(1S,3aS,7S,9S,9aS,9bR)-3a,7-dihydroxy-1,9,9a-trimethyl-4,5,7,8,9,9b-hexahydro-1H-benzo[e][1]benzofuran-2-one

Details

• Internal ID: 3fa63934-6dff-422d-b45d-b04568376e9e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (1S,3aS,7S,9S,9aS,9bR)-3a,7-dihydroxy-1,9,9a-trimethyl-4,5,7,8,9,9b-hexahydro-1H-benzo[e][1]benzofuran-2-one
• SMILES (Canonical): CC1CC(C=C2C1(C3C(C(=O)OC3(CC2)O)C)C)O
• SMILES (Isomeric): C[C@H]1C[C@@H](C=C2[C@@]1([C@H]3[C@@H](C(=O)O[C@]3(CC2)O)C)C)O
• InChI: InChI=1S/C15H22O4/c1-8-6-11(16)7-10-4-5-15(18)12(14(8,10)3)9(2)13(17)19-15/h7-9,11-12,16,18H,4-6H2,1-3H3/t8-,9-,11-,12+,14+,15-/m0/s1
• InChI Key: JKTAMRQCOYUPQI-FGVNRAKHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.61
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9936	99.36%
Caco-2	+	0.6242	62.42%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7049	70.49%
OATP2B1 inhibitior	-	0.8539	85.39%
OATP1B1 inhibitior	+	0.9072	90.72%
OATP1B3 inhibitior	+	0.9213	92.13%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5571	55.71%
BSEP inhibitior	-	0.8492	84.92%
P-glycoprotein inhibitior	-	0.9095	90.95%
P-glycoprotein substrate	-	0.7709	77.09%
CYP3A4 substrate	+	0.6358	63.58%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8507	85.07%
CYP3A4 inhibition	-	0.7114	71.14%
CYP2C9 inhibition	-	0.9006	90.06%
CYP2C19 inhibition	-	0.9156	91.56%
CYP2D6 inhibition	-	0.9512	95.12%
CYP1A2 inhibition	-	0.6319	63.19%
CYP2C8 inhibition	-	0.8171	81.71%
CYP inhibitory promiscuity	-	0.8973	89.73%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4212	42.12%
Eye corrosion	-	0.9926	99.26%
Eye irritation	-	0.9777	97.77%
Skin irritation	+	0.6822	68.22%
Skin corrosion	-	0.8869	88.69%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5853	58.53%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.5589	55.89%
skin sensitisation	-	0.7778	77.78%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.5250	52.50%
Acute Oral Toxicity (c)	I	0.5045	50.45%
Estrogen receptor binding	+	0.5950	59.50%
Androgen receptor binding	+	0.6720	67.20%
Thyroid receptor binding	-	0.6365	63.65%
Glucocorticoid receptor binding	-	0.4777	47.77%
Aromatase binding	+	0.5195	51.95%
PPAR gamma	-	0.6460	64.60%
Honey bee toxicity	-	0.7922	79.22%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9783	97.83%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.06%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.90%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.05%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.75%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.59%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.77%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.26%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.33%	86.33%
CHEMBL2581	P07339	Cathepsin D	85.05%	98.95%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.77%	92.94%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.81%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.65%	94.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 101860561
• LOTUS: LTS0258149
• wikiData: Q105130513