methyl (1R,2E,4S,5R,9R,11R,12R)-1-hydroxy-8,12-dimethyl-11-[(E)-3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy-5-propan-2-yl-15-oxatricyclo[10.2.1.04,9]pentadeca-2,7,13-triene-2-carboxylate

Details

• Internal ID: 7b6c694b-b93e-47d4-ae3b-69c0e2aebb63
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: methyl (1R,2E,4S,5R,9R,11R,12R)-1-hydroxy-8,12-dimethyl-11-[(E)-3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy-5-propan-2-yl-15-oxatricyclo[10.2.1.04,9]pentadeca-2,7,13-triene-2-carboxylate
• SMILES (Canonical): CC1=CCC(C2C1CC(C3(C=CC(O3)(C(=C2)C(=O)OC)O)C)OC(=O)C=CC4=CN(C=N4)C)C(C)C
• SMILES (Isomeric): CC1=CC[C@@H]([C@@H]/2[C@H]1C[C@H]([C@]3(C=C[C@@](O3)(/C(=C2)/C(=O)OC)O)C)OC(=O)/C=C/C4=CN(C=N4)C)C(C)C
• InChI: InChI=1S/C28H36N2O6/c1-17(2)20-9-7-18(3)21-14-24(35-25(31)10-8-19-15-30(5)16-29-19)27(4)11-12-28(33,36-27)23(13-22(20)21)26(32)34-6/h7-8,10-13,15-17,20-22,24,33H,9,14H2,1-6H3/b10-8+,23-13-/t20-,21+,22-,24-,27-,28-/m1/s1
• InChI Key: VHZOZCRALQEBDG-BVHDLFJRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₆N₂O₆
• Molecular Weight: 496.60 g/mol
• Exact Mass: 496.25733687 g/mol
• Topological Polar Surface Area (TPSA): 99.90 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.74
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9682	96.82%
Caco-2	-	0.6907	69.07%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.3837	38.37%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8604	86.04%
OATP1B3 inhibitior	+	0.9081	90.81%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9779	97.79%
P-glycoprotein inhibitior	+	0.8418	84.18%
P-glycoprotein substrate	+	0.6513	65.13%
CYP3A4 substrate	+	0.7124	71.24%
CYP2C9 substrate	-	0.6119	61.19%
CYP2D6 substrate	-	0.8887	88.87%
CYP3A4 inhibition	-	0.6815	68.15%
CYP2C9 inhibition	-	0.7648	76.48%
CYP2C19 inhibition	-	0.7258	72.58%
CYP2D6 inhibition	-	0.8608	86.08%
CYP1A2 inhibition	-	0.6306	63.06%
CYP2C8 inhibition	+	0.6932	69.32%
CYP inhibitory promiscuity	-	0.7941	79.41%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8200	82.00%
Carcinogenicity (trinary)	Danger	0.4126	41.26%
Eye corrosion	-	0.9834	98.34%
Eye irritation	-	0.9425	94.25%
Skin irritation	-	0.7627	76.27%
Skin corrosion	-	0.9266	92.66%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7097	70.97%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.8411	84.11%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.8109	81.09%
Acute Oral Toxicity (c)	III	0.6085	60.85%
Estrogen receptor binding	+	0.7438	74.38%
Androgen receptor binding	+	0.6469	64.69%
Thyroid receptor binding	+	0.6950	69.50%
Glucocorticoid receptor binding	+	0.7740	77.40%
Aromatase binding	+	0.5766	57.66%
PPAR gamma	+	0.7439	74.39%
Honey bee toxicity	-	0.7688	76.88%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.8879	88.79%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.73%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.68%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.53%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.36%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.95%	86.33%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	89.83%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.38%	91.07%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.21%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.82%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.03%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.74%	95.89%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	85.93%	97.21%
CHEMBL2581	P07339	Cathepsin D	85.85%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.04%	96.00%
CHEMBL4208	P20618	Proteasome component C5	85.04%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.78%	99.23%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.38%	93.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.52%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.85%	97.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.62%	95.89%
CHEMBL240	Q12809	HERG	82.61%	89.76%
CHEMBL3401	O75469	Pregnane X receptor	81.28%	94.73%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.08%	96.77%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.31%	97.50%
CHEMBL1937	Q92769	Histone deacetylase 2	80.19%	94.75%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 163074099
• LOTUS: LTS0016448
• wikiData: Q105286697