[(2S,3R,4S,5R)-2-[2-[(2R,4aR)-4a,8-dimethyl-2,3,4,5,6,7-hexahydro-1H-naphthalen-2-yl]propan-2-yloxy]-4,5-dihydroxyoxan-3-yl] acetate

Details

• Internal ID: 5235b401-e899-472c-a79e-a1a476cc0c74
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: [(2S,3R,4S,5R)-2-[2-[(2R,4aR)-4a,8-dimethyl-2,3,4,5,6,7-hexahydro-1H-naphthalen-2-yl]propan-2-yloxy]-4,5-dihydroxyoxan-3-yl] acetate
• SMILES (Canonical): CC1=C2CC(CCC2(CCC1)C)C(C)(C)OC3C(C(C(CO3)O)O)OC(=O)C
• SMILES (Isomeric): CC1=C2C[C@@H](CC[C@]2(CCC1)C)C(C)(C)O[C@H]3[C@@H]([C@H]([C@@H](CO3)O)O)OC(=O)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/h15,17-20,24-25H,6-12H2,1-5H3/t15-,17-,18+,19-,20+,22-/m1/s1
• InChI Key: QNWIDTXODBSVCO-RAYWZDFNSA-N
• Popularity: 2 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: 2.40
• Atomic LogP (AlogP): 3.10
• 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	+	0.9732	97.32%
Caco-2	-	0.5432	54.32%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8800	88.00%
OATP2B1 inhibitior	-	0.7190	71.90%
OATP1B1 inhibitior	+	0.8482	84.82%
OATP1B3 inhibitior	+	0.8722	87.22%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7318	73.18%
BSEP inhibitior	+	0.7805	78.05%
P-glycoprotein inhibitior	-	0.5650	56.50%
P-glycoprotein substrate	-	0.7136	71.36%
CYP3A4 substrate	+	0.6952	69.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8832	88.32%
CYP3A4 inhibition	-	0.8659	86.59%
CYP2C9 inhibition	-	0.8336	83.36%
CYP2C19 inhibition	-	0.8982	89.82%
CYP2D6 inhibition	-	0.9367	93.67%
CYP1A2 inhibition	-	0.6859	68.59%
CYP2C8 inhibition	-	0.5734	57.34%
CYP inhibitory promiscuity	-	0.9709	97.09%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6427	64.27%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9259	92.59%
Skin irritation	-	0.5909	59.09%
Skin corrosion	-	0.9470	94.70%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6957	69.57%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.8208	82.08%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.7379	73.79%
Acute Oral Toxicity (c)	III	0.4932	49.32%
Estrogen receptor binding	+	0.6963	69.63%
Androgen receptor binding	+	0.5939	59.39%
Thyroid receptor binding	+	0.5707	57.07%
Glucocorticoid receptor binding	+	0.7287	72.87%
Aromatase binding	+	0.6052	60.52%
PPAR gamma	+	0.5368	53.68%
Honey bee toxicity	-	0.7541	75.41%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9788	97.88%

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	97.48%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.04%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.60%	97.25%
CHEMBL2581	P07339	Cathepsin D	92.47%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.22%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.89%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.31%	96.77%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	87.83%	96.38%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.59%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.43%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.34%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.90%	100.00%
CHEMBL5028	O14672	ADAM10	85.04%	97.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.80%	94.00%
CHEMBL1871	P10275	Androgen Receptor	84.29%	96.43%
CHEMBL204	P00734	Thrombin	84.28%	96.01%
CHEMBL5255	O00206	Toll-like receptor 4	83.86%	92.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.23%	86.33%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.49%	93.03%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.17%	97.14%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	81.82%	90.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.76%	97.09%
CHEMBL1914	P06276	Butyrylcholinesterase	80.87%	95.00%

Plants that contains it

• Iphiona mucronata
• Iphiona scabra

Cross-Links

• PubChem: 14756445
• LOTUS: LTS0024579
• wikiData: Q105224686