(1S,2R,5R,7S,10R,11R,15S,18S,20R,22S)-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-[(E)-3-phenylprop-2-enoyl]oxyhexacyclo[12.9.0.01,22.02,11.05,10.015,20]tricos-13-ene-20-carboxylic acid

Details

• Internal ID: 1d2f9aa9-201d-4d99-80a2-a7463802a89e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (1S,2R,5R,7S,10R,11R,15S,18S,20R,22S)-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-[(E)-3-phenylprop-2-enoyl]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)C=CC7=CC=CC=C7)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)/C=C/C7=CC=CC=C7)(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/C55H78O18/c1-50(2)22-30-29-13-14-35-52(5)18-17-36(72-48-45(42(62)40(60)32(24-56)69-48)73-47-44(64)41(61)33(26-68-47)70-46-43(63)39(59)31(57)25-67-46)51(3,4)34(52)16-19-53(35,6)55(29)21-28(55)20-54(30,49(65)66)23-37(50)71-38(58)15-12-27-10-8-7-9-11-27/h7-13,15,28,30-37,39-48,56-57,59-64H,14,16-26H2,1-6H3,(H,65,66)/b15-12+/t28-,30+,31-,32-,33-,34+,35-,36+,37+,39+,40-,41+,42+,43-,44-,45-,46+,47+,48+,52+,53-,54-,55-/m1/s1
• InChI Key: NDCPZFPNVULXLE-XQDROYBISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₅H₇₈O₁₈
• Molecular Weight: 1027.20 g/mol
• Exact Mass: 1026.51881563 g/mol
• Topological Polar Surface Area (TPSA): 281.00 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 2.83
• H-Bond Acceptor: 17
• H-Bond Donor: 9
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8153	81.53%
Caco-2	-	0.8685	86.85%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.8075	80.75%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7538	75.38%
OATP1B3 inhibitior	-	0.2898	28.98%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.9724	97.24%
P-glycoprotein inhibitior	+	0.7453	74.53%
P-glycoprotein substrate	+	0.6070	60.70%
CYP3A4 substrate	+	0.7500	75.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8779	87.79%
CYP3A4 inhibition	-	0.6621	66.21%
CYP2C9 inhibition	-	0.7238	72.38%
CYP2C19 inhibition	-	0.8481	84.81%
CYP2D6 inhibition	-	0.9284	92.84%
CYP1A2 inhibition	-	0.8121	81.21%
CYP2C8 inhibition	+	0.8415	84.15%
CYP inhibitory promiscuity	-	0.9502	95.02%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6281	62.81%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9006	90.06%
Skin irritation	-	0.6609	66.09%
Skin corrosion	-	0.9396	93.96%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7514	75.14%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.7234	72.34%
skin sensitisation	-	0.8771	87.71%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.8661	86.61%
Acute Oral Toxicity (c)	III	0.6747	67.47%
Estrogen receptor binding	+	0.7707	77.07%
Androgen receptor binding	+	0.7577	75.77%
Thyroid receptor binding	+	0.6105	61.05%
Glucocorticoid receptor binding	+	0.7532	75.32%
Aromatase binding	+	0.5910	59.10%
PPAR gamma	+	0.8086	80.86%
Honey bee toxicity	-	0.6388	63.88%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5155	51.55%
Fish aquatic toxicity	+	0.9842	98.42%

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	99.26%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	97.40%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.82%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.87%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.22%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.67%	95.56%
CHEMBL4302	P08183	P-glycoprotein 1	92.11%	92.98%
CHEMBL5028	O14672	ADAM10	91.20%	97.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.88%	89.00%
CHEMBL1937	Q92769	Histone deacetylase 2	87.69%	94.75%
CHEMBL2581	P07339	Cathepsin D	86.86%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.10%	95.89%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	86.08%	97.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.91%	96.00%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	85.50%	94.08%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.34%	95.83%
CHEMBL4208	P20618	Proteasome component C5	81.56%	90.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.42%	100.00%
CHEMBL2959	Q08881	Tyrosine-protein kinase ITK/TSK	81.27%	95.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.22%	91.07%

Plants that contains it

• Verbesina virginica

Cross-Links

• PubChem: 44178747
• LOTUS: LTS0033727
• wikiData: Q105177493