[(2S,3R,4S,5R)-2-[2-[(2R,4aR,8aR)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-2-yl]propan-2-yloxy]-4,5-dihydroxyoxan-3-yl] acetate

Details

• Internal ID: c71f4ed2-a9a4-4a03-8749-8bdeb0b74112
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: [(2S,3R,4S,5R)-2-[2-[(2R,4aR,8aR)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-2-yl]propan-2-yloxy]-4,5-dihydroxyoxan-3-yl] acetate
• SMILES (Canonical): CC1=CCCC2(C1CC(CC2)C(C)(C)OC3C(C(C(CO3)O)O)OC(=O)C)C
• SMILES (Isomeric): CC1=CCC[C@]2([C@H]1C[C@@H](CC2)C(C)(C)O[C@H]3[C@@H]([C@H]([C@@H](CO3)O)O)OC(=O)C)C
• InChI: InChI=1S/C22H36O6/c1-13-7-6-9-22(5)10-8-15(11-16(13)22)21(3,4)28-20-19(27-14(2)23)18(25)17(24)12-26-20/h7,15-20,24-25H,6,8-12H2,1-5H3/t15-,16+,17-,18+,19-,20+,22-/m1/s1
• InChI Key: NTUCDCCCTFLXCV-TUYITFMESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₆O₆
• Molecular Weight: 396.50 g/mol
• Exact Mass: 396.25118886 g/mol
• Topological Polar Surface Area (TPSA): 85.20 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.95
• H-Bond Acceptor: 6
• 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	+	0.9656	96.56%
Caco-2	-	0.6470	64.70%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8649	86.49%
OATP2B1 inhibitior	-	0.7211	72.11%
OATP1B1 inhibitior	+	0.9104	91.04%
OATP1B3 inhibitior	+	0.8930	89.30%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7568	75.68%
BSEP inhibitior	+	0.8765	87.65%
P-glycoprotein inhibitior	-	0.5746	57.46%
P-glycoprotein substrate	-	0.6706	67.06%
CYP3A4 substrate	+	0.6982	69.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8832	88.32%
CYP3A4 inhibition	-	0.8570	85.70%
CYP2C9 inhibition	-	0.8380	83.80%
CYP2C19 inhibition	-	0.8619	86.19%
CYP2D6 inhibition	-	0.9389	93.89%
CYP1A2 inhibition	-	0.6390	63.90%
CYP2C8 inhibition	+	0.5232	52.32%
CYP inhibitory promiscuity	-	0.9703	97.03%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6586	65.86%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.9613	96.13%
Skin irritation	-	0.5985	59.85%
Skin corrosion	-	0.9508	95.08%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5700	57.00%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.5551	55.51%
skin sensitisation	-	0.8077	80.77%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.7726	77.26%
Acute Oral Toxicity (c)	III	0.4395	43.95%
Estrogen receptor binding	+	0.7728	77.28%
Androgen receptor binding	-	0.5366	53.66%
Thyroid receptor binding	+	0.5610	56.10%
Glucocorticoid receptor binding	+	0.7786	77.86%
Aromatase binding	+	0.5980	59.80%
PPAR gamma	+	0.5808	58.08%
Honey bee toxicity	-	0.7352	73.52%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9762	97.62%

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	98.82%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.87%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.22%	96.77%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.35%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.61%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.15%	89.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.10%	92.94%
CHEMBL2581	P07339	Cathepsin D	87.90%	98.95%
CHEMBL1871	P10275	Androgen Receptor	87.76%	96.43%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.34%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.95%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.71%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.13%	95.56%
CHEMBL5255	O00206	Toll-like receptor 4	84.53%	92.50%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	84.33%	90.93%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.31%	93.04%
CHEMBL5028	O14672	ADAM10	82.79%	97.50%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.33%	97.21%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.26%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	81.38%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.37%	94.00%

Plants that contains it

• Iphiona mucronata
• Iphiona scabra

Cross-Links

• PubChem: 162857709
• LOTUS: LTS0160206
• wikiData: Q105185657