(3R,4S,4aS)-4-[2-(furan-3-yl)ethyl]-3,4-dihydroxy-3,4a,8,8-tetramethyl-6,7-dihydro-5H-naphthalen-2-one

Details

• Internal ID: 163a1e71-74e7-4ca6-8b07-ae36493c3711
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: (3R,4S,4aS)-4-[2-(furan-3-yl)ethyl]-3,4-dihydroxy-3,4a,8,8-tetramethyl-6,7-dihydro-5H-naphthalen-2-one
• SMILES (Canonical): CC1(CCCC2(C1=CC(=O)C(C2(CCC3=COC=C3)O)(C)O)C)C
• SMILES (Isomeric): C[C@]12CCCC(C1=CC(=O)[C@]([C@@]2(CCC3=COC=C3)O)(C)O)(C)C
• InChI: InChI=1S/C20H28O4/c1-17(2)8-5-9-18(3)15(17)12-16(21)19(4,22)20(18,23)10-6-14-7-11-24-13-14/h7,11-13,22-23H,5-6,8-10H2,1-4H3/t18-,19-,20-/m0/s1
• InChI Key: QARMCHBZCFCHAP-UFYCRDLUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₄
• Molecular Weight: 332.40 g/mol
• Exact Mass: 332.19875937 g/mol
• Topological Polar Surface Area (TPSA): 70.70 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.42
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9933	99.33%
Caco-2	+	0.7420	74.20%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7521	75.21%
OATP2B1 inhibitior	-	0.8555	85.55%
OATP1B1 inhibitior	-	0.4394	43.94%
OATP1B3 inhibitior	+	0.9449	94.49%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.8475	84.75%
P-glycoprotein inhibitior	-	0.6876	68.76%
P-glycoprotein substrate	-	0.7820	78.20%
CYP3A4 substrate	+	0.6077	60.77%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8422	84.22%
CYP3A4 inhibition	+	0.6131	61.31%
CYP2C9 inhibition	-	0.7277	72.77%
CYP2C19 inhibition	-	0.6146	61.46%
CYP2D6 inhibition	-	0.9169	91.69%
CYP1A2 inhibition	-	0.6026	60.26%
CYP2C8 inhibition	-	0.6413	64.13%
CYP inhibitory promiscuity	-	0.7796	77.96%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5132	51.32%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.6698	66.98%
Skin irritation	+	0.5468	54.68%
Skin corrosion	-	0.9322	93.22%
Ames mutagenesis	-	0.5670	56.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4735	47.35%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.5626	56.26%
skin sensitisation	-	0.8019	80.19%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.6821	68.21%
Acute Oral Toxicity (c)	I	0.4514	45.14%
Estrogen receptor binding	+	0.7587	75.87%
Androgen receptor binding	+	0.7666	76.66%
Thyroid receptor binding	+	0.6875	68.75%
Glucocorticoid receptor binding	+	0.7112	71.12%
Aromatase binding	+	0.8180	81.80%
PPAR gamma	-	0.4937	49.37%
Honey bee toxicity	-	0.8615	86.15%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9950	99.50%

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	96.71%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.30%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.80%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.70%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.80%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.67%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.62%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.83%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.68%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	81.47%	90.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.24%	94.00%
CHEMBL230	P35354	Cyclooxygenase-2	80.87%	89.63%

Plants that contains it

• Lagopsis supina

Cross-Links

• PubChem: 90670467
• LOTUS: LTS0106142
• wikiData: Q105217571