[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl] (4aS,7S,8R,8aS)-4,7,8-trimethyl-8-[2-(5-oxo-2H-furan-3-yl)ethyl]-1,2,5,6,7,8a-hexahydronaphthalene-4a-carboxylate

Details

• Internal ID: eb4a420e-394d-4f15-a6ac-a929b3adb854
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: [(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl] (4aS,7S,8R,8aS)-4,7,8-trimethyl-8-[2-(5-oxo-2H-furan-3-yl)ethyl]-1,2,5,6,7,8a-hexahydronaphthalene-4a-carboxylate
• SMILES (Canonical): CC1CCC2(C(C1(C)CCC3=CC(=O)OC3)CCC=C2C)C(=O)OC4C(C(C(CO4)O)O)O
• SMILES (Isomeric): C[C@H]1CC[C@@]2([C@H]([C@]1(C)CCC3=CC(=O)OC3)CCC=C2C)C(=O)O[C@H]4[C@@H]([C@H]([C@H](CO4)O)O)O
• InChI: InChI=1S/C25H36O8/c1-14-7-10-25(23(30)33-22-21(29)20(28)17(26)13-32-22)15(2)5-4-6-18(25)24(14,3)9-8-16-11-19(27)31-12-16/h5,11,14,17-18,20-22,26,28-29H,4,6-10,12-13H2,1-3H3/t14-,17-,18-,20-,21+,22-,24+,25+/m0/s1
• InChI Key: HXIWGPICAFPUEN-YFCRTGJWSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₆O₈
• Molecular Weight: 464.50 g/mol
• Exact Mass: 464.24101810 g/mol
• Topological Polar Surface Area (TPSA): 123.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.01
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7884	78.84%
Caco-2	-	0.7317	73.17%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8283	82.83%
OATP2B1 inhibitior	-	0.7156	71.56%
OATP1B1 inhibitior	+	0.8511	85.11%
OATP1B3 inhibitior	+	0.9450	94.50%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6271	62.71%
BSEP inhibitior	+	0.5610	56.10%
P-glycoprotein inhibitior	-	0.4851	48.51%
P-glycoprotein substrate	-	0.5402	54.02%
CYP3A4 substrate	+	0.7037	70.37%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8881	88.81%
CYP3A4 inhibition	-	0.9039	90.39%
CYP2C9 inhibition	-	0.9076	90.76%
CYP2C19 inhibition	-	0.9260	92.60%
CYP2D6 inhibition	-	0.9471	94.71%
CYP1A2 inhibition	-	0.9247	92.47%
CYP2C8 inhibition	+	0.6136	61.36%
CYP inhibitory promiscuity	-	0.9539	95.39%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5499	54.99%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9545	95.45%
Skin irritation	+	0.5646	56.46%
Skin corrosion	-	0.9395	93.95%
Ames mutagenesis	+	0.5046	50.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.5631	56.31%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.5997	59.97%
skin sensitisation	-	0.9214	92.14%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.7673	76.73%
Acute Oral Toxicity (c)	I	0.7155	71.55%
Estrogen receptor binding	+	0.7878	78.78%
Androgen receptor binding	+	0.6922	69.22%
Thyroid receptor binding	-	0.5812	58.12%
Glucocorticoid receptor binding	+	0.7628	76.28%
Aromatase binding	+	0.7641	76.41%
PPAR gamma	+	0.5998	59.98%
Honey bee toxicity	-	0.7444	74.44%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9741	97.41%

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	97.70%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.04%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	94.28%	83.82%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.08%	97.25%
CHEMBL2581	P07339	Cathepsin D	93.32%	98.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.93%	96.61%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.32%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.16%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.83%	95.56%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.23%	96.47%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.32%	96.77%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.81%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.25%	89.00%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	85.96%	83.57%
CHEMBL5028	O14672	ADAM10	84.32%	97.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.18%	99.23%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	83.35%	97.33%
CHEMBL226	P30542	Adenosine A1 receptor	82.46%	95.93%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	82.17%	86.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.81%	91.07%

Plants that contains it

• Gutierrezia dracunculoides
• Gutierrezia texana

Cross-Links

• PubChem: 101712444
• LOTUS: LTS0150201
• wikiData: Q105035030