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name Structure Reference Source Properties Activities Metabolism

12771-72-1

AlkaPlorer ID: AK038474

Synonym: 'Verruculogen', 'Verruculogen TR 1', 'TR 1 toxin'

IUPAC Name: (9S,14S,17S,23R,24S)-23,24-dihydroxy-5-methoxy-12,12-dimethyl-9-(2-methylprop-1-enyl)-10,11-dioxa-8,15,21-triazahexacyclo[12.10.1.02,7.08,25.015,23.017,21]pentacosa-1(25),2(7),3,5-tetraene-16,22-dione

Structure

SMILES: COC1=CC=C2C3=C4[C@H](CC(C)(C)OO[C@@H](C=C(C)C)N4C2=C1)N1C(=O)[C@@H]2CCCN2C(=O)[C@]1(O)[C@H]3O

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InChI: InChI=1S/C27H33N3O7/c1-14(2)11-20-29-18-12-15(35-5)8-9-16(18)21-22(29)19(13-26(3,4)37-36-20)30-24(32)17-7-6-10-28(17)25(33)27(30,34)23(21)31/h8-9,11-12,17,19-20,23,31,34H,6-7,10,13H2,1-5H3/t17-,19-,20-,23-,27+/m0/s1

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InChIKey: LRXYHMMJJCTUMY-KZXQSYCZSA-N

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Source

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

Properties Information

Molecule Weight: 511.57500000000033

TPSA？: 113.70000000000002

MolLogP？: 2.855100000000001

Number of H-Donors: 2

Number of H-Acceptors: 8

RingCount: 6

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Alternaria alternata Alternaria alternata MIC 6.25 ug.mL-1 10.1021/jf300146n
Alternaria solani Alternaria solani MIC 12.5 ug.mL-1 10.1021/jf300146n
Artemia salina Artemia salina LC50 15.8 ug.mL-1 10.1021/jf300146n
Botrytis cinerea Botrytis cinerea MIC 6.25 ug.mL-1 10.1021/jf300146n
Cavia porcellus Ileum Activity 7.0 % 10.1021/np50073a020
Cavia porcellus Ileum Activity 11.0 % 10.1021/np50073a020
Cavia porcellus Ileum Activity 14.0 % 10.1021/np50073a020
Cavia porcellus Ileum Activity 109.0 % 10.1021/np50073a020
Cavia porcellus Ileum Activity 123.0 % 10.1021/np50073a020
Cavia porcellus Ileum Activity 127.0 % 10.1021/np50073a020
Cavia porcellus Ileum Activity nan None 10.1021/np50073a020
Colletotrichum gloeosporioides Colletotrichum gloeosporioides MIC 6.25 ug.mL-1 10.1021/jf300146n
Electrophorus electricus Acetylcholinesterase Inhibition 1.5 % 10.1016/j.bmc.2012.09.040
Equus caballus Cholinesterase Inhibition 17.99 % 10.1016/j.bmc.2012.09.040
Fusarium graminearum Fusarium graminearum MIC 6.25 ug.mL-1 10.1021/jf300146n
Fusarium oxysporum f. sp. niveum Fusarium oxysporum f. sp. niveum MIC 12.5 ug.mL-1 10.1021/jf300146n
Fusarium oxysporum f. sp. vasinfectum Fusarium oxysporum f. sp. vasinfectum MIC 25.0 ug.mL-1 10.1021/jf300146n
Fusarium solani Fusarium solani MIC 50.0 ug.mL-1 10.1021/jf300146n
Homo sapiens Jurkat IC50 97000.0 nM 10.1016/j.bmc.2010.02.034
Homo sapiens K562 IC50 41000.0 nM 10.1021/np800700e
Homo sapiens KB Activity nan None 10.1021/np800700e
Homo sapiens MCF7 Activity nan None 10.1021/np800700e
Mus musculus Mus musculus Activity 0.78 mg kg-1 10.1016/j.bmc.2010.02.034
Mus musculus Mus musculus ED50 0.39 mg.kg-1 10.1021/np50073a020
Mus musculus Mus musculus LD50 2.4 mg.kg-1 10.1016/j.bmc.2010.02.034
Mythimna separata Mythimna separata AFI 55.0 % 10.1021/jf300146n
Rattus norvegicus PC-12 Activity nan None 10.1021/np800700e
Trypanosoma brucei brucei Trypanosoma brucei brucei IC50 12900.0 nM 10.1016/j.bmc.2010.02.034
Trypanosoma brucei rhodesiense Rhodesain IC50 45000.0 nM 10.1016/j.bmc.2010.02.034
None ADMET Activity 1.0 uM 10.1016/j.bmc.2010.02.034
None Molecular identity unknown MIC 12200.0 nM 10.1016/j.bmc.2010.02.034
None Unchecked IC50 50000.0 nM 10.1016/j.bmc.2010.02.034
None Unchecked Ratio IC50 7.5 None 10.1016/j.bmc.2010.02.034

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT005209 CC(C)=CCOP(=O)(O)OP(=O)(O)O.COc1ccc2c3c4n(c2c1)[C@H](C=C(C)C)OOC(C)(C)C[C@@H]4N1C(=O)[C@@H]2CCCN2C(=O)[C@]1(O)[C@H]3O>>COc1ccc2c3c4n(c2c1)[C@H](C=C(C)C)OOC(C)(C)C[C@@H]4N1C(=O)[C@@H]2CCCN2C(=O)[C@]1(O)[C@H]3OCC=C(C)C None
AKRT011926 COc1ccc2c3c4n(c2c1)[C@H](C=C(C)C)OOC(C)(C)C[C@@H]4N1C(=O)[C@@H]2CCCN2C(=O)[C@]1(O)[C@H]3O.CC(C)=CCOP(=O)(O)OP(=O)(O)O>>COc1ccc2c3c4n(c2c1)[C@H](C=C(C)C)OOC(C)(C)C[C@@H]4N1C(=O)[C@@H]2CCCN2C(=O)[C@]1(O)[C@H]3OCC=C(C)C enzymemap_39845