[(2S,3R,4S,5R,6S)-5-[(Z)-but-2-enoyl]oxy-4-hydroxy-6-methyl-2-[[(1S,3S,5R,6R,7S,8R,20S,22R,24R,25S,26S,27R,29S,31R,32R,33R)-6,25,26,32-tetrahydroxy-5,31-bis(hydroxymethyl)-24-methyl-7-[(2S)-2-methylbutanoyl]oxy-10-oxo-20-pentyl-2,4,9,21,23,28,30-heptaoxatetracyclo[27.3.1.03,8.022,27]tritriacontan-33-yl]oxy]oxan-3-yl] (2S,3R)-3-hydroxy-2-methylbutanoate

Details

• Internal ID: 371a3e98-89af-4ee8-a773-343cc08b9f41
• Taxonomy: Lipids and lipid-like molecules > Saccharolipids
• IUPAC Name: [(2S,3R,4S,5R,6S)-5-[(Z)-but-2-enoyl]oxy-4-hydroxy-6-methyl-2-[[(1S,3S,5R,6R,7S,8R,20S,22R,24R,25S,26S,27R,29S,31R,32R,33R)-6,25,26,32-tetrahydroxy-5,31-bis(hydroxymethyl)-24-methyl-7-[(2S)-2-methylbutanoyl]oxy-10-oxo-20-pentyl-2,4,9,21,23,28,30-heptaoxatetracyclo[27.3.1.03,8.022,27]tritriacontan-33-yl]oxy]oxan-3-yl] (2S,3R)-3-hydroxy-2-methylbutanoate
• SMILES (Canonical): CCCCCC1CCCCCCCCCC(=O)OC2C(C(C(OC2OC3C(C(OC(C3OC4C(C(C(C(O4)C)OC(=O)C=CC)O)OC(=O)C(C)C(C)O)OC5C(C(C(OC5O1)C)O)O)CO)O)CO)O)OC(=O)C(C)CC
• SMILES (Isomeric): CCCCC[C@H]1CCCCCCCCCC(=O)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2O[C@H]3[C@@H]([C@H](O[C@H]([C@@H]3O[C@H]4[C@@H]([C@H]([C@H]([C@@H](O4)C)OC(=O)/C=C\C)O)OC(=O)[C@@H](C)[C@@H](C)O)O[C@@H]5[C@H]([C@@H]([C@H](O[C@H]5O1)C)O)O)CO)O)CO)O)OC(=O)[C@@H](C)CC
• InChI: InChI=1S/C54H90O24/c1-9-12-18-22-32-23-19-16-14-13-15-17-20-24-36(59)73-47-43(74-49(65)27(4)11-3)38(61)33(25-55)70-53(47)76-44-39(62)34(26-56)71-54(77-45-40(63)37(60)30(7)67-51(45)69-32)48(44)78-52-46(75-50(66)28(5)29(6)57)41(64)42(31(8)68-52)72-35(58)21-10-2/h10,21,27-34,37-48,51-57,60-64H,9,11-20,22-26H2,1-8H3/b21-10-/t27-,28-,29+,30+,31-,32-,33+,34+,37+,38+,39+,40-,41-,42-,43-,44-,45+,46+,47+,48+,51-,52-,53-,54-/m0/s1
• InChI Key: BNPHLFJALDKJDF-RHBIIKFKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₉₀O₂₄
• Molecular Weight: 1123.30 g/mol
• Exact Mass: 1122.58220373 g/mol
• Topological Polar Surface Area (TPSA): 341.00 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 1.65
• H-Bond Acceptor: 24
• H-Bond Donor: 8
• Rotatable Bonds: 16

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4854	48.54%
Caco-2	-	0.8690	86.90%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.7754	77.54%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8033	80.33%
OATP1B3 inhibitior	+	0.8327	83.27%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.8872	88.72%
P-glycoprotein inhibitior	+	0.7168	71.68%
P-glycoprotein substrate	+	0.7444	74.44%
CYP3A4 substrate	+	0.7180	71.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8972	89.72%
CYP3A4 inhibition	-	0.6983	69.83%
CYP2C9 inhibition	-	0.9356	93.56%
CYP2C19 inhibition	-	0.8352	83.52%
CYP2D6 inhibition	-	0.9419	94.19%
CYP1A2 inhibition	-	0.8954	89.54%
CYP2C8 inhibition	+	0.7225	72.25%
CYP inhibitory promiscuity	-	0.9710	97.10%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7223	72.23%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9040	90.40%
Skin irritation	-	0.7695	76.95%
Skin corrosion	-	0.9587	95.87%
Ames mutagenesis	-	0.7178	71.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.6641	66.41%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.9310	93.10%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	-	0.6000	60.00%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.8877	88.77%
Acute Oral Toxicity (c)	III	0.6432	64.32%
Estrogen receptor binding	+	0.8272	82.72%
Androgen receptor binding	+	0.6557	65.57%
Thyroid receptor binding	+	0.5351	53.51%
Glucocorticoid receptor binding	+	0.6936	69.36%
Aromatase binding	+	0.6139	61.39%
PPAR gamma	+	0.7524	75.24%
Honey bee toxicity	-	0.7000	70.00%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5427	54.27%
Fish aquatic toxicity	+	0.9528	95.28%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.63%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.70%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.15%	91.11%
CHEMBL4072	P07858	Cathepsin B	95.24%	93.67%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	93.84%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	92.61%	92.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.61%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.68%	97.25%
CHEMBL3359	P21462	Formyl peptide receptor 1	91.19%	93.56%
CHEMBL340	P08684	Cytochrome P450 3A4	90.68%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.28%	99.17%
CHEMBL5255	O00206	Toll-like receptor 4	89.36%	92.50%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	89.10%	97.29%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	88.86%	92.88%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	87.77%	95.64%
CHEMBL2996	Q05655	Protein kinase C delta	87.50%	97.79%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.32%	94.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.30%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.05%	97.09%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	86.93%	98.75%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.08%	96.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.68%	95.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.04%	94.45%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	84.19%	91.81%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	84.00%	83.00%
CHEMBL3401	O75469	Pregnane X receptor	83.88%	94.73%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	82.69%	97.47%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.49%	95.83%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	82.44%	96.37%
CHEMBL2514	O95665	Neurotensin receptor 2	82.42%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.39%	95.89%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.39%	96.47%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.05%	96.61%
CHEMBL4462	Q8IXJ6	NAD-dependent deacetylase sirtuin 2	81.56%	90.24%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.32%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.30%	86.33%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.26%	100.00%
CHEMBL5203	P33316	dUTP pyrophosphatase	80.75%	99.18%

Plants that contains it

• Calystegia soldanella

Cross-Links

• PubChem: 162973449
• LOTUS: LTS0268593
• wikiData: Q104664608