(3S,5S)-9-hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydro-3H-benzo[f][1]benzofuran-2-one

Details

• Internal ID: 6b3d25b5-9622-4f1e-8990-2db30b1551f3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (3S,5S)-9-hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydro-3H-benzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1CCCC2=C(C3=C(C(C(=O)O3)C)C(=C12)C)O
• SMILES (Isomeric): C[C@H]1CCCC2=C(C3=C([C@@H](C(=O)O3)C)C(=C12)C)O
• InChI: InChI=1S/C15H18O3/c1-7-5-4-6-10-11(7)8(2)12-9(3)15(17)18-14(12)13(10)16/h7,9,16H,4-6H2,1-3H3/t7-,9-/m0/s1
• InChI Key: WNVJFXCXPGTUNO-CBAPKCEASA-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: 3.60
• Atomic LogP (AlogP): 3.16
• 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	+	0.9945	99.45%
Caco-2	+	0.7733	77.33%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7379	73.79%
OATP2B1 inhibitior	-	0.8467	84.67%
OATP1B1 inhibitior	+	0.8684	86.84%
OATP1B3 inhibitior	+	0.8819	88.19%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	-	0.9381	93.81%
P-glycoprotein inhibitior	-	0.8609	86.09%
P-glycoprotein substrate	-	0.8777	87.77%
CYP3A4 substrate	+	0.5177	51.77%
CYP2C9 substrate	+	0.6181	61.81%
CYP2D6 substrate	-	0.7774	77.74%
CYP3A4 inhibition	-	0.7636	76.36%
CYP2C9 inhibition	-	0.6159	61.59%
CYP2C19 inhibition	-	0.5137	51.37%
CYP2D6 inhibition	-	0.9282	92.82%
CYP1A2 inhibition	+	0.9238	92.38%
CYP2C8 inhibition	-	0.8323	83.23%
CYP inhibitory promiscuity	-	0.7483	74.83%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5151	51.51%
Eye corrosion	-	0.9845	98.45%
Eye irritation	-	0.5146	51.46%
Skin irritation	-	0.5906	59.06%
Skin corrosion	-	0.8516	85.16%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7478	74.78%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.6053	60.53%
skin sensitisation	-	0.7703	77.03%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.8027	80.27%
Acute Oral Toxicity (c)	III	0.4739	47.39%
Estrogen receptor binding	-	0.4767	47.67%
Androgen receptor binding	+	0.5906	59.06%
Thyroid receptor binding	+	0.5252	52.52%
Glucocorticoid receptor binding	+	0.7464	74.64%
Aromatase binding	-	0.7386	73.86%
PPAR gamma	+	0.5260	52.60%
Honey bee toxicity	-	0.9481	94.81%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9930	99.30%

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	95.59%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.10%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.52%	99.23%
CHEMBL2581	P07339	Cathepsin D	90.18%	98.95%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.46%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.16%	89.00%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	82.83%	90.93%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.58%	93.04%
CHEMBL1951	P21397	Monoamine oxidase A	81.71%	91.49%
CHEMBL5255	O00206	Toll-like receptor 4	81.09%	92.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.22%	100.00%
CHEMBL5905	Q04828	Aldo-keto reductase family 1 member C1	80.14%	91.79%
CHEMBL3238	P23786	Carnitine palmitoyltransferase 2	80.00%	94.05%

Plants that contains it

• Parasenecio hastatus

Cross-Links

• PubChem: 101286248
• LOTUS: LTS0010956
• wikiData: Q105309327