(4aR,5S,6R,8aR)-5-[2-[(2R)-2-hydroxy-5-oxo-2H-furan-4-yl]ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid

Details

• Internal ID: 4bc5ea77-1d57-450e-934e-6bed325a7def
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (4aR,5S,6R,8aR)-5-[2-[(2R)-2-hydroxy-5-oxo-2H-furan-4-yl]ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid
• InChI: InChI=1S/C20H28O5/c1-12-7-9-20(3)14(17(22)23)5-4-6-15(20)19(12,2)10-8-13-11-16(21)25-18(13)24/h5,11-12,15-16,21H,4,6-10H2,1-3H3,(H,22,23)/t12-,15-,16-,19+,20+/m1/s1
• InChI Key: RHLDHPZFWIWCSQ-OZZRQTCFSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₅
• Molecular Weight: 348.40 g/mol
• Exact Mass: 348.19367399 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 3.43
• H-Bond Acceptor: 4
• 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	+	0.9758	97.58%
Caco-2	+	0.6665	66.65%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6457	64.57%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8738	87.38%
OATP1B3 inhibitior	+	0.9138	91.38%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.5771	57.71%
BSEP inhibitior	-	0.6123	61.23%
P-glycoprotein inhibitior	-	0.7865	78.65%
P-glycoprotein substrate	-	0.8387	83.87%
CYP3A4 substrate	+	0.6083	60.83%
CYP2C9 substrate	-	0.8042	80.42%
CYP2D6 substrate	-	0.9000	90.00%
CYP3A4 inhibition	-	0.7166	71.66%
CYP2C9 inhibition	-	0.8667	86.67%
CYP2C19 inhibition	-	0.9042	90.42%
CYP2D6 inhibition	-	0.9424	94.24%
CYP1A2 inhibition	-	0.5100	51.00%
CYP2C8 inhibition	-	0.7113	71.13%
CYP inhibitory promiscuity	-	0.8150	81.50%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4884	48.84%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.9448	94.48%
Skin irritation	+	0.6182	61.82%
Skin corrosion	-	0.9120	91.20%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4816	48.16%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.5181	51.81%
skin sensitisation	-	0.7267	72.67%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.6377	63.77%
Acute Oral Toxicity (c)	III	0.4210	42.10%
Estrogen receptor binding	+	0.7888	78.88%
Androgen receptor binding	-	0.4903	49.03%
Thyroid receptor binding	+	0.6217	62.17%
Glucocorticoid receptor binding	+	0.7405	74.05%
Aromatase binding	+	0.7806	78.06%
PPAR gamma	+	0.6904	69.04%
Honey bee toxicity	-	0.7688	76.88%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
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
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.11%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.06%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.53%	96.09%
CHEMBL2581	P07339	Cathepsin D	91.21%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.43%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.95%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.54%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.34%	99.23%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.65%	93.00%
CHEMBL5028	O14672	ADAM10	80.80%	97.50%

Plants that contains it

• Grangea maderaspatana

Cross-Links

• PubChem: 163057506
• LOTUS: LTS0270449
• wikiData: Q105236461