julibroside J29

Details

• Internal ID: c733745d-2185-47c6-8399-f66dacfecd6f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [(2S,3R,4S,5S,6R)-3-[(2S,3R,4S,5S,6S)-5-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-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,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4R,5S,6R)-3-acetamido-6-[[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxymethyl]-4,5-dihydroxyoxan-2-yl]oxy-5-hydroxy-3-[(2E,6R)-2-(hydroxymethyl)-6-methyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyocta-2,7-dienoyl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• SMILES (Canonical): CC1C(C(C(C(O1)OC(C)(CCC=C(CO)C(=O)OC2CC3(C(CC2(C)C)C4=CCC5C6(CCC(C(C6CCC5(C4(CC3O)C)C)(C)C)OC7C(C(C(C(O7)COC8C(C(C(C(O8)C)O)O)OC9C(C(C(CO9)O)O)O)O)O)NC(=O)C)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)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@](C)(CC/C=C(\CO)/C(=O)O[C@H]2C[C@@]3([C@@H](C[C@@]4(C(=CC[C@H]5[C@]4(CC[C@@H]6[C@@]5(CC[C@@H](C6(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO[C@H]8[C@@H]([C@H]([C@H]([C@H](O8)C)O)O)O[C@H]9[C@@H]([C@H]([C@@H](CO9)O)O)O)O)O)NC(=O)C)C)C)[C@@H]3CC2(C)C)C)O)C(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O[C@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)C)O[C@H]1[C@@H]([C@H]([C@@H](O1)CO)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)C=C)O)O)O
• InChI: InChI=1S/C88H141NO43/c1-14-84(10,132-78-66(112)59(105)51(97)33(2)118-78)21-15-16-37(27-90)72(114)125-49-26-88(81(115)131-80-71(62(108)55(101)42(29-92)123-80)130-77-67(113)69(128-76-65(111)60(106)54(100)41(28-91)121-76)68(35(4)120-77)127-75-64(110)56(102)43(30-93)122-75)39(24-82(49,6)7)38-17-18-46-85(11)22-20-48(83(8,9)45(85)19-23-86(46,12)87(38,13)25-47(88)96)126-73-50(89-36(5)94)58(104)57(103)44(124-73)32-117-79-70(61(107)52(98)34(3)119-79)129-74-63(109)53(99)40(95)31-116-74/h14,16-17,33-35,39-71,73-80,90-93,95-113H,1,15,18-32H2,2-13H3,(H,89,94)/b37-16+/t33-,34-,35+,39+,40-,41-,42-,43+,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-,73+,74+,75+,76+,77+,78+,79-,80+,84+,85+,86-,87-,88-/m1/s1
• InChI Key: CPYYSAAISPCOSH-QRROOZJYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈₈H₁₄₁NO₄₃
• Molecular Weight: 1901.00 g/mol
• Exact Mass: 1899.8877321 g/mol
• Topological Polar Surface Area (TPSA): 685.00 Ų
• XlogP: -4.80
• Atomic LogP (AlogP): -7.11
• H-Bond Acceptor: 43
• H-Bond Donor: 24
• Rotatable Bonds: 28

Synonyms

• CHEMBL430035

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6560	65.60%
Caco-2	-	0.8568	85.68%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7180	71.80%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7301	73.01%
OATP1B3 inhibitior	+	0.9110	91.10%
MATE1 inhibitior	-	0.9046	90.46%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9740	97.40%
P-glycoprotein inhibitior	+	0.7421	74.21%
P-glycoprotein substrate	+	0.7907	79.07%
CYP3A4 substrate	+	0.7620	76.20%
CYP2C9 substrate	-	0.8062	80.62%
CYP2D6 substrate	-	0.8809	88.09%
CYP3A4 inhibition	-	0.8370	83.70%
CYP2C9 inhibition	-	0.8658	86.58%
CYP2C19 inhibition	-	0.8791	87.91%
CYP2D6 inhibition	-	0.9363	93.63%
CYP1A2 inhibition	-	0.8935	89.35%
CYP2C8 inhibition	+	0.8499	84.99%
CYP inhibitory promiscuity	-	0.8203	82.03%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.4473	44.73%
Eye corrosion	-	0.9854	98.54%
Eye irritation	-	0.8956	89.56%
Skin irritation	-	0.6919	69.19%
Skin corrosion	-	0.9223	92.23%
Ames mutagenesis	-	0.6770	67.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7503	75.03%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.8471	84.71%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.7760	77.60%
Acute Oral Toxicity (c)	III	0.6662	66.62%
Estrogen receptor binding	-	0.4778	47.78%
Androgen receptor binding	+	0.7668	76.68%
Thyroid receptor binding	+	0.7775	77.75%
Glucocorticoid receptor binding	+	0.8399	83.99%
Aromatase binding	+	0.7834	78.34%
PPAR gamma	+	0.8030	80.30%
Honey bee toxicity	-	0.5896	58.96%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9675	96.75%

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	99.70%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	95.72%	95.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.97%	97.25%
CHEMBL3714130	P46095	G-protein coupled receptor 6	94.75%	97.36%
CHEMBL218	P21554	Cannabinoid CB1 receptor	94.31%	96.61%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.88%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.69%	97.09%
CHEMBL2179	P04062	Beta-glucocerebrosidase	91.15%	85.31%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	91.00%	96.90%
CHEMBL3401	O75469	Pregnane X receptor	90.78%	94.73%
CHEMBL5028	O14672	ADAM10	90.50%	97.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.40%	89.00%
CHEMBL2581	P07339	Cathepsin D	89.86%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.55%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	89.43%	95.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.46%	99.17%
CHEMBL1937	Q92769	Histone deacetylase 2	87.14%	94.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.09%	86.33%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.95%	94.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.80%	95.56%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.12%	89.34%
CHEMBL5255	O00206	Toll-like receptor 4	84.04%	92.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.15%	95.89%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.48%	91.24%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.14%	95.71%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	82.12%	91.03%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	81.72%	95.71%
CHEMBL259	P32245	Melanocortin receptor 4	81.31%	95.38%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.01%	96.21%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.58%	95.83%
CHEMBL233	P35372	Mu opioid receptor	80.40%	97.93%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	80.24%	89.67%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.07%	94.45%
CHEMBL325	Q13547	Histone deacetylase 1	80.06%	95.92%

Plants that contains it

• Acacia victoriae
• Albizia julibrissin

Cross-Links

• PubChem: 44448243
• NPASS: NPC100612
• ChEMBL: CHEMBL430035
• LOTUS: LTS0160957
• wikiData: Q104967857