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Brevianamide F

AlkaPlorer ID: AK012490

Synonym: None

IUPAC Name: (3S,8aS)-3-(1H-indol-3-ylmethyl)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

Structure

SMILES: O=C1[C@H](CC2=CNC3=CC=CC=C23)N=C(O)[C@@H]2CCCN12

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InChI: InChI=1S/C16H17N3O2/c20-15-14-6-3-7-19(14)16(21)13(18-15)8-10-9-17-12-5-2-1-4-11(10)12/h1-2,4-5,9,13-14,17H,3,6-8H2,(H,18,20)/t13-,14-/m0/s1

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InChIKey: RYFZBPVMVYTEKZ-KBPBESRZSA-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: 283.331

TPSA？: 68.69

MolLogP？: 2.0401

Number of H-Donors: 2

Number of H-Acceptors: 2

RingCount: 4

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Artemia salina Artemia salina LC50 83.7 ug.mL-1 10.1021/jf300146n
Aspergillus fumigatus Brevianamide F prenyltransferase Activity nan None 10.1021/np800501m
Aspergillus fumigatus Brevianamide F prenyltransferase Kcat 5.57 /s 10.1021/np800501m
Aspergillus fumigatus Brevianamide F prenyltransferase Km 55000.0 nM 10.1021/np800501m
Aspergillus fumigatus Brevianamide F prenyltransferase Ratio 675.0 None 10.1021/np800501m
Bacillus subtilis Bacillus subtilis MIC 11.9 ug.mL-1 10.1016/j.bmcl.2015.06.010
Candida albicans Candida albicans IZ 25.0 mm 10.1016/j.ejmech.2020.112945
Escherichia coli Escherichia coli MIC 20.0 ug.mL-1 10.1016/j.bmcl.2015.06.010
Homo sapiens A2780 IC50 100000.0 nM 10.1016/j.bmcl.2012.04.119
Homo sapiens ATP-binding cassette sub-family G member 2 Inhibition nan % 10.1016/j.bmcl.2016.11.013
Homo sapiens HeLa IC50 200000.0 nM 10.1039/C3MD20353K
Homo sapiens K562 IC50 100000.0 nM 10.1016/j.bmcl.2012.04.119
Mycobacterium tuberculosis Mycobacterium tuberculosis MIC 44100.0 nM 10.1016/j.ejmech.2020.112945
Mycobacterium tuberculosis Mycobacterium tuberculosis MIC 44170.0 nM 10.1016/j.ejmech.2019.01.026
Staphylococcus aureus Staphylococcus aureus IZ 19.0 mm 10.1016/j.ejmech.2020.112945
Staphylococcus aureus Staphylococcus aureus MIC 12.6 ug.mL-1 10.1016/j.bmcl.2015.06.010

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT000403 *C(=O)[C@@H](N)Cc1c[nH]c2ccccc12.*C(=O)[C@@H]1CCCN1>>O=C1N[C@@H](Cc2c[nH]c3ccccc23)C(=O)N2CCC[C@@H]12 RXN-15642
AKRT005281 CC(C)=CCOP(=O)(O)OP(=O)(O)O.O=C1N[C@@H](Cc2c[nH]c3ccccc23)C(=O)N2CCC[C@@H]12>>C=CC(C)(C)c1[nH]c2ccccc2c1C[C@@H]1NC(=O)[C@@H]2CCCN2C1=O RXN-14419
AKRT005282 CC(C)=CCOP(=O)(O)OP(=O)(O)O.O=C1N[C@@H](Cc2c[nH]c3ccccc23)C(=O)N2CCC[C@@H]12>>CC(C)=CCc1[nH]c2ccccc2c1C[C@@H]1NC(=O)[C@@H]2CCCN2C1=O RXN-14418
AKRT005283 CC(C)=CCOP(=O)(O)OP(=O)(O)O.O=C1N[C@@H](Cc2c[nH]c3ccccc23)C(=O)N2CCC[C@@H]12>>CC(C)=CCc1cccc2[nH]cc(C[C@@H]3NC(=O)[C@@H]4CCCN4C3=O)c12 enzymemap_40452
AKRT005284 CC(C)=CCOP(=O)(O)OP(=O)(O)O.O=C1N[C@@H](Cc2c[nH]c3ccccc23)C(=O)N2CCC[C@@H]12>>CC(C)=CCc1cccc2c(C[C@@H]3NC(=O)[C@@H]4CCCN4C3=O)c[nH]c12 enzymemap_39880
AKRT019772 N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O.O=C(O)[C@@H]1CCCN1>>O=C1N[C@@H](Cc2c[nH]c3ccccc23)C(=O)N2CCC[C@@H]12 R10661