2-[2-[19-Acetamido-6-(3,4-dicarboxybutanoyloxy)-11,16,18-trihydroxy-5,9-dimethylicosan-7-yl]oxy-2-oxoethyl]butanedioic acid

Details

• Internal ID: 9556cd20-8a9e-4ca9-b38f-696215aac79f
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Fumonisins
• IUPAC Name: 2-[2-[19-acetamido-6-(3,4-dicarboxybutanoyloxy)-11,16,18-trihydroxy-5,9-dimethylicosan-7-yl]oxy-2-oxoethyl]butanedioic acid
• SMILES (Canonical): CCCCC(C)C(C(CC(C)CC(CCCCC(CC(C(C)NC(=O)C)O)O)O)OC(=O)CC(CC(=O)O)C(=O)O)OC(=O)CC(CC(=O)O)C(=O)O
• SMILES (Isomeric): CCCCC(C)C(C(CC(C)CC(CCCCC(CC(C(C)NC(=O)C)O)O)O)OC(=O)CC(CC(=O)O)C(=O)O)OC(=O)CC(CC(=O)O)C(=O)O
• InChI: InChI=1S/C36H61NO16/c1-6-7-10-21(3)34(53-33(47)18-25(36(50)51)16-31(44)45)29(52-32(46)17-24(35(48)49)15-30(42)43)14-20(2)13-26(39)11-8-9-12-27(40)19-28(41)22(4)37-23(5)38/h20-22,24-29,34,39-41H,6-19H2,1-5H3,(H,37,38)(H,42,43)(H,44,45)(H,48,49)(H,50,51)
• InChI Key: ADACAMXIRQREOB-UHFFFAOYSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₆₁NO₁₆
• Molecular Weight: 763.90 g/mol
• Exact Mass: 763.39903486 g/mol
• Topological Polar Surface Area (TPSA): 292.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.74
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 30

Synonyms

• 2-[2-[19-acetamido-6-(3,4-dicarboxybutanoyloxy)-11,16,18-trihydroxy-5,9-dimethylicosan-7-yl]oxy-2-oxoethyl]butanedioic acid
• (2R)-2-[2-[(5R,6R,7S,9S,11R,16S,18R,19R)-19-acetamido-6-[(3R)-3,4-dicarboxybutanoyl]oxy-11,16,18-trihydroxy-5,9-dimethylicosan-7-yl]oxy-2-oxoethyl]butanedioic acid
• 1,2,3-Propanetricarboxylic acid 1,1'-[1-[12-(acetylamino)-4,9,11-trihydroxy-2-methyltridecyl]-2-(1-methylpentyl)-1,2-ethanediyl] ester, 9CI

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5595	55.95%
Caco-2	-	0.8611	86.11%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7788	77.88%
OATP2B1 inhibitior	-	0.5736	57.36%
OATP1B1 inhibitior	+	0.8681	86.81%
OATP1B3 inhibitior	+	0.9226	92.26%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8572	85.72%
BSEP inhibitior	+	0.7960	79.60%
P-glycoprotein inhibitior	+	0.7279	72.79%
P-glycoprotein substrate	-	0.6504	65.04%
CYP3A4 substrate	+	0.6310	63.10%
CYP2C9 substrate	+	0.6107	61.07%
CYP2D6 substrate	-	0.8675	86.75%
CYP3A4 inhibition	-	0.6521	65.21%
CYP2C9 inhibition	-	0.7801	78.01%
CYP2C19 inhibition	-	0.7827	78.27%
CYP2D6 inhibition	-	0.8865	88.65%
CYP1A2 inhibition	-	0.7761	77.61%
CYP2C8 inhibition	-	0.7347	73.47%
CYP inhibitory promiscuity	-	0.8445	84.45%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6817	68.17%
Eye corrosion	-	0.9848	98.48%
Eye irritation	-	0.9029	90.29%
Skin irritation	-	0.8611	86.11%
Skin corrosion	-	0.9780	97.80%
Ames mutagenesis	-	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6488	64.88%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.5426	54.26%
skin sensitisation	-	0.9261	92.61%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	-	0.7180	71.80%
Mitochondrial toxicity	-	0.7875	78.75%
Nephrotoxicity	+	0.8489	84.89%
Acute Oral Toxicity (c)	III	0.7293	72.93%
Estrogen receptor binding	+	0.8107	81.07%
Androgen receptor binding	+	0.6922	69.22%
Thyroid receptor binding	-	0.5391	53.91%
Glucocorticoid receptor binding	+	0.7056	70.56%
Aromatase binding	+	0.6521	65.21%
PPAR gamma	+	0.6502	65.02%
Honey bee toxicity	-	0.8588	85.88%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.8009	80.09%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.75%	83.82%
CHEMBL2581	P07339	Cathepsin D	99.18%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	98.82%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.89%	96.09%
CHEMBL3359	P21462	Formyl peptide receptor 1	95.87%	93.56%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	95.05%	97.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.33%	99.17%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	91.64%	97.29%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.52%	91.11%
CHEMBL3776	Q14790	Caspase-8	90.89%	97.06%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	89.00%	96.47%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	88.17%	96.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.81%	100.00%
CHEMBL1255126	O15151	Protein Mdm4	87.31%	90.20%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.53%	96.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.18%	96.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.53%	85.14%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	85.20%	92.86%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.00%	95.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.07%	94.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.89%	94.45%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	83.82%	100.00%
CHEMBL3308	P55212	Caspase-6	83.66%	97.56%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.43%	96.90%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.96%	89.50%
CHEMBL1907	P15144	Aminopeptidase N	82.75%	93.31%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.31%	90.71%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	82.07%	98.75%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.77%	82.50%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	81.41%	92.29%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.95%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	80.64%	94.73%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	80.16%	94.08%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 14077781
• LOTUS: LTS0154629
• wikiData: Q103816001