanolides
• IUPAC Name: (3R,3aS,6R,6aS,10S,10aS)-10-hydroxy-3,6-dimethyl-9-methylidene-3a,4,5,6,6a,7,8,10-octahydro-3H-benzo[h][1]benzofuran-2-one
• SMILES (Canonical): CC1CCC2C(C(=O)OC23C1CCC(=C)C3O)C
• SMILES (Isomeric): C[C@@H]1CC[C@H]2[C@H](C(=O)O[C@@]23[C@H]1CCC(=C)[C@@H]3O)C
• InChI: InChI=1S/C15H22O3/c1-8-4-7-12-10(3)14(17)18-15(12)11(8)6-5-9(2)13(15)16/h8,10-13,16H,2,4-7H2,1,3H3/t8-,10-,11+,12+,13+,15+/m1/s1
• InChI Key: PJCCSJGLHBNKPR-MBICNOSFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.33 g/mol
• Exact Mass: 250.15689456 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.29
• 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	+	0.9940	99.40%
Caco-2	+	0.7903	79.03%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6999	69.99%
OATP2B1 inhibitior	-	0.8534	85.34%
OATP1B1 inhibitior	+	0.9148	91.48%
OATP1B3 inhibitior	+	0.8787	87.87%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.6000	60.00%
BSEP inhibitior	-	0.9386	93.86%
P-glycoprotein inhibitior	-	0.9375	93.75%
P-glycoprotein substrate	-	0.9118	91.18%
CYP3A4 substrate	+	0.6425	64.25%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8240	82.40%
CYP3A4 inhibition	+	0.5156	51.56%
CYP2C9 inhibition	-	0.8459	84.59%
CYP2C19 inhibition	-	0.6371	63.71%
CYP2D6 inhibition	-	0.9125	91.25%
CYP1A2 inhibition	+	0.6319	63.19%
CYP2C8 inhibition	-	0.8243	82.43%
CYP inhibitory promiscuity	-	0.7875	78.75%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5203	52.03%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.7754	77.54%
Skin irritation	+	0.5244	52.44%
Skin corrosion	-	0.9143	91.43%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6851	68.51%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.7125	71.25%
skin sensitisation	-	0.6472	64.72%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.5098	50.98%
Estrogen receptor binding	+	0.5997	59.97%
Androgen receptor binding	+	0.7105	71.05%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.5467	54.67%
Aromatase binding	-	0.7900	79.00%
PPAR gamma	-	0.7585	75.85%
Honey bee toxicity	-	0.8037	80.37%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	93.01%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.67%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.11%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.27%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.00%	97.25%
CHEMBL2581	P07339	Cathepsin D	86.05%	98.95%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	85.54%	96.38%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.40%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.49%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.68%	94.45%
CHEMBL1871	P10275	Androgen Receptor	80.53%	96.43%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.22%	89.00%

Plants that contains it

• Artemisia annua

Cross-Links

• PubChem: 15377688
• LOTUS: LTS0011993
• wikiData: Q105209877