gordonoside N

Details

• Internal ID: 85233984-f763-414c-b833-6426cc379c21
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aR,12aS,14aR,14bR)-8-hydroxy-4,4,6a,6b,11,11,14b-heptamethyl-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-tetradecahydropicen-3-yl]oxy]-4-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
• SMILES (Canonical): CC1(CCC2(C(C1)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)C)OC6C(C(C(C(O6)C(=O)O)O)OC7C(C(C(CO7)O)O)OC8C(C(C(CO8)O)O)O)OC9C(C(C(C(O9)CO)O)O)O)C)C(=O)OC1C(C(C(C(O1)CO)O)O)O)C
• SMILES (Isomeric): C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(C[C@H]([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)O)C)C)(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)C(=O)O)O)O[C@H]8[C@@H]([C@H]([C@H](CO8)O)O)O[C@H]9[C@@H]([C@H]([C@@H](CO9)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
• InChI: InChI=1S/C58H92O28/c1-53(2)14-15-58(52(76)86-49-40(72)37(69)35(67)27(19-60)80-49)23(16-53)22-8-9-29-55(5)12-11-31(54(3,4)28(55)10-13-56(29,6)57(22,7)17-30(58)63)81-51-45(85-48-39(71)36(68)34(66)26(18-59)79-48)42(41(73)43(83-51)46(74)75)82-50-44(33(65)25(62)21-78-50)84-47-38(70)32(64)24(61)20-77-47/h8,23-45,47-51,59-73H,9-21H2,1-7H3,(H,74,75)/t23-,24+,25-,26+,27+,28-,29+,30+,31-,32-,33-,34+,35+,36-,37-,38+,39+,40+,41-,42-,43-,44+,45+,47-,48-,49-,50-,51+,55-,56+,57+,58+/m0/s1
• InChI Key: GNQHWAAORKJVMT-FYPKULKMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₈H₉₂O₂₈
• Molecular Weight: 1237.30 g/mol
• Exact Mass: 1236.57751227 g/mol
• Topological Polar Surface Area (TPSA): 450.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -3.87
• H-Bond Acceptor: 27
• H-Bond Donor: 16
• Rotatable Bonds: 13

Synonyms

• CHEBI:67502
• CHEMBL1782847
• Q27135970
• 1-O-[(3beta,16alpha)-3-{[beta-D-Glucopyranosyl-(1->2)-[beta-D-xylopyranosyl-(1->2)-alpha-L-arabinopyranosyl-(1->3)]-beta-D-glucopyranuronosyl]oxy}-16-hydroxy-28-oxoolean-12-en-28-yl]-beta-D-glucopyranose

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7601	76.01%
Caco-2	-	0.8778	87.78%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8703	87.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.4055	40.55%
OATP1B3 inhibitior	-	0.4610	46.10%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5026	50.26%
BSEP inhibitior	+	0.9381	93.81%
P-glycoprotein inhibitior	+	0.7457	74.57%
P-glycoprotein substrate	-	0.6082	60.82%
CYP3A4 substrate	+	0.7384	73.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8776	87.76%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.8704	87.04%
CYP2C19 inhibition	-	0.9216	92.16%
CYP2D6 inhibition	-	0.9491	94.91%
CYP1A2 inhibition	-	0.9009	90.09%
CYP2C8 inhibition	+	0.7439	74.39%
CYP inhibitory promiscuity	-	0.9733	97.33%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6024	60.24%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.8988	89.88%
Skin irritation	-	0.5876	58.76%
Skin corrosion	-	0.9441	94.41%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7394	73.94%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.9375	93.75%
skin sensitisation	-	0.9013	90.13%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.9341	93.41%
Acute Oral Toxicity (c)	III	0.8023	80.23%
Estrogen receptor binding	+	0.7679	76.79%
Androgen receptor binding	+	0.7460	74.60%
Thyroid receptor binding	+	0.6017	60.17%
Glucocorticoid receptor binding	+	0.7904	79.04%
Aromatase binding	+	0.6533	65.33%
PPAR gamma	+	0.8219	82.19%
Honey bee toxicity	-	0.6624	66.24%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5555	55.55%
Fish aquatic toxicity	+	0.9585	95.85%

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	96.80%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.67%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.24%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.96%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.11%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.79%	97.09%
CHEMBL2581	P07339	Cathepsin D	84.75%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.48%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	83.89%	92.50%
CHEMBL226	P30542	Adenosine A1 receptor	83.67%	95.93%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.52%	96.21%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.12%	93.00%
CHEMBL5028	O14672	ADAM10	81.85%	97.50%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.57%	96.77%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.54%	89.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.07%	94.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.05%	99.17%

Plants that contains it

• Polyspora chrysandra

Cross-Links

• PubChem: 54584203
• LOTUS: LTS0088426
• wikiData: Q27135970