(4R,4aR,5R)-3,4a,5-trimethyl-4,6,7,9-tetrahydrobenzo[f][1]benzofuran-4,5-diol

Details

• Internal ID: 06b68da6-f31e-409e-9602-16049ccdb440
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: (4R,4aR,5R)-3,4a,5-trimethyl-4,6,7,9-tetrahydrobenzo[f][1]benzofuran-4,5-diol
• SMILES (Canonical): CC1=COC2=C1C(C3(C(=CCCC3(C)O)C2)C)O
• SMILES (Isomeric): CC1=COC2=C1[C@H]([C@]3(C(=CCC[C@@]3(C)O)C2)C)O
• InChI: InChI=1S/C15H20O3/c1-9-8-18-11-7-10-5-4-6-14(2,17)15(10,3)13(16)12(9)11/h5,8,13,16-17H,4,6-7H2,1-3H3/t13-,14-,15-/m1/s1
• InChI Key: OKNQFKPGULYHTO-RBSFLKMASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 53.60 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 2.66
• H-Bond Acceptor: 3
• 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	+	0.9956	99.56%
Caco-2	+	0.7467	74.67%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5683	56.83%
OATP2B1 inhibitior	-	0.8552	85.52%
OATP1B1 inhibitior	+	0.9266	92.66%
OATP1B3 inhibitior	+	0.9678	96.78%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.6229	62.29%
P-glycoprotein inhibitior	-	0.9520	95.20%
P-glycoprotein substrate	-	0.8718	87.18%
CYP3A4 substrate	+	0.5756	57.56%
CYP2C9 substrate	-	0.6075	60.75%
CYP2D6 substrate	-	0.7074	70.74%
CYP3A4 inhibition	-	0.6657	66.57%
CYP2C9 inhibition	-	0.7499	74.99%
CYP2C19 inhibition	-	0.7011	70.11%
CYP2D6 inhibition	-	0.9036	90.36%
CYP1A2 inhibition	+	0.6317	63.17%
CYP2C8 inhibition	+	0.4654	46.54%
CYP inhibitory promiscuity	+	0.5325	53.25%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.4455	44.55%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.7712	77.12%
Skin irritation	-	0.5760	57.60%
Skin corrosion	-	0.9273	92.73%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5711	57.11%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.5623	56.23%
skin sensitisation	-	0.7851	78.51%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.7765	77.65%
Acute Oral Toxicity (c)	III	0.3051	30.51%
Estrogen receptor binding	-	0.5678	56.78%
Androgen receptor binding	+	0.5979	59.79%
Thyroid receptor binding	-	0.5461	54.61%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.6170	61.70%
PPAR gamma	+	0.7030	70.30%
Honey bee toxicity	-	0.9023	90.23%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9905	99.05%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	91.56%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.47%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.65%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.18%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.15%	89.00%
CHEMBL221	P23219	Cyclooxygenase-1	85.89%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.53%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.29%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.55%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.96%	92.94%

Plants that contains it

• Euryops jacksonii

Cross-Links

• PubChem: 101599468
• LOTUS: LTS0270346
• wikiData: Q105193656