[(1S,3S,4R,5S,6S,8S,10S,16S,23S,24R,25R,26R)-16-acetyloxy-4,5,26-trihydroxy-6-methyl-17,20-dioxo-24-[(E)-3-phenylprop-2-enoyl]oxy-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.03,8]heptacosan-25-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: 5bcb235b-c728-4486-bf55-df77ce257d9e
• Taxonomy: Lipids and lipid-like molecules > Saccharolipids
• IUPAC Name: [(1S,3S,4R,5S,6S,8S,10S,16S,23S,24R,25R,26R)-16-acetyloxy-4,5,26-trihydroxy-6-methyl-17,20-dioxo-24-[(E)-3-phenylprop-2-enoyl]oxy-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.03,8]heptacosan-25-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CCCC1CCCCCC(C(=O)CCC(=O)OCC2C(C(C(C(O2)OC3C(C(C(OC3O1)C)O)O)O)OC(=O)C(=CC)C)OC(=O)C=CC4=CC=CC=C4)OC(=O)C
• SMILES (Isomeric): CCC[C@H]1CCCCC[C@@H](C(=O)CCC(=O)OC[C@H]2[C@H]([C@@H]([C@H]([C@@H](O2)O[C@H]3[C@@H]([C@@H]([C@@H](O[C@@H]3O1)C)O)O)O)OC(=O)/C(=C\C)/C)OC(=O)/C=C/C4=CC=CC=C4)OC(=O)C
• InChI: InChI=1S/C42H58O16/c1-6-14-28-17-12-9-13-18-30(53-26(5)43)29(44)20-22-32(45)51-23-31-37(56-33(46)21-19-27-15-10-8-11-16-27)38(57-40(50)24(3)7-2)36(49)41(55-31)58-39-35(48)34(47)25(4)52-42(39)54-28/h7-8,10-11,15-16,19,21,25,28,30-31,34-39,41-42,47-49H,6,9,12-14,17-18,20,22-23H2,1-5H3/b21-19+,24-7-/t25-,28-,30-,31-,34+,35+,36+,37+,38+,39-,41-,42+/m0/s1
• InChI Key: ZGJXOLWJZBARNR-IVHKYEQMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₅₈O₁₆
• Molecular Weight: 818.90 g/mol
• Exact Mass: 818.37248576 g/mol
• Topological Polar Surface Area (TPSA): 220.00 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 3.40
• H-Bond Acceptor: 16
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8137	81.37%
Caco-2	-	0.8669	86.69%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8311	83.11%
OATP2B1 inhibitior	-	0.5755	57.55%
OATP1B1 inhibitior	+	0.8123	81.23%
OATP1B3 inhibitior	+	0.8638	86.38%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.9719	97.19%
P-glycoprotein inhibitior	+	0.7566	75.66%
P-glycoprotein substrate	+	0.7234	72.34%
CYP3A4 substrate	+	0.6908	69.08%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8872	88.72%
CYP3A4 inhibition	-	0.5628	56.28%
CYP2C9 inhibition	-	0.8467	84.67%
CYP2C19 inhibition	-	0.6489	64.89%
CYP2D6 inhibition	-	0.9069	90.69%
CYP1A2 inhibition	-	0.6978	69.78%
CYP2C8 inhibition	+	0.7657	76.57%
CYP inhibitory promiscuity	-	0.8773	87.73%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6300	63.00%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.9181	91.81%
Skin irritation	-	0.7575	75.75%
Skin corrosion	-	0.9692	96.92%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7393	73.93%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.8567	85.67%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.8727	87.27%
Acute Oral Toxicity (c)	III	0.6872	68.72%
Estrogen receptor binding	+	0.8359	83.59%
Androgen receptor binding	+	0.5800	58.00%
Thyroid receptor binding	+	0.5161	51.61%
Glucocorticoid receptor binding	+	0.7221	72.21%
Aromatase binding	+	0.5221	52.21%
PPAR gamma	+	0.7480	74.80%
Honey bee toxicity	-	0.7347	73.47%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9890	98.90%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.73%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.31%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.07%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.13%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.30%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.47%	96.00%
CHEMBL221	P23219	Cyclooxygenase-1	94.30%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.26%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.81%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	87.69%	94.73%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	87.28%	83.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	86.79%	91.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.75%	99.23%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.75%	93.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.72%	92.62%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.67%	93.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.78%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.19%	95.89%

Plants that contains it

• Eupatorium japonicum
• Helianthus annuus
• Helianthus gracilentus
• Helianthus maximiliani
• Helianthus resinosus
• Ipomoea squamosa
• Ophryosporus lorentzii
• Perityle emoryi
• Tithonia rotundifolia

Cross-Links

• PubChem: 102397824
• LOTUS: LTS0099523
• wikiData: Q105386237