(1S,2R,5R,7S,10R,11R,15S,18S,20R,22R)-7-[(2R,3R,4S,5S,6R)-3-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,6,6,10,17,17-hexamethyl-18-(3,4,5-trimethoxybenzoyl)oxyhexacyclo[12.9.0.01,22.02,11.05,10.015,20]tricos-13-ene-20-carboxylic acid

Details

• Internal ID: 57060c94-a87a-49c6-a2f1-6081bea3116f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (1S,2R,5R,7S,10R,11R,15S,18S,20R,22R)-7-[(2R,3R,4S,5S,6R)-3-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,6,6,10,17,17-hexamethyl-18-(3,4,5-trimethoxybenzoyl)oxyhexacyclo[12.9.0.01,22.02,11.05,10.015,20]tricos-13-ene-20-carboxylic acid
• SMILES (Canonical): CC1(CC2C3=CCC4C5(CCC(C(C5CCC4(C36CC6CC2(CC1OC(=O)C7=CC(=C(C(=C7)OC)OC)OC)C(=O)O)C)(C)C)OC8C(C(C(C(O8)CO)O)O)OC9C(C(C(CO9)OC1C(C(C(CO1)O)O)O)O)O)C)C
• SMILES (Isomeric): C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]35C[C@@H]5C[C@@]6([C@H]4CC([C@H](C6)OC(=O)C7=CC(=C(C(=C7)OC)OC)OC)(C)C)C(=O)O)C)(C)C)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O[C@H]9[C@@H]([C@H]([C@@H](CO9)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)O)O
• InChI: InChI=1S/C56H82O21/c1-51(2)20-28-27-10-11-35-53(5)14-13-36(76-49-45(41(62)39(60)32(22-57)73-49)77-48-43(64)40(61)33(24-72-48)74-47-42(63)38(59)29(58)23-71-47)52(3,4)34(53)12-15-54(35,6)56(27)19-26(56)18-55(28,50(66)67)21-37(51)75-46(65)25-16-30(68-7)44(70-9)31(17-25)69-8/h10,16-17,26,28-29,32-43,45,47-49,57-64H,11-15,18-24H2,1-9H3,(H,66,67)/t26-,28-,29+,32+,33+,34-,35+,36-,37-,38-,39+,40-,41-,42+,43+,45+,47-,48-,49-,53-,54+,55+,56+/m0/s1
• InChI Key: GCZSPLWJXTWMPZ-GWSKRHMESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₆H₈₂O₂₁
• Molecular Weight: 1091.20 g/mol
• Exact Mass: 1090.53485962 g/mol
• Topological Polar Surface Area (TPSA): 309.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.46
• H-Bond Acceptor: 20
• H-Bond Donor: 9
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8755	87.55%
Caco-2	-	0.8636	86.36%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7062	70.62%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7510	75.10%
OATP1B3 inhibitior	+	0.7980	79.80%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.9849	98.49%
P-glycoprotein inhibitior	+	0.7472	74.72%
P-glycoprotein substrate	+	0.6350	63.50%
CYP3A4 substrate	+	0.7527	75.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8664	86.64%
CYP3A4 inhibition	-	0.7473	74.73%
CYP2C9 inhibition	-	0.7182	71.82%
CYP2C19 inhibition	-	0.7544	75.44%
CYP2D6 inhibition	-	0.9114	91.14%
CYP1A2 inhibition	-	0.7026	70.26%
CYP2C8 inhibition	+	0.8334	83.34%
CYP inhibitory promiscuity	-	0.9481	94.81%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6386	63.86%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.8987	89.87%
Skin irritation	-	0.7334	73.34%
Skin corrosion	-	0.9396	93.96%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7481	74.81%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	-	0.7768	77.68%
skin sensitisation	-	0.8663	86.63%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.9053	90.53%
Acute Oral Toxicity (c)	III	0.5112	51.12%
Estrogen receptor binding	+	0.7117	71.17%
Androgen receptor binding	+	0.7526	75.26%
Thyroid receptor binding	+	0.6547	65.47%
Glucocorticoid receptor binding	+	0.7779	77.79%
Aromatase binding	+	0.6734	67.34%
PPAR gamma	+	0.8131	81.31%
Honey bee toxicity	-	0.6363	63.63%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5955	59.55%
Fish aquatic toxicity	+	0.9834	98.34%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4302	P08183	P-glycoprotein 1	99.12%	92.98%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.85%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.07%	96.09%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	93.22%	95.17%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	93.17%	96.77%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.79%	96.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.74%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.71%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.48%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	90.41%	90.17%
CHEMBL4208	P20618	Proteasome component C5	89.01%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.81%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.20%	92.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.72%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	85.54%	91.19%
CHEMBL5028	O14672	ADAM10	85.16%	97.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.99%	100.00%
CHEMBL1255126	O15151	Protein Mdm4	84.91%	90.20%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.80%	89.00%
CHEMBL5255	O00206	Toll-like receptor 4	84.69%	92.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.23%	91.07%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.90%	95.83%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	83.72%	97.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.60%	97.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.53%	95.89%
CHEMBL1871	P10275	Androgen Receptor	81.92%	96.43%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.04%	95.56%

Plants that contains it

• Verbesina virginica

Cross-Links

• PubChem: 162895646
• LOTUS: LTS0068792
• wikiData: Q105006593