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

Details

• Internal ID: 163d5e50-50eb-4cdd-b981-c5de5aafb27d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (4aS,7R,8R,8aS)-8-[2-[(2S)-2-hydroxy-5-oxo-2H-furan-4-yl]ethyl]-4,7,8-trimethyl-1,2,5,6,7,8a-hexahydronaphthalene-4a-carboxylic acid
• SMILES (Canonical): CC1CCC2(C(C1(C)CCC3=CC(OC3=O)O)CCC=C2C)C(=O)O
• SMILES (Isomeric): C[C@@H]1CC[C@@]2([C@H]([C@]1(C)CCC3=C[C@H](OC3=O)O)CCC=C2C)C(=O)O
• InChI: InChI=1S/C20H28O5/c1-12-7-10-20(18(23)24)13(2)5-4-6-15(20)19(12,3)9-8-14-11-16(21)25-17(14)22/h5,11-12,15-16,21H,4,6-10H2,1-3H3,(H,23,24)/t12-,15+,16+,19-,20-/m1/s1
• InChI Key: KRHQWEZBTHQNAB-ZOROFGBHSA-N
• Popularity: 0 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: 3.50
• 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	+	0.9832	98.32%
Caco-2	+	0.6359	63.59%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7122	71.22%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8412	84.12%
OATP1B3 inhibitior	+	0.8389	83.89%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.6303	63.03%
BSEP inhibitior	+	0.6476	64.76%
P-glycoprotein inhibitior	-	0.7763	77.63%
P-glycoprotein substrate	-	0.7997	79.97%
CYP3A4 substrate	+	0.6449	64.49%
CYP2C9 substrate	-	0.8042	80.42%
CYP2D6 substrate	-	0.9000	90.00%
CYP3A4 inhibition	-	0.6594	65.94%
CYP2C9 inhibition	-	0.8278	82.78%
CYP2C19 inhibition	-	0.8723	87.23%
CYP2D6 inhibition	-	0.9460	94.60%
CYP1A2 inhibition	-	0.5928	59.28%
CYP2C8 inhibition	-	0.6229	62.29%
CYP inhibitory promiscuity	-	0.8373	83.73%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5383	53.83%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.9539	95.39%
Skin irritation	+	0.5659	56.59%
Skin corrosion	-	0.9216	92.16%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.7076	70.76%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.4701	47.01%
Acute Oral Toxicity (c)	I	0.3667	36.67%
Estrogen receptor binding	+	0.7874	78.74%
Androgen receptor binding	+	0.5969	59.69%
Thyroid receptor binding	+	0.5833	58.33%
Glucocorticoid receptor binding	+	0.7459	74.59%
Aromatase binding	+	0.7360	73.60%
PPAR gamma	+	0.6402	64.02%
Honey bee toxicity	-	0.8435	84.35%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
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
CHEMBL4040	P28482	MAP kinase ERK2	98.35%	83.82%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.23%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.58%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.16%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.00%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.60%	95.56%
CHEMBL2581	P07339	Cathepsin D	87.85%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.58%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.95%	97.09%
CHEMBL5028	O14672	ADAM10	82.56%	97.50%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 163037834
• LOTUS: LTS0099516
• wikiData: Q105145021