Julibroside I

Details

• Internal ID: 18e34ee5-ce30-4f43-8729-c4e4621c883c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [3-[5-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxy-6-methyl-4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] (3S,4aR,5R,6aR,6bR,10S,12aR)-10-[6-[[4,5-dihydroxy-6-methyl-3-(3,4,5-trihydroxyoxan-2-yl)oxyoxan-2-yl]oxymethyl]-4,5-dihydroxy-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3-[(2E,6S)-6-[5-[(2E,6S)-2,6-dimethyl-6-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyocta-2,7-dienoyl]oxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-2,6-dimethylocta-2,7-dienoyl]oxy-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14,14a,14b-hexadecahydropicene-4a-carboxylate
• SMILES (Canonical): CC1C(C(C(C(O1)OC(C)(CCC=C(C)C(=O)OC2C(OC(C(C2O)O)OC(C)(CCC=C(C)C(=O)OC3CC4(C(CC3(C)C)C5CCC6C7(CCC(C(C7CCC6(C5(CC4O)C)C)(C)C)OC8C(C(C(C(O8)COC9C(C(C(C(O9)C)O)O)OC1C(C(C(CO1)O)O)O)O)O)OC1C(C(C(C(O1)CO)O)O)O)C)C(=O)OC1C(C(C(C(O1)CO)O)O)OC1C(C(C(C(O1)C)OC1C(C(C(O1)CO)O)O)OC1C(C(C(C(O1)CO)O)O)O)O)C=C)C)C=C)O)O)O
• SMILES (Isomeric): CC1C(C(C(C(O1)O[C@@](C)(CC/C=C(\C)/C(=O)OC2C(OC(C(C2O)O)O[C@@](C)(CC/C=C(\C)/C(=O)O[C@H]3C[C@@]4([C@@H](C[C@@]5(C(C4CC3(C)C)CCC6[C@]5(CCC7[C@@]6(CC[C@@H](C7(C)C)OC8C(C(C(C(O8)COC9C(C(C(C(O9)C)O)O)OC1C(C(C(CO1)O)O)O)O)O)OC1C(C(C(C(O1)CO)O)O)O)C)C)C)O)C(=O)OC1C(C(C(C(O1)CO)O)O)OC1C(C(C(C(O1)C)OC1C(C(C(O1)CO)O)O)OC1C(C(C(C(O1)CO)O)O)O)O)C=C)C)C=C)O)O)O
• InChI: InChI=1S/C108H174O53/c1-18-103(13,160-95-79(134)68(123)60(115)43(5)142-95)29-21-23-42(4)89(138)153-82-45(7)145-96(80(135)74(82)129)161-104(14,19-2)28-20-22-41(3)88(137)151-59-34-108(100(139)159-99-87(72(127)65(120)52(37-111)149-99)158-94-81(136)84(155-92-77(132)69(124)63(118)50(35-109)146-92)83(46(8)144-94)154-91-76(131)66(121)53(38-112)148-91)48(32-101(59,9)10)47-24-25-56-105(15)30-27-58(102(11,12)55(105)26-31-106(56,16)107(47,17)33-57(108)114)152-98-86(157-93-78(133)70(125)64(119)51(36-110)147-93)73(128)67(122)54(150-98)40-141-97-85(71(126)61(116)44(6)143-97)156-90-75(130)62(117)49(113)39-140-90/h18-19,22-23,43-87,90-99,109-136H,1-2,20-21,24-40H2,3-17H3/b41-22+,42-23+/t43?,44?,45?,46?,47?,48?,49?,50?,51?,52?,53?,54?,55?,56?,57-,58+,59+,60?,61?,62?,63?,64?,65?,66?,67?,68?,69?,70?,71?,72?,73?,74?,75?,76?,77?,78?,79?,80?,81?,82?,83?,84?,85?,86?,87?,90?,91?,92?,93?,94?,95?,96?,97?,98?,99?,103-,104-,105+,106-,107-,108-/m1/s1
• InChI Key: IDRKKIVDGBXFBA-HDMINGSQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀₈H₁₇₄O₅₃
• Molecular Weight: 2320.50 g/mol
• Exact Mass: 2320.0953852 g/mol
• Topological Polar Surface Area (TPSA): 821.00 Ų
• XlogP: -3.10
• Atomic LogP (AlogP): -7.25
• H-Bond Acceptor: 53
• H-Bond Donor: 28
• Rotatable Bonds: 37

Synonyms

• NSC722901
• NSC-722901

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7725	77.25%
Caco-2	-	0.8560	85.60%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8234	82.34%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7784	77.84%
OATP1B3 inhibitior	+	0.8709	87.09%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.9560	95.60%
P-glycoprotein inhibitior	+	0.7420	74.20%
P-glycoprotein substrate	+	0.7606	76.06%
CYP3A4 substrate	+	0.7633	76.33%
CYP2C9 substrate	-	0.8028	80.28%
CYP2D6 substrate	-	0.8775	87.75%
CYP3A4 inhibition	-	0.7760	77.60%
CYP2C9 inhibition	-	0.8148	81.48%
CYP2C19 inhibition	-	0.8933	89.33%
CYP2D6 inhibition	-	0.9384	93.84%
CYP1A2 inhibition	-	0.9028	90.28%
CYP2C8 inhibition	+	0.8307	83.07%
CYP inhibitory promiscuity	-	0.9484	94.84%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5711	57.11%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.8954	89.54%
Skin irritation	+	0.5086	50.86%
Skin corrosion	-	0.9351	93.51%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7291	72.91%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.5798	57.98%
skin sensitisation	-	0.8940	89.40%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.9603	96.03%
Acute Oral Toxicity (c)	III	0.4931	49.31%
Estrogen receptor binding	-	0.5628	56.28%
Androgen receptor binding	+	0.7716	77.16%
Thyroid receptor binding	+	0.8044	80.44%
Glucocorticoid receptor binding	+	0.8441	84.41%
Aromatase binding	+	0.8003	80.03%
PPAR gamma	+	0.8042	80.42%
Honey bee toxicity	-	0.5763	57.63%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9823	98.23%

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	99.21%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.19%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	95.78%	96.61%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.20%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	93.95%	95.93%
CHEMBL3714130	P46095	G-protein coupled receptor 6	93.90%	97.36%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	93.35%	91.24%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.79%	86.33%
CHEMBL2581	P07339	Cathepsin D	91.49%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.35%	97.09%
CHEMBL233	P35372	Mu opioid receptor	91.23%	97.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.64%	89.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	88.52%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.36%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	88.06%	93.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.00%	92.94%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	87.80%	92.88%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	87.14%	95.71%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	87.00%	96.90%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.39%	95.50%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.63%	93.04%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	85.31%	95.71%
CHEMBL5255	O00206	Toll-like receptor 4	85.25%	92.50%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	84.82%	97.86%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	84.63%	98.75%
CHEMBL325	Q13547	Histone deacetylase 1	84.27%	95.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.14%	95.56%
CHEMBL5028	O14672	ADAM10	83.96%	97.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.80%	99.17%
CHEMBL5957	P21589	5'-nucleotidase	83.74%	97.78%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.16%	97.14%
CHEMBL1871	P10275	Androgen Receptor	82.26%	96.43%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.79%	94.33%
CHEMBL203	P00533	Epidermal growth factor receptor erbB1	81.73%	97.34%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	81.60%	100.00%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	81.33%	85.83%
CHEMBL1937	Q92769	Histone deacetylase 2	81.11%	94.75%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.07%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.83%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	80.70%	91.19%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.63%	96.95%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	80.50%	97.29%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.32%	86.92%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.20%	92.62%

Plants that contains it

• Albizia julibrissin

Cross-Links

• PubChem: 5352113
• NPASS: NPC211035
• LOTUS: LTS0227920
• wikiData: Q105111474