Dianoside A

Details

• Internal ID: 7b522eb1-66c2-4206-916f-a5ac8d97df1d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (3S,4S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4,6a,6b,11,11,14b-hexamethyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carboxylic acid
• SMILES (Canonical): CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C(=O)O)OC6C(C(C(C(O6)CO)O)O)O)C)C)C2C1)C)C(=O)OC7C(C(C(C(O7)CO)O)O)O)C
• SMILES (Isomeric): C[C@]12CC[C@@H]([C@@]([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)C)(C)C(=O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
• InChI: InChI=1S/C42H66O15/c1-37(2)13-15-42(36(53)57-34-32(50)30(48)28(46)23(19-44)55-34)16-14-39(4)20(21(42)17-37)7-8-24-38(3)11-10-26(41(6,35(51)52)25(38)9-12-40(24,39)5)56-33-31(49)29(47)27(45)22(18-43)54-33/h7,21-34,43-50H,8-19H2,1-6H3,(H,51,52)/t21-,22+,23+,24+,25+,26-,27+,28+,29-,30-,31+,32+,33-,34-,38+,39+,40+,41-,42-/m0/s1
• InChI Key: YYXPXYDYZRXSJH-BEVNDZSHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₆₆O₁₅
• Molecular Weight: 811.00 g/mol
• Exact Mass: 810.44017139 g/mol
• Topological Polar Surface Area (TPSA): 253.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 1.38
• H-Bond Acceptor: 14
• H-Bond Donor: 9
• Rotatable Bonds: 7

Synonyms

• 91652-87-8
• C08941
• CHEBI:4490
• DTXSID60919609
• (3S,4S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4,6a,6b,11,11,14b-hexamethyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carboxylic acid
• Q27106398
• 1-O-[3-(Hexopyranosyloxy)-23-hydroxy-23,28-dioxoolean-12-en-28-yl]hexopyranose

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7181	71.81%
Caco-2	-	0.8811	88.11%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8914	89.14%
OATP2B1 inhibitior	-	0.8712	87.12%
OATP1B1 inhibitior	+	0.7708	77.08%
OATP1B3 inhibitior	-	0.5187	51.87%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5974	59.74%
BSEP inhibitior	+	0.6006	60.06%
P-glycoprotein inhibitior	+	0.7523	75.23%
P-glycoprotein substrate	-	0.8608	86.08%
CYP3A4 substrate	+	0.6960	69.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8776	87.76%
CYP3A4 inhibition	-	0.9061	90.61%
CYP2C9 inhibition	-	0.8653	86.53%
CYP2C19 inhibition	-	0.9130	91.30%
CYP2D6 inhibition	-	0.9498	94.98%
CYP1A2 inhibition	-	0.8749	87.49%
CYP2C8 inhibition	+	0.6297	62.97%
CYP inhibitory promiscuity	-	0.9549	95.49%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6115	61.15%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9090	90.90%
Skin irritation	-	0.6295	62.95%
Skin corrosion	-	0.9453	94.53%
Ames mutagenesis	-	0.8470	84.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6720	67.20%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.8875	88.75%
skin sensitisation	-	0.9028	90.28%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.7465	74.65%
Acute Oral Toxicity (c)	III	0.7689	76.89%
Estrogen receptor binding	+	0.7588	75.88%
Androgen receptor binding	+	0.7272	72.72%
Thyroid receptor binding	-	0.5848	58.48%
Glucocorticoid receptor binding	+	0.6647	66.47%
Aromatase binding	+	0.6161	61.61%
PPAR gamma	+	0.7329	73.29%
Honey bee toxicity	-	0.7598	75.98%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6450	64.50%
Fish aquatic toxicity	+	0.9722	97.22%

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	97.57%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.01%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.88%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.79%	97.09%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	92.21%	95.17%
CHEMBL221	P23219	Cyclooxygenase-1	86.21%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.97%	95.56%
CHEMBL5255	O00206	Toll-like receptor 4	83.91%	92.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.95%	93.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.67%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.15%	95.89%
CHEMBL2581	P07339	Cathepsin D	82.10%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.78%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.65%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.48%	86.33%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.45%	97.36%

Plants that contains it

• Dianthus longicalyx
• Dianthus superbus

Cross-Links

• PubChem: 441919
• LOTUS: LTS0236163
• wikiData: Q27106398