Avicin D

Details

• Internal ID: 90b30401-5c75-40e7-be94-ae5f8e8443a5
• 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-3-[(2E,6R)-6-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-5-[(2E,6R)-6-hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoyl]oxy-6-methyloxan-2-yl]oxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoyl]oxy-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3CCC4(C(C3(C)C)CCC5(C4CC=C6C5(CC(C7(C6CC(C(C7)OC(=O)C(=CCCC(C)(C=C)OC8C(C(C(C(O8)C)OC(=O)C(=CCCC(C)(C=C)O)CO)O)O)CO)(C)C)C(=O)OC9C(C(C(C(O9)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)O)C)C)C)NC(=O)C)O)O)OC1C(C(C(CO1)O)O)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)O[C@H]3CC[C@]4([C@H](C3(C)C)CC[C@@]5([C@@H]4CC=C6[C@]5(C[C@H]([C@@]7([C@H]6CC([C@H](C7)OC(=O)/C(=C/CC[C@](C)(C=C)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)C)OC(=O)/C(=C/CC[C@](C)(C=C)O)/CO)O)O)/CO)(C)C)C(=O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)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)O)C)C)C)NC(=O)C)O)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)O)O
• InChI: InChI=1S/C98H155NO46/c1-16-93(11,127)26-18-20-45(34-101)81(125)139-75-41(4)132-87(73(122)69(75)118)145-94(12,17-2)27-19-21-44(33-100)80(124)137-57-32-98(90(126)144-89-79(68(117)62(111)50(36-103)135-89)143-86-74(123)77(141-85-72(121)66(115)61(110)49(35-102)133-85)76(42(5)131-86)140-84-71(120)63(112)51(37-104)134-84)47(30-91(57,7)8)46-22-23-54-95(13)28-25-56(92(9,10)53(95)24-29-96(54,14)97(46,15)31-55(98)107)138-82-58(99-43(6)105)65(114)64(113)52(136-82)39-129-88-78(67(116)59(108)40(3)130-88)142-83-70(119)60(109)48(106)38-128-83/h16-17,20-22,40-42,47-79,82-89,100-104,106-123,127H,1-2,18-19,23-39H2,3-15H3,(H,99,105)/b44-21+,45-20+/t40-,41-,42+,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-,82+,83+,84+,85+,86+,87+,88-,89+,93+,94+,95+,96-,97-,98-/m1/s1
• InChI Key: HKEDBKXRDHFCFB-LUAQNYIXSA-N
• Popularity: 12 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉₈H₁₅₅NO₄₆
• Molecular Weight: 2083.30 g/mol
• Exact Mass: 2082.9853813 g/mol
• Topological Polar Surface Area (TPSA): 732.00 Ų
• XlogP: -3.90
• Atomic LogP (AlogP): -5.92
• H-Bond Acceptor: 46
• H-Bond Donor: 25
• Rotatable Bonds: 35

Synonyms

• Elliptoside E
• 69451KN1RO
• UNII-69451KN1RO
• 197787-20-5
• CHEMBL508651
• DTXSID10173471

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6560	65.60%
Caco-2	-	0.8561	85.61%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7180	71.80%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7424	74.24%
OATP1B3 inhibitior	+	0.9110	91.10%
MATE1 inhibitior	-	0.9046	90.46%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9686	96.86%
P-glycoprotein inhibitior	+	0.7419	74.19%
P-glycoprotein substrate	+	0.8081	80.81%
CYP3A4 substrate	+	0.7642	76.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8831	88.31%
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	+	0.8584	85.84%
CYP inhibitory promiscuity	-	0.8203	82.03%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.4473	44.73%
Eye corrosion	-	0.9854	98.54%
Eye irritation	-	0.8954	89.54%
Skin irritation	-	0.6919	69.19%
Skin corrosion	-	0.9223	92.23%
Ames mutagenesis	-	0.6570	65.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7257	72.57%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	-	0.6000	60.00%
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	-	0.8138	81.38%
Acute Oral Toxicity (c)	III	0.6662	66.62%
Estrogen receptor binding	-	0.5911	59.11%
Androgen receptor binding	+	0.7695	76.95%
Thyroid receptor binding	+	0.8058	80.58%
Glucocorticoid receptor binding	+	0.8514	85.14%
Aromatase binding	+	0.8118	81.18%
PPAR gamma	+	0.8075	80.75%
Honey bee toxicity	-	0.5920	59.20%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
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	99.66%	91.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	96.87%	97.36%
CHEMBL226	P30542	Adenosine A1 receptor	94.01%	95.93%
CHEMBL3401	O75469	Pregnane X receptor	93.94%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.42%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.16%	96.09%
CHEMBL5028	O14672	ADAM10	92.14%	97.50%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	91.99%	96.90%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.90%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.20%	89.00%
CHEMBL2179	P04062	Beta-glucocerebrosidase	90.99%	85.31%
CHEMBL218	P21554	Cannabinoid CB1 receptor	89.28%	96.61%
CHEMBL2581	P07339	Cathepsin D	89.19%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.76%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	87.99%	94.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.76%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.66%	99.17%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.52%	95.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.10%	94.33%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	85.51%	97.21%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.01%	96.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.51%	95.56%
CHEMBL1871	P10275	Androgen Receptor	84.14%	96.43%
CHEMBL5255	O00206	Toll-like receptor 4	83.81%	92.50%
CHEMBL325	Q13547	Histone deacetylase 1	82.72%	95.92%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.62%	95.89%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.35%	96.95%
CHEMBL259	P32245	Melanocortin receptor 4	81.98%	95.38%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.72%	91.24%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.67%	89.34%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	81.57%	89.67%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.17%	93.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.87%	91.07%
CHEMBL4530	P00488	Coagulation factor XIII	80.16%	96.00%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	80.04%	95.71%

Plants that contains it

• Acacia victoriae
• Archidendron ellipticum

Cross-Links

• PubChem: 44566777
• LOTUS: LTS0271777
• wikiData: Q27264310