Tragopogonsaponin D

Details

• Internal ID: 45d00645-7cee-471d-8255-a69140f09f05
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[[(3S,6aR,6bS,8R,8aR,12aS,14bR)-8a-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(E)-3-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoyl]oxyoxan-2-yl]oxycarbonyl-8-hydroxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-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)O)O)C)C(=O)OC7C(C(C(CO7)O)O)OC(=O)C=CC8=CC(=C(C=C8)OC9C(C(C(C(O9)CO)O)O)O)OC)C
• SMILES (Isomeric): C[C@]12CC[C@@H](C(C1CC[C@@]3(C2CC=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](CO6)O)O)OC(=O)/C=C/C7=CC(=C(C=C7)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)OC)O)C)C)(C)C)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)C(=O)O)O)O)O
• InChI: InChI=1S/C57H82O22/c1-52(2)19-20-57(51(71)79-50-46(38(62)29(59)25-73-50)77-37(61)14-10-26-9-12-30(31(21-26)72-8)74-48-43(67)40(64)39(63)32(24-58)75-48)28(22-52)27-11-13-34-54(5)17-16-36(76-49-44(68)41(65)42(66)45(78-49)47(69)70)53(3,4)33(54)15-18-55(34,6)56(27,7)23-35(57)60/h9-12,14,21,28-29,32-36,38-46,48-50,58-60,62-68H,13,15-20,22-25H2,1-8H3,(H,69,70)/b14-10+/t28-,29-,32+,33?,34?,35+,36-,38-,39+,40-,41-,42-,43+,44+,45-,46+,48+,49+,50-,54-,55+,56+,57+/m0/s1
• InChI Key: VPRXKSGJJTXNTG-IILVBNMYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₇H₈₂O₂₂
• Molecular Weight: 1119.20 g/mol
• Exact Mass: 1118.52977424 g/mol
• Topological Polar Surface Area (TPSA): 348.00 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 1.47
• H-Bond Acceptor: 21
• H-Bond Donor: 11
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8680	86.80%
Caco-2	-	0.8636	86.36%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7598	75.98%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7032	70.32%
OATP1B3 inhibitior	-	0.2595	25.95%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.9489	94.89%
P-glycoprotein inhibitior	+	0.7451	74.51%
P-glycoprotein substrate	+	0.6018	60.18%
CYP3A4 substrate	+	0.7462	74.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8706	87.06%
CYP3A4 inhibition	-	0.7405	74.05%
CYP2C9 inhibition	-	0.8191	81.91%
CYP2C19 inhibition	-	0.8017	80.17%
CYP2D6 inhibition	-	0.9173	91.73%
CYP1A2 inhibition	-	0.7097	70.97%
CYP2C8 inhibition	+	0.8532	85.32%
CYP inhibitory promiscuity	-	0.9547	95.47%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6274	62.74%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.8982	89.82%
Skin irritation	-	0.7231	72.31%
Skin corrosion	-	0.9432	94.32%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7551	75.51%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.8834	88.34%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.9852	98.52%
Acute Oral Toxicity (c)	III	0.5612	56.12%
Estrogen receptor binding	+	0.7245	72.45%
Androgen receptor binding	+	0.7524	75.24%
Thyroid receptor binding	+	0.6669	66.69%
Glucocorticoid receptor binding	+	0.8036	80.36%
Aromatase binding	+	0.6617	66.17%
PPAR gamma	+	0.8267	82.67%
Honey bee toxicity	-	0.6457	64.57%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5555	55.55%
Fish aquatic toxicity	+	0.9815	98.15%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.12%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.64%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.94%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.49%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.22%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.73%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.34%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.09%	89.00%
CHEMBL4302	P08183	P-glycoprotein 1	90.83%	92.98%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.43%	96.21%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.83%	95.50%
CHEMBL5028	O14672	ADAM10	86.56%	97.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.48%	93.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.79%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	84.76%	91.49%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.70%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.52%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.23%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.81%	89.62%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.42%	92.94%
CHEMBL1937	Q92769	Histone deacetylase 2	83.36%	94.75%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.77%	97.14%
CHEMBL221	P23219	Cyclooxygenase-1	82.49%	90.17%
CHEMBL5255	O00206	Toll-like receptor 4	82.28%	92.50%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	82.04%	89.44%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.67%	91.07%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	80.49%	90.24%

Plants that contains it

• Tragopogon porrifolius
• Tragopogon pratensis

Cross-Links

• PubChem: 131752256
• LOTUS: LTS0178504
• wikiData: Q104401748