Molecule

Ochratoxin A

AlkaPlorer ID: AK012188

Synonym: None

IUPAC Name: (2S)-2-[[(3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydroisochromene-7-carbonyl]amino]-3-phenylpropanoic acid

Structure

SMILES: C[C@@H]1CC2=C(Cl)C=C(C(O)=N[C@@H](CC3=CC=CC=C3)C(=O)O)C(O)=C2C(=O)O1

InChI: InChI=1S/C20H18ClNO6/c1-10-7-12-14(21)9-13(17(23)16(12)20(27)28-10)18(24)22-15(19(25)26)8-11-5-3-2-4-6-11/h2-6,9-10,15,23H,7-8H2,1H3,(H,22,24)(H,25,26)/t10-,15+/m1/s1

InChIKey: RWQKHEORZBHNRI-BMIGLBTASA-N

Reference

Effects of brevianamide A, its photolysis product brevianamide D, and ochratoxin A from two Penicillium strains on the insect pests Spodoptera frugiperda and Heliothis virescens

PubChem CID: 442530

CAS: 303-47-9

LOTUS: LTS0068740

SuperNatural Ⅲ: SN0337200-04

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NPAtlas: NPA016066

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Aspergillus ochraceus	Aspergillus	Aspergillaceae	Eurotiales	Eurotiomycetes	Ascomycota	Fungi	Eukaryota

Properties Information

Molecule Weight: 403.81800000000015

TPSA？: 116.42

MolLogP？: 3.1475000000000013

Number of H-Donors: 3

Number of H-Acceptors: 5

RingCount: 3

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Electrophorus electricus	Acetylcholinesterase	Inhibition	-6.4	%	10.1016/j.bmc.2012.09.040
Equus caballus	Cholinesterase	Inhibition	8.75	%	10.1016/j.bmc.2012.09.040
Equus caballus	Ferritin light chain	Potency	25118.9	nM	None
Homo sapiens	15-hydroxyprostaglandin dehydrogenase [NAD+]	Potency	28183.8	nM	None
Homo sapiens	Aldehyde dehydrogenase 1A1	Potency	31622.8	nM	None
Homo sapiens	Alpha-galactosidase A	Potency	19952.6	nM	None
Homo sapiens	Alpha-galactosidase A	Potency	35481.3	nM	None
Homo sapiens	Androgen Receptor	Potency	12589.3	nM	None
Homo sapiens	Androgen Receptor	Potency	50118.7	nM	None
Homo sapiens	Beta-glucocerebrosidase	Potency	31622.8	nM	None
Homo sapiens	Bile acid receptor FXR	Potency	1412.5	nM	None
Homo sapiens	Bile acid receptor FXR	Potency	44668.4	nM	None
Homo sapiens	Canalicular multispecific organic anion transporter 1	Activity	nan	None	10.1046/j.1523-1755.2000.00007.x
Homo sapiens	Canalicular multispecific organic anion transporter 1	IC50	58000.0	nM	10.1046/j.1523-1755.2000.00007.x
Homo sapiens	Cellular tumor antigen p53	Potency	891.3	nM	None
Homo sapiens	Estrogen receptor alpha	Potency	31622.8	nM	None
Homo sapiens	Estrogen receptor alpha	Potency	44668.4	nM	None
Homo sapiens	Glucocorticoid receptor	Potency	891.3	nM	None
Homo sapiens	Glucocorticoid receptor	Potency	3162.3	nM	None
Homo sapiens	HepG2	Activity	nan	None	10.1016/j.bmc.2009.10.050
Homo sapiens	HepG2	EC50	60.0	nM	10.1016/j.bmc.2009.10.050
Homo sapiens	HepG2	IC50	300.0	nM	10.1016/j.bmc.2009.10.050
Homo sapiens	Lysosomal alpha-glucosidase	Potency	35481.3	nM	None
Homo sapiens	Nuclear factor erythroid 2-related factor 2	Potency	3437.6	nM	None
Homo sapiens	Nuclear factor erythroid 2-related factor 2	Potency	68589.6	nM	None
Homo sapiens	Nuclear factor NF-kappa-B p105 subunit	Potency	44668.4	nM	None
Homo sapiens	Peroxisome proliferator-activated receptor delta	Potency	39810.7	nM	None
Homo sapiens	Peroxisome proliferator-activated receptor delta	Potency	44668.4	nM	None
Homo sapiens	Peroxisome proliferator-activated receptor gamma	Potency	562.3	nM	None
Homo sapiens	Peroxisome proliferator-activated receptor gamma	Potency	1995.3	nM	None
Homo sapiens	Solute carrier family 22 member 11	Activity	nan	None	10.1074/jbc.275.6.4507
Homo sapiens	Solute carrier family 22 member 11	Km	22900.0	nM	10.1016/s0167-4889(02)00187-8
Homo sapiens	Solute carrier family 22 member 6	Km	420.0	nM	10.1016/s0024-3205(01)01296-6
Homo sapiens	Solute carrier family 22 member 8	Activity	nan	None	10.1124/mol.59.5.1277
Homo sapiens	Solute carrier family 22 member 8	Km	750.0	nM	10.1016/s0024-3205(01)01296-6
Homo sapiens	Thyroid hormone receptor beta-1	Potency	4466.8	nM	None
Homo sapiens	Thyroid hormone receptor beta-1	Potency	44668.4	nM	None
Homo sapiens	Vitamin D receptor	Potency	12589.3	nM	None
Homo sapiens	Vitamin D receptor	Potency	44668.4	nM	None
Mus musculus	Nuclear receptor ROR-gamma	Potency	15848.9	nM	None
Mus musculus	Nuclear receptor ROR-gamma	Potency	22387.2	nM	None
Mus musculus	Putative organic anion transporter 5	Km	2000.0	nM	10.1152/ajprenal.00012.2004
Mus musculus	Solute carrier family 22 member 20	Ki	48977.88	nM	10.1074/jbc.m703467200
Mus musculus	Solute carrier family 22 member 20	Ki	49000.0	nM	10.1074/jbc.m703467200
Mus musculus	Solute carrier family 22 member 20	Vmax	4.8	pmol/hr	10.1074/jbc.m703467200
Mus musculus	Solute carrier family 22 member 6	Ki	6200.0	nM	10.1074/jbc.m703467200
Mus musculus	Solute carrier family 22 member 6	Ki	6309.57	nM	10.1074/jbc.m703467200
Mus musculus	Solute carrier family 22 member 6	Vmax	12.0	pmol/hr	10.1074/jbc.m703467200
Mus musculus	Solute carrier family 22 member 7	Activity	nan	None	10.1124/mol.62.1.7
Mycobacterium tuberculosis	L-cysteine:1D-myo-inositol 2-amino-2-deoxy-alpha-D-glucopyranoside ligase	IC50	2500000.0	nM	10.1016/j.bmcl.2011.02.042
Rattus norvegicus	Inositol monophosphatase 1	Potency	17782.8	nM	None
Rattus norvegicus	Solute carrier family 22 member 6	Km	570.0	nM	None
Rattus norvegicus	Solute carrier family 22 member 6	Km	2100.0	nM	None
Rattus norvegicus	Solute carrier family 22 member 8	Km	739.0	nM	10.1074/jbc.274.19.13675
Rattus norvegicus	Solute carrier organic anion transporter family member 1A1	Km	16600.0	nM	None
Rattus norvegicus	Solute carrier organic anion transporter family member 1A1	Km	29000.0	nM	10.1152/ajpgi.1999.276.4.g1037
Rattus norvegicus	Solute carrier organic anion transporter family member 1A3	Activity	nan	None	None
Rattus norvegicus	Solute carrier organic anion transporter family member 1A3	Km	5600.0	nM	None
Rattus norvegicus	Solute carrier organic anion transporter family member 1A3	Km	16600.0	nM	None
None	Unchecked	Potency	6309.6	nM	None
None	Unchecked	Potency	19952.6	nM	None
None	Unchecked	Ratio pKi	-0.89	None	10.1074/jbc.m703467200

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT013001	C[C@@H]1Cc2c(Cl)cc(C(=O)N[C@@H](Cc3ccccc3)C(=O)O)c(O)c2C(=O)O1>>C[C@@H]1Cc2c(Cl)cc(C(=O)O)c(O)c2C(=O)O1	RXN-21094
AKRT013002	C[C@@H]1Cc2c(Cl)cc(C(=O)N[C@@H](Cc3ccccc3)C(=O)O)c(O)c2C(=O)O1>>N[C@@H](Cc1ccccc1)C(=O)O	RXN-21094
AKRT013003	C[C@@H]1Cc2ccc(C(=O)N[C@@H](Cc3ccccc3)C(=O)O)c(O)c2C(=O)O1>>C[C@@H]1Cc2c(Cl)cc(C(=O)N[C@@H](Cc3ccccc3)C(=O)O)c(O)c2C(=O)O1	RXN-21095