Chrysanthellin A

Details

• Internal ID: ee8eab4d-a4d5-47ce-b9be-0bf3d2002b6b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [3-[5-[3,5-dihydroxy-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl] 5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(COC(C2O)OC3C(OC(C(C3O)O)OC4C(C(COC4OC(=O)C56CCC(CC5C7=CCC8C9(CCC(C(C9CCC8(C7(CC6O)C)C)(C)C)OC1C(C(C(C(O1)CO)O)O)O)C)(C)C)O)O)C)O)O)O)O
• SMILES (Isomeric): CC1C(C(C(C(O1)OC2C(COC(C2O)OC3C(OC(C(C3O)O)OC4C(C(COC4OC(=O)C56CCC(CC5C7=CCC8C9(CCC(C(C9CCC8(C7(CC6O)C)C)(C)C)OC1C(C(C(C(O1)CO)O)O)O)C)(C)C)O)O)C)O)O)O)O
• InChI: InChI=1S/C58H94O25/c1-23-34(63)37(66)40(69)48(76-23)81-45-28(61)22-74-47(43(45)72)80-44-24(2)77-49(42(71)39(44)68)82-46-35(64)27(60)21-75-51(46)83-52(73)58-17-16-53(3,4)18-26(58)25-10-11-31-55(7)14-13-33(79-50-41(70)38(67)36(65)29(20-59)78-50)54(5,6)30(55)12-15-56(31,8)57(25,9)19-32(58)62/h10,23-24,26-51,59-72H,11-22H2,1-9H3
• InChI Key: IBEZGTWSSFFKNB-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₈H₉₄O₂₅
• Molecular Weight: 1191.30 g/mol
• Exact Mass: 1190.60841848 g/mol
• Topological Polar Surface Area (TPSA): 393.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -1.91
• H-Bond Acceptor: 25
• H-Bond Donor: 14
• Rotatable Bonds: 11

Synonyms

• [3-[5-[3,5-dihydroxy-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl] 5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• (3-(5-(3,5-dihydroxy-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl)oxy-3,4-dihydroxy-6-methyloxan-2-yl)oxy-4,5-dihydroxyoxan-2-yl) 5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-(3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• RefChem:1081551
• 73039-13-1
• Chrysantellin A
• MFCD00075717
• EINECS 277-245-7
• C58H94O25
• orb1942045
• orb1992303
• SCHEMBL29558957
• IBEZGTWSSFFKNB-UHFFFAOYSA-N
• DTXSID801098866
• AKOS040734448
• FC65735
• DA-62304
• O-6-Deoxy-alpha-L-mannopyranosyl-(1a3)-O-beta-D-xylopyranosyl-(1a4)-O-6-deoxy-alpha-L-mannopyranosyl-(1a2)-alpha-D-xylopyranosyl (3beta,16alpha)-3-(beta-D-glucopyranosyloxy)-16-hydroxyolean-12-en-28-oate
• Olean-12-en-28-oic acid, 3-(beta-D-glucopyranosyloxy)-16-hydroxy-, O-6-deoxy-alpha-L-mannopyranosyl-(1-3)-O-beta-D-xylopyranosyl-(1-4)-O-6-deoxy-alpha-L-mannopyranosyl-(1-2)-alpha-D-xylopyranosyl ester, (3beta,16alpha)-
• Olean-12-en-28-oic acid, 3-(beta-D-glucopyranosyloxy)-16-hydroxy-,O-6-deoxy-alpha-l-mannopyranosyl-(1.3)-O-beta-D-xylopyranosyl-(1. 4)-O-6-deoxy-alpha-l-mannopyranosyl-(1.2)-alpha-D-xylopyranosyl ester, (3beta,16alpha)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7891	78.91%
Caco-2	-	0.8787	87.87%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8567	85.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.7738	77.38%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.9410	94.10%
P-glycoprotein inhibitior	+	0.7459	74.59%
P-glycoprotein substrate	-	0.5255	52.55%
CYP3A4 substrate	+	0.7409	74.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8587	85.87%
CYP3A4 inhibition	-	0.9300	93.00%
CYP2C9 inhibition	-	0.8838	88.38%
CYP2C19 inhibition	-	0.9101	91.01%
CYP2D6 inhibition	-	0.9422	94.22%
CYP1A2 inhibition	-	0.8933	89.33%
CYP2C8 inhibition	+	0.7294	72.94%
CYP inhibitory promiscuity	-	0.9668	96.68%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6254	62.54%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.8995	89.95%
Skin irritation	-	0.6103	61.03%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7638	76.38%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.9500	95.00%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.9521	95.21%
Acute Oral Toxicity (c)	III	0.7945	79.45%
Estrogen receptor binding	+	0.8058	80.58%
Androgen receptor binding	+	0.7359	73.59%
Thyroid receptor binding	+	0.6088	60.88%
Glucocorticoid receptor binding	+	0.8002	80.02%
Aromatase binding	+	0.6587	65.87%
PPAR gamma	+	0.8403	84.03%
Honey bee toxicity	-	0.6557	65.57%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5195	51.95%
Fish aquatic toxicity	+	0.9411	94.11%

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	98.04%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.96%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	92.23%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.89%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.26%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.47%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.84%	89.00%
CHEMBL1937	Q92769	Histone deacetylase 2	86.76%	94.75%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.62%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.96%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.32%	100.00%
CHEMBL2581	P07339	Cathepsin D	84.95%	98.95%
CHEMBL5028	O14672	ADAM10	84.63%	97.50%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.19%	96.77%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.98%	94.00%
CHEMBL226	P30542	Adenosine A1 receptor	83.61%	95.93%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.70%	96.21%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	81.81%	89.44%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.78%	96.61%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.82%	86.92%

Plants that contains it

• Chrysanthellum americanum

Cross-Links

• PubChem: 156099
• LOTUS: LTS0174797
• wikiData: Q105036474