Ipomotaoside A

Details

• Internal ID: 0a8e3357-9ba1-4e68-9381-02399e6bb653
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Oligosaccharides
• IUPAC Name: [(2S,3R,4R,5R,6S)-6-[(2S,3S,4S,5R,6S)-4-decanoyloxy-5-hydroxy-2-methyl-6-[[(1R,3S,5S,6R,7R,8R,20S,22R,24R,25R,26S)-7,25,26-trihydroxy-5,24-dimethyl-10-oxo-20-pentyl-2,4,9,21,23-pentaoxatricyclo[20.4.0.03,8]hexacosan-6-yl]oxy]oxan-3-yl]oxy-4-hydroxy-2-methyl-5-[(E)-3-phenylprop-2-enoyl]oxyoxan-3-yl] dodecanoate
• SMILES (Canonical): CCCCCCCCCCCC(=O)OC1C(OC(C(C1O)OC(=O)C=CC2=CC=CC=C2)OC3C(OC(C(C3OC(=O)CCCCCCCCC)O)OC4C(OC5C(C4O)OC(=O)CCCCCCCCCC(OC6C(O5)C(C(C(O6)C)O)O)CCCCC)C)C)C
• SMILES (Isomeric): CCCCCCCCCCCC(=O)O[C@H]1[C@@H](O[C@H]([C@@H]([C@@H]1O)OC(=O)/C=C/C2=CC=CC=C2)O[C@H]3[C@@H](O[C@H]([C@@H]([C@@H]3OC(=O)CCCCCCCCC)O)O[C@H]4[C@@H](O[C@@H]5[C@@H]([C@@H]4O)OC(=O)CCCCCCCCC[C@@H](O[C@H]6[C@H](O5)[C@H]([C@H]([C@H](O6)C)O)O)CCCCC)C)C)C
• InChI: InChI=1S/C71H116O21/c1-8-11-14-16-18-19-23-27-34-41-52(72)86-61-47(5)83-70(66(58(61)78)89-55(75)45-44-50-37-31-29-32-38-50)91-63-49(7)82-68(60(80)64(63)87-53(73)42-35-26-21-17-15-12-9-2)90-62-48(6)84-71-67(59(62)79)88-54(74)43-36-28-24-20-22-25-33-40-51(39-30-13-10-3)85-69-65(92-71)57(77)56(76)46(4)81-69/h29,31-32,37-38,44-49,51,56-71,76-80H,8-28,30,33-36,39-43H2,1-7H3/b45-44+/t46-,47+,48+,49+,51+,56+,57+,58-,59-,60-,61+,62+,63+,64+,65-,66-,67-,68+,69+,70+,71+/m1/s1
• InChI Key: RWELBFDBNJXLOK-RQSNGXSLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₇₁H₁₁₆O₂₁
• Molecular Weight: 1305.70 g/mol
• Exact Mass: 1304.80091070 g/mol
• Topological Polar Surface Area (TPSA): 280.00 Ų
• XlogP: 14.70
• Atomic LogP (AlogP): 10.84
• H-Bond Acceptor: 21
• H-Bond Donor: 5
• Rotatable Bonds: 31

Synonyms

• CHEMBL1631409
• CHEBI:70318
• BDBM50332939
• Q27138660
• (S)-jalapinolic acid 11-O-(2-O-trans-cinnamoyl)-[(4-O-n-dodecanoyl)]-alpha-L-rhamnopyranosyl-(1->4)-O-(3-O-n-decanoyl)-alpha-L-rhamnopyranosyl-(1->4)-O-alpha-L-rhamnopyranosyl-(1->2)-O-beta-D-fucopyranoside 1,2'''' ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8253	82.53%
Caco-2	-	0.8615	86.15%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.5569	55.69%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8029	80.29%
OATP1B3 inhibitior	-	0.3325	33.25%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.9762	97.62%
P-glycoprotein inhibitior	+	0.7432	74.32%
P-glycoprotein substrate	+	0.7202	72.02%
CYP3A4 substrate	+	0.7101	71.01%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8831	88.31%
CYP3A4 inhibition	-	0.6392	63.92%
CYP2C9 inhibition	-	0.9296	92.96%
CYP2C19 inhibition	-	0.7788	77.88%
CYP2D6 inhibition	-	0.9376	93.76%
CYP1A2 inhibition	-	0.8516	85.16%
CYP2C8 inhibition	+	0.8020	80.20%
CYP inhibitory promiscuity	-	0.9497	94.97%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6891	68.91%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.8988	89.88%
Skin irritation	-	0.7113	71.13%
Skin corrosion	-	0.9401	94.01%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7716	77.16%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.8787	87.87%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.9625	96.25%
Acute Oral Toxicity (c)	III	0.5778	57.78%
Estrogen receptor binding	+	0.8088	80.88%
Androgen receptor binding	+	0.6191	61.91%
Thyroid receptor binding	+	0.5845	58.45%
Glucocorticoid receptor binding	+	0.7455	74.55%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7994	79.94%
Honey bee toxicity	-	0.7663	76.63%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.6216	62.16%
Fish aquatic toxicity	+	0.9934	99.34%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.17%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.64%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.00%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.01%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.38%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.78%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.55%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.46%	89.00%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	90.47%	83.00%
CHEMBL5255	O00206	Toll-like receptor 4	90.14%	92.50%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	89.57%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.94%	93.56%
CHEMBL5805	Q9NR97	Toll-like receptor 8	86.81%	96.25%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	86.57%	93.00%
CHEMBL3401	O75469	Pregnane X receptor	86.16%	94.73%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	85.99%	91.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.87%	97.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.80%	92.62%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	85.53%	92.08%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.84%	99.23%
CHEMBL221	P23219	Cyclooxygenase-1	83.90%	90.17%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.83%	97.36%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.73%	100.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.63%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.12%	95.89%
CHEMBL3524	P56524	Histone deacetylase 4	81.84%	92.97%
CHEMBL5028	O14672	ADAM10	80.36%	97.50%

Plants that contains it

• Ipomoea batatas

Cross-Links

• PubChem: 50900934
• LOTUS: LTS0271758
• wikiData: Q27138660