[(1S,2R,3R,4aR,5S,8aS)-2-hydroxy-4a,5-dimethyl-7-oxo-3-prop-1-en-2-yl-1,2,3,4,5,6,8,8a-octahydronaphthalen-1-yl] (3S)-3-hydroxy-3-methylpent-4-enoate

Details

• Internal ID: b2c7fe36-49a9-42a7-99e2-5a4911f40a1a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: [(1S,2R,3R,4aR,5S,8aS)-2-hydroxy-4a,5-dimethyl-7-oxo-3-prop-1-en-2-yl-1,2,3,4,5,6,8,8a-octahydronaphthalen-1-yl] (3S)-3-hydroxy-3-methylpent-4-enoate
• SMILES (Canonical): CC1CC(=O)CC2C1(CC(C(C2OC(=O)CC(C)(C=C)O)O)C(=C)C)C
• SMILES (Isomeric): C[C@H]1CC(=O)C[C@H]2[C@@]1(C[C@@H]([C@H]([C@H]2OC(=O)C[C@@](C)(C=C)O)O)C(=C)C)C
• InChI: InChI=1S/C21H32O5/c1-7-20(5,25)11-17(23)26-19-16-9-14(22)8-13(4)21(16,6)10-15(12(2)3)18(19)24/h7,13,15-16,18-19,24-25H,1-2,8-11H2,3-6H3/t13-,15+,16+,18+,19-,20+,21+/m0/s1
• InChI Key: XYIIVTMYQZHEOZ-ANUHFAJBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₂O₅
• Molecular Weight: 364.50 g/mol
• Exact Mass: 364.22497412 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.80
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9862	98.62%
Caco-2	+	0.6277	62.77%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7452	74.52%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8512	85.12%
OATP1B3 inhibitior	+	0.8499	84.99%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7872	78.72%
P-glycoprotein inhibitior	-	0.6366	63.66%
P-glycoprotein substrate	-	0.5894	58.94%
CYP3A4 substrate	+	0.6583	65.83%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8647	86.47%
CYP3A4 inhibition	+	0.5119	51.19%
CYP2C9 inhibition	-	0.9130	91.30%
CYP2C19 inhibition	-	0.8228	82.28%
CYP2D6 inhibition	-	0.9516	95.16%
CYP1A2 inhibition	-	0.8919	89.19%
CYP2C8 inhibition	-	0.5689	56.89%
CYP inhibitory promiscuity	-	0.9387	93.87%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9743	97.43%
Carcinogenicity (trinary)	Non-required	0.6574	65.74%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.9115	91.15%
Skin irritation	+	0.5685	56.85%
Skin corrosion	-	0.9535	95.35%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4037	40.37%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.5335	53.35%
skin sensitisation	-	0.7349	73.49%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.5764	57.64%
Acute Oral Toxicity (c)	III	0.3517	35.17%
Estrogen receptor binding	+	0.6390	63.90%
Androgen receptor binding	-	0.5642	56.42%
Thyroid receptor binding	+	0.6417	64.17%
Glucocorticoid receptor binding	+	0.6697	66.97%
Aromatase binding	+	0.5462	54.62%
PPAR gamma	-	0.5959	59.59%
Honey bee toxicity	-	0.7061	70.61%
Biodegradation	-	0.8250	82.50%
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
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.71%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.55%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.08%	96.09%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	93.39%	90.93%
CHEMBL2581	P07339	Cathepsin D	91.25%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.32%	95.56%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	88.80%	89.34%
CHEMBL1951	P21397	Monoamine oxidase A	88.08%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.07%	86.33%
CHEMBL1871	P10275	Androgen Receptor	86.62%	96.43%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.28%	94.45%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.25%	91.07%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.25%	96.77%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.42%	89.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	82.54%	97.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.35%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	82.11%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.03%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	80.85%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.71%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	80.65%	92.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.49%	91.24%

Plants that contains it

• Euryops algoensis

Cross-Links

• PubChem: 163190676
• LOTUS: LTS0200265
• wikiData: Q105344497