(4S,4aS,5R,8aR)-3,4a,5-trimethyl-5,6,7,8,8a,9-hexahydro-4H-benzo[f][1]benzofuran-4,6-diol

Details

• Internal ID: 48d020db-d7a5-47dc-b368-53c26125b301
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: (4S,4aS,5R,8aR)-3,4a,5-trimethyl-5,6,7,8,8a,9-hexahydro-4H-benzo[f][1]benzofuran-4,6-diol
• SMILES (Canonical): CC1C(CCC2C1(C(C3=C(C2)OC=C3C)O)C)O
• SMILES (Isomeric): C[C@H]1C(CC[C@H]2[C@@]1([C@@H](C3=C(C2)OC=C3C)O)C)O
• InChI: InChI=1S/C15H22O3/c1-8-7-18-12-6-10-4-5-11(16)9(2)15(10,3)14(17)13(8)12/h7,9-11,14,16-17H,4-6H2,1-3H3/t9-,10+,11?,14+,15+/m0/s1
• InChI Key: JWKRZHJQYDUUNQ-WLNJXQACSA-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): 53.60 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.59
• 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	+	0.9948	99.48%
Caco-2	+	0.5619	56.19%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6087	60.87%
OATP2B1 inhibitior	-	0.8556	85.56%
OATP1B1 inhibitior	+	0.9153	91.53%
OATP1B3 inhibitior	+	0.9433	94.33%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.7992	79.92%
P-glycoprotein inhibitior	-	0.9366	93.66%
P-glycoprotein substrate	-	0.7540	75.40%
CYP3A4 substrate	+	0.5582	55.82%
CYP2C9 substrate	-	0.5698	56.98%
CYP2D6 substrate	+	0.3685	36.85%
CYP3A4 inhibition	-	0.8599	85.99%
CYP2C9 inhibition	-	0.7826	78.26%
CYP2C19 inhibition	-	0.7636	76.36%
CYP2D6 inhibition	-	0.9334	93.34%
CYP1A2 inhibition	+	0.5646	56.46%
CYP2C8 inhibition	-	0.6929	69.29%
CYP inhibitory promiscuity	-	0.7560	75.60%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7500	75.00%
Carcinogenicity (trinary)	Non-required	0.4144	41.44%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9803	98.03%
Skin irritation	-	0.6191	61.91%
Skin corrosion	-	0.8866	88.66%
Ames mutagenesis	-	0.6764	67.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.6640	66.40%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.8083	80.83%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.8114	81.14%
Acute Oral Toxicity (c)	III	0.5480	54.80%
Estrogen receptor binding	+	0.6023	60.23%
Androgen receptor binding	+	0.5324	53.24%
Thyroid receptor binding	-	0.5395	53.95%
Glucocorticoid receptor binding	+	0.5397	53.97%
Aromatase binding	-	0.5605	56.05%
PPAR gamma	+	0.6028	60.28%
Honey bee toxicity	-	0.8969	89.69%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.8912	89.12%

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	94.34%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.23%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.66%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.92%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.29%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.89%	100.00%
CHEMBL2581	P07339	Cathepsin D	81.37%	98.95%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	81.35%	86.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.59%	89.00%

Plants that contains it

• Farfugium japonicum
• Petasites japonicus

Cross-Links

• PubChem: 5317428
• NPASS: NPC106650