(1R,2R,4aS,5R,8aS)-5-[2-(furan-3-yl)ethyl]-2-hydroxy-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid

Details

• Internal ID: 06341483-fdf3-4821-8731-b6b95a3300e4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: (1R,2R,4aS,5R,8aS)-5-[2-(furan-3-yl)ethyl]-2-hydroxy-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• InChI: InChI=1S/C20H28O4/c1-13-4-7-16-19(2,10-8-17(21)20(16,3)18(22)23)15(13)6-5-14-9-11-24-12-14/h9,11-12,15-17,21H,1,4-8,10H2,2-3H3,(H,22,23)/t15-,16+,17-,19+,20-/m1/s1
• InChI Key: FUWDWKQNRJAIAJ-FPPGBKCQSA-N
• Popularity: 2 references 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: 4.10
• Atomic LogP (AlogP): 4.05
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9829	98.29%
Caco-2	+	0.8074	80.74%
Blood Brain Barrier	+	0.5527	55.27%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6185	61.85%
OATP2B1 inhibitior	-	0.8652	86.52%
OATP1B1 inhibitior	+	0.7693	76.93%
OATP1B3 inhibitior	+	0.8907	89.07%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7820	78.20%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.7099	70.99%
P-glycoprotein substrate	-	0.7020	70.20%
CYP3A4 substrate	+	0.6639	66.39%
CYP2C9 substrate	-	0.8178	81.78%
CYP2D6 substrate	-	0.8168	81.68%
CYP3A4 inhibition	+	0.6570	65.70%
CYP2C9 inhibition	-	0.8548	85.48%
CYP2C19 inhibition	-	0.7867	78.67%
CYP2D6 inhibition	-	0.9295	92.95%
CYP1A2 inhibition	-	0.7084	70.84%
CYP2C8 inhibition	+	0.5539	55.39%
CYP inhibitory promiscuity	-	0.7160	71.60%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5603	56.03%
Eye corrosion	-	0.9937	99.37%
Eye irritation	-	0.9186	91.86%
Skin irritation	+	0.5364	53.64%
Skin corrosion	-	0.9176	91.76%
Ames mutagenesis	-	0.8270	82.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7955	79.55%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.7976	79.76%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.8264	82.64%
Acute Oral Toxicity (c)	I	0.6172	61.72%
Estrogen receptor binding	+	0.7302	73.02%
Androgen receptor binding	+	0.6806	68.06%
Thyroid receptor binding	+	0.6955	69.55%
Glucocorticoid receptor binding	+	0.8138	81.38%
Aromatase binding	+	0.6415	64.15%
PPAR gamma	+	0.5673	56.73%
Honey bee toxicity	-	0.9257	92.57%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	98.08%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.31%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.88%	91.11%
CHEMBL2581	P07339	Cathepsin D	90.16%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.17%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	84.49%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.39%	97.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.60%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.96%	86.33%
CHEMBL5028	O14672	ADAM10	81.57%	97.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.41%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.69%	92.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.64%	89.00%

Plants that contains it

• Gutierrezia sarothrae

Cross-Links

• PubChem: 163027311
• LOTUS: LTS0071536
• wikiData: Q105002089