Jasmolactone B

Details

• Internal ID: 841b1134-fb8f-4ed5-b159-99a3091ee749
• Taxonomy: Benzenoids > Phenols > Tyrosols and derivatives
• IUPAC Name: 2-(3,4-dihydroxyphenyl)ethyl (1R,4aS,9S,9aS)-9-[2-(3,4-dihydroxyphenyl)ethoxy]-1-hydroxy-6-oxo-1,4a,5,8,9,9a-hexahydropyrano[3,4-d]oxepine-4-carboxylate
• SMILES (Canonical): C1C2C(C(COC1=O)OCCC3=CC(=C(C=C3)O)O)C(OC=C2C(=O)OCCC4=CC(=C(C=C4)O)O)O
• SMILES (Isomeric): C1[C@H]2[C@@H]([C@@H](COC1=O)OCCC3=CC(=C(C=C3)O)O)[C@@H](OC=C2C(=O)OCCC4=CC(=C(C=C4)O)O)O
• InChI: InChI=1S/C26H28O11/c27-18-3-1-14(9-20(18)29)5-7-34-22-13-36-23(31)11-16-17(12-37-26(33)24(16)22)25(32)35-8-6-15-2-4-19(28)21(30)10-15/h1-4,9-10,12,16,22,24,26-30,33H,5-8,11,13H2/t16-,22-,24+,26-/m1/s1
• InChI Key: GJLGUDQPCIWEPW-MATHTASDSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₈O₁₁
• Molecular Weight: 516.50 g/mol
• Exact Mass: 516.16316171 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.63
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

• 2-(3,4-dihydroxyphenyl)ethyl (1R,4aS,9S,9aS)-9-(2-(3,4-dihydroxyphenyl)ethoxy)-1-hydroxy-6-oxo-1,4a,5,8,9,9a-hexahydropyrano(3,4-d)oxepine-4-carboxylate
• 2-(3,4-dihydroxyphenyl)ethyl (1R,4aS,9S,9aS)-9-[2-(3,4-dihydroxyphenyl)ethoxy]-1-hydroxy-6-oxo-1,4a,5,8,9,9a-hexahydropyrano[3,4-d]oxepine-4-carboxylate
• RefChem:150362
• 125339-16-4
• CHEMBL530342

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6063	60.63%
Caco-2	-	0.8939	89.39%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8494	84.94%
OATP2B1 inhibitior	-	0.8587	85.87%
OATP1B1 inhibitior	+	0.8732	87.32%
OATP1B3 inhibitior	+	0.9493	94.93%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7146	71.46%
P-glycoprotein inhibitior	+	0.7507	75.07%
P-glycoprotein substrate	-	0.6042	60.42%
CYP3A4 substrate	+	0.6174	61.74%
CYP2C9 substrate	-	0.7946	79.46%
CYP2D6 substrate	-	0.8537	85.37%
CYP3A4 inhibition	-	0.8396	83.96%
CYP2C9 inhibition	-	0.7038	70.38%
CYP2C19 inhibition	+	0.5570	55.70%
CYP2D6 inhibition	-	0.8143	81.43%
CYP1A2 inhibition	+	0.5214	52.14%
CYP2C8 inhibition	+	0.6757	67.57%
CYP inhibitory promiscuity	-	0.8234	82.34%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6580	65.80%
Eye corrosion	-	0.9870	98.70%
Eye irritation	-	0.8917	89.17%
Skin irritation	-	0.8268	82.68%
Skin corrosion	-	0.9603	96.03%
Ames mutagenesis	+	0.6463	64.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.4836	48.36%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	-	0.6947	69.47%
skin sensitisation	-	0.8011	80.11%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.6261	62.61%
Acute Oral Toxicity (c)	III	0.4095	40.95%
Estrogen receptor binding	+	0.7110	71.10%
Androgen receptor binding	+	0.7734	77.34%
Thyroid receptor binding	-	0.5513	55.13%
Glucocorticoid receptor binding	+	0.5750	57.50%
Aromatase binding	-	0.5560	55.60%
PPAR gamma	+	0.6145	61.45%
Honey bee toxicity	-	0.7250	72.50%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6350	63.50%
Fish aquatic toxicity	+	0.9893	98.93%

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	98.53%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.14%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.95%	94.45%
CHEMBL2581	P07339	Cathepsin D	91.82%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.62%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	90.54%	91.49%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.65%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	88.48%	90.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.14%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.88%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.81%	97.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.11%	96.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.88%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.59%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	84.03%	91.19%
CHEMBL3194	P02766	Transthyretin	81.96%	90.71%
CHEMBL3891	P07384	Calpain 1	81.31%	93.04%
CHEMBL4040	P28482	MAP kinase ERK2	81.26%	83.82%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	80.80%	96.37%
CHEMBL4208	P20618	Proteasome component C5	80.80%	90.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.31%	92.62%

Plants that contains it

• Jasminum multiflorum

Cross-Links

• PubChem: 11049569
• LOTUS: LTS0037264
• wikiData: Q105009462