Fumonisin B1

Details

• Internal ID: 3217f5d2-05d2-4c30-bd25-e11332f82d68
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Fumonisins
• IUPAC Name: (2R)-2-[2-[(5R,6R,7S,9S,11R,16R,18S,19S)-19-amino-6-[(3R)-3,4-dicarboxybutanoyl]oxy-11,16,18-trihydroxy-5,9-dimethylicosan-7-yl]oxy-2-oxoethyl]butanedioic acid
• InChI: InChI=1S/C34H59NO15/c1-5-6-9-20(3)32(50-31(44)17-23(34(47)48)15-29(41)42)27(49-30(43)16-22(33(45)46)14-28(39)40)13-19(2)12-24(36)10-7-8-11-25(37)18-26(38)21(4)35/h19-27,32,36-38H,5-18,35H2,1-4H3,(H,39,40)(H,41,42)(H,45,46)(H,47,48)/t19-,20+,21-,22+,23+,24+,25+,26-,27-,32+/m0/s1
• InChI Key: UVBUBMSSQKOIBE-DSLOAKGESA-N
• Popularity: 3,136 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₅₉NO₁₅
• Molecular Weight: 721.80 g/mol
• Exact Mass: 721.38847018 g/mol
• Topological Polar Surface Area (TPSA): 289.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): 2.56
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 29

Synonyms

• Macrofusine
• 116355-83-0
• fumonisin-B1
• fumonisin B(1)
• 3ZZM97XZ32
• DTXSID6020644
• CHEBI:38221
• NSC-629151
• 1,2,3-Propanetricarboxylic acid, 1,1'-(1-(12-amino-4,9,11-trihydroxy-2-methyltridecyl)-2-(1-methylpentyl)-1,2-ethanediyl) ester
• 1,2,3-Propanetricarboxylic acid, 1,1'-[(1S,2R)-1-[(2S,4R,9R,11S,12S)-12-amino-4,9,11-trihydroxy-2-methyltridecyl]-2-[(1R)-1-methylpentyl]-1,2-ethanediyl] ester, (2R,2'R)-
• (2R)-2-[2-[(5R,6R,7S,9S,11R,16R,18S,19S)-19-amino-6-[(3R)-3,4-dicarboxybutanoyl]oxy-11,16,18-trihydroxy-5,9-dimethylicosan-7-yl]oxy-2-oxoethyl]butanedioic acid
• (2R,2'R)-2,2'-{[(5R,6R,7S,9S,11R,16R,18S,19S)-19-amino-11,16,18-trihydroxy-5,9-dimethylicosane-6,7-diyl]bis[oxy(2-oxoethane-2,1-diyl)]}dibutanedioic acid
• (2R)-2-(2-((5R,6R,7S,9S,11R,16R,18S,19S)-19-amino-6-((3R)-3,4-dicarboxybutanoyl)oxy-11,16,18-trihydroxy-5,9-dimethylicosan-7-yl)oxy-2-oxoethyl)butanedioic acid
• (2R,2'R)-2,2'-(((5R,6R,7S,9S,11R,16R,18S,19S)-19-amino-11,16,18-trihydroxy-5,9-dimethylicosane-6,7-diyl)bis(oxy(2-oxoethane-2,1-diyl)))dibutanedioic acid
• RefChem:141697
• GlyTouCan:G93479DK
• 1,2,3-PROPANETRICARBOXYLIC ACID, 1,1'-((1S,2R)-1-((2S,4R,9R,11S,12S)-12-AMINO-4,9,11-TRIHYDROXY-2-METHYLTRIDECYL)-2-((1R)-1-METHYLPENTYL)-1,2-ETHANEDIYL) ESTER, (2R,2'R)-
• DTXCID201527025
• 2-(2-((19-amino-6-((3,4-dicarboxybutanoyl)oxy)-11,16,18-trihydroxy-5,9-dimethylicosan-7-yl)oxy)-2-oxoethyl)butanedioic acid
• 2-(2-(19-amino-6-(3,4-dicarboxybutanoyloxy)-11,16,18-trihydroxy-5,9-dimethylicosan-7-yl)oxy-2-oxoethyl)butanedioic acid
• G93479DK
• 621-436-3
• NSC629151
• FB1
• Fumonisin B1 50 microg/mL in Acetonitrile/Water
• (R)-3-Carboxy-pentanedioic acid mono-{(1S,3S,5R,10R,12S,13S)-13-amino-1-[(1R,2R)-1-((R)-3,4-dicarboxy-butyryloxy)-2-methyl-hexyl]-5,10,12-trihydroxy-3-methyl-tetradecyl} ester
• UNII-3ZZM97XZ32
• CCRIS 4433
• HSDB 7077
• UVBUBMSSQKOIBE-DSLOAKGESA-N
• 1,2,3-Propanetricarboxylic acid, 1,1'-[1-(12-amino-4,9,11-trihydroxy-2-methyltridecyl)-2-(1-methylpentyl)-1,2-ethanediyl] ester, [2S-[1[1R*(S*),2S*(S*),2(S*)],2R*,4S*,9S*,11R*,12R*]]-; Fumonisin B1
• NSC 629151
• FUMONISIN B1 [MI]
• A1D5V
• FUMONISIN B1 [IARC]
• CHEMBL5282242
• SCHEMBL13555629
• Fumonisin B1, reference material
• MSK7224
• 19 - Fusarium mycotoxins in oats
• GLXC-25523
• EX-A8017
• HY-N6719
• LMSP01080022
• MSK7224-100M
• AKOS024457430
• FF23618
• DA-53128
• CS-0029116
• Fumonisin B1 solution in Methanol, 100ug/mL
• G14340
• Q63395324
• Fumonisin B1 from Fusarium moniliforme, >=98% (HPLC)
• (2R)-2-[2-[(1S,3S,5R,10R,12S,13S)-13-amino-1-[(1R,2R)-1-[(3R)-3,4-dicarboxybutanoyl]oxy-2-methyl-hexyl]-5,10,12-trihydroxy-3-methyl-tetradecoxy]-2-oxo-ethyl]butanedioic acid
• (2R,2'R)-1,2,3-Propanetricarboxylic acid 1,1'-[(1S,2R)-1-[(2S,4R,9R,11S,12S)-12-amino-4,9,11-trihydroxy-2-methyltridecyl]-2-[(1R)-1- methylpentyl]-1,2-ethanediyl] ester
• 1,2,3-Propanetricarboxylic acid, 1,1'-(1-(12-amino-4,9,11-trihydroxy-2-methyltridecyl)-2-(1-methylpentyl)-1,2-ethanediyl)ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6536	65.36%
Caco-2	-	0.8543	85.43%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5542	55.42%
OATP2B1 inhibitior	-	0.5665	56.65%
OATP1B1 inhibitior	+	0.8889	88.89%
OATP1B3 inhibitior	+	0.9267	92.67%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7232	72.32%
P-glycoprotein inhibitior	+	0.7043	70.43%
P-glycoprotein substrate	-	0.8575	85.75%
CYP3A4 substrate	+	0.5944	59.44%
CYP2C9 substrate	-	0.5982	59.82%
CYP2D6 substrate	-	0.7891	78.91%
CYP3A4 inhibition	-	0.6368	63.68%
CYP2C9 inhibition	-	0.8342	83.42%
CYP2C19 inhibition	-	0.7989	79.89%
CYP2D6 inhibition	-	0.8325	83.25%
CYP1A2 inhibition	-	0.5945	59.45%
CYP2C8 inhibition	-	0.7225	72.25%
CYP inhibitory promiscuity	-	0.9392	93.92%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.6442	64.42%
Eye corrosion	-	0.9784	97.84%
Eye irritation	-	0.9024	90.24%
Skin irritation	-	0.8659	86.59%
Skin corrosion	-	0.9528	95.28%
Ames mutagenesis	-	1.0000	100.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3837	38.37%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8963	89.63%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	-	0.7566	75.66%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	+	0.6312	63.12%
Acute Oral Toxicity (c)	III	0.6849	68.49%
Estrogen receptor binding	+	0.8078	80.78%
Androgen receptor binding	+	0.6996	69.96%
Thyroid receptor binding	-	0.5472	54.72%
Glucocorticoid receptor binding	+	0.6562	65.62%
Aromatase binding	+	0.5887	58.87%
PPAR gamma	+	0.5774	57.74%
Honey bee toxicity	-	0.8849	88.49%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.7697	76.97%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	98.79%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.50%	96.09%
CHEMBL2581	P07339	Cathepsin D	98.43%	98.95%
CHEMBL236	P41143	Delta opioid receptor	96.38%	99.35%
CHEMBL1907	P15144	Aminopeptidase N	96.23%	93.31%
CHEMBL3359	P21462	Formyl peptide receptor 1	94.15%	93.56%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	92.96%	97.29%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.95%	99.17%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	91.83%	97.21%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	91.77%	96.95%
CHEMBL4040	P28482	MAP kinase ERK2	91.73%	83.82%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	91.26%	96.47%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.10%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.09%	91.11%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	86.95%	94.08%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	85.63%	100.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.52%	90.71%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	85.37%	92.86%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	85.29%	96.00%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	84.71%	100.00%
CHEMBL3776	Q14790	Caspase-8	83.81%	97.06%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.25%	95.50%
CHEMBL1255126	O15151	Protein Mdm4	81.79%	90.20%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.97%	94.45%
CHEMBL2514	O95665	Neurotensin receptor 2	80.89%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.74%	97.25%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 2733487
• LOTUS: LTS0119293
• wikiData: Q63395324