MiMeDB: Showing metabocard for Brevianamide S (MMDBc0017045)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 07:31:28 UTC

Update Date

2025-10-07 16:06:37 UTC

Metabolite ID

MMDBc0017045

Metabolite Identification

Common Name

Brevianamide S

Description

Brevianamide S is a dimeric diketopiperazine alkaloid known for its potential in antimicrobial applications. Its chemical structure features a unique arrangement of amino acid residues that contribute to its biological activity. The first total synthesis of brevianamide S has been achieved in eight steps, showcasing its complex synthesis pathway (PMID:40151154 ). Isolated from Aspergillus versicolor found in sediment from the Bohai Sea, China, brevianamide S was discovered alongside three new monomeric cometabolites (PMID:22963079 ). This compound exhibits selective antibacterial activity against Bacille Calmette-Guérin (BCG), indicating a novel mechanism of action that may be leveraged for the development of next-generation antitubercular agents (PMID:22963079 ). The proposed mechanism of action remains to be fully elucidated, highlighting the compound's potential as a promising lead in drug development (PMID:40151154 ). Overall, brevianamide S represents a significant advancement in the search for effective treatments against tuberculosis and other bacterial infections.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152109312D          

 54 61  0  0  0  0            999 V2000
   -3.9990   -4.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9060    3.3265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2358   -3.4336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8498   -3.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1545    1.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5406    2.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2143   -4.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5191    2.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9068    0.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2115   -1.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7137    0.2702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0185   -1.5647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6518   -0.6859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9565   -0.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2658   -0.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5705   -0.9516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0098   -1.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -2.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4031   -2.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2038   -1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5086    0.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1176   -2.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0108   -1.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3155   -0.1670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6887   -2.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7403   -1.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8713   -2.4551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1760    1.1606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0258   -0.8820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0258   -2.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0428   -3.2620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3475    1.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4233   -1.8420    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7280    0.5475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6887   -1.2945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7403   -2.1195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0258   -0.0570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0258   -3.3570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4031   -3.3570    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  2  0  0  0  0
  8  2  2  0  0  0  0
 11  9  2  0  0  0  0
 12 10  2  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16 12  1  0  0  0  0
 19 17  1  0  0  0  0
 20 18  1  0  0  0  0
 23 13  2  0  0  0  0
 24 14  2  0  0  0  0
 25 17  1  0  0  0  0
 26 18  1  0  0  0  0
 26 25  1  0  0  0  0
 27 21  1  0  0  0  0
 27 23  1  0  0  0  0
 28 22  1  0  0  0  0
 28 24  1  0  0  0  0
 29 15  2  0  0  0  0
 29 23  1  0  0  0  0
 30 16  2  0  0  0  0
 30 24  1  0  0  0  0
 31 21  2  0  0  0  0
 32 22  2  0  0  0  0
 33 25  2  0  0  0  0
 34 26  2  0  0  0  0
 35 27  2  0  0  0  0
 36 28  2  0  0  0  0
 37 33  1  0  0  0  0
 38 34  1  0  0  0  0
 39 31  1  0  0  0  0
 40 32  1  0  0  0  0
 41  3  1  0  0  0  0
 41  4  1  0  0  0  0
 41  7  1  0  0  0  0
 41 35  1  0  0  0  0
 42  5  1  0  0  0  0
 42  6  1  0  0  0  0
 42  8  1  0  0  0  0
 42 36  1  0  0  0  0
 43 29  1  0  0  0  0
 43 35  1  0  0  0  0
 44 30  1  0  0  0  0
 44 36  1  0  0  0  0
 45 31  1  0  0  0  0
 45 37  1  0  0  0  0
 46 32  1  0  0  0  0
 46 38  1  0  0  0  0
 47 19  1  0  0  0  0
 47 33  1  0  0  0  0
 47 39  1  0  0  0  0
 48 20  1  0  0  0  0
 48 34  1  0  0  0  0
 48 40  1  0  0  0  0
 49 37  2  0  0  0  0
 50 38  2  0  0  0  0
 51 39  2  0  0  0  0
 52 40  2  0  0  0  0
 53 21  1  0  0  0  0
 54 22  1  0  0  0  0
M  END


  Mrv1652305152109312D          

 54 61  0  0  0  0            999 V2000
   -3.9990   -4.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9060    3.3265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2358   -3.4336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8498   -3.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1545    1.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5406    2.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2143   -4.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5191    2.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9068    0.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2115   -1.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7137    0.2702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0185   -1.5647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6518   -0.6859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9565   -0.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2658   -0.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5705   -0.9516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0098   -1.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -2.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4031   -2.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2038   -1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5086    0.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1176   -2.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0108   -1.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3155   -0.1670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6887   -2.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7403   -1.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8713   -2.4551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1760    1.1606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0258   -0.8820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0258   -2.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0428   -3.2620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3475    1.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4233   -1.8420    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7280    0.5475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6887   -1.2945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7403   -2.1195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0258   -0.0570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0258   -3.3570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4031   -3.3570    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  2  0  0  0  0
  8  2  2  0  0  0  0
 11  9  2  0  0  0  0
 12 10  2  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16 12  1  0  0  0  0
 19 17  1  0  0  0  0
 20 18  1  0  0  0  0
 23 13  2  0  0  0  0
 24 14  2  0  0  0  0
 25 17  1  0  0  0  0
 26 18  1  0  0  0  0
 26 25  1  0  0  0  0
 27 21  1  0  0  0  0
 27 23  1  0  0  0  0
 28 22  1  0  0  0  0
 28 24  1  0  0  0  0
 29 15  2  0  0  0  0
 29 23  1  0  0  0  0
 30 16  2  0  0  0  0
 30 24  1  0  0  0  0
 31 21  2  0  0  0  0
 32 22  2  0  0  0  0
 33 25  2  0  0  0  0
 34 26  2  0  0  0  0
 35 27  2  0  0  0  0
 36 28  2  0  0  0  0
 37 33  1  0  0  0  0
 38 34  1  0  0  0  0
 39 31  1  0  0  0  0
 40 32  1  0  0  0  0
 41  3  1  0  0  0  0
 41  4  1  0  0  0  0
 41  7  1  0  0  0  0
 41 35  1  0  0  0  0
 42  5  1  0  0  0  0
 42  6  1  0  0  0  0
 42  8  1  0  0  0  0
 42 36  1  0  0  0  0
 43 29  1  0  0  0  0
 43 35  1  0  0  0  0
 44 30  1  0  0  0  0
 44 36  1  0  0  0  0
 45 31  1  0  0  0  0
 45 37  1  0  0  0  0
 46 32  1  0  0  0  0
 46 38  1  0  0  0  0
 47 19  1  0  0  0  0
 47 33  1  0  0  0  0
 47 39  1  0  0  0  0
 48 20  1  0  0  0  0
 48 34  1  0  0  0  0
 48 40  1  0  0  0  0
 49 37  2  0  0  0  0
 50 38  2  0  0  0  0
 51 39  2  0  0  0  0
 52 40  2  0  0  0  0
 53 21  1  0  0  0  0
 54 22  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0017045

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(C1=C(NC2=CC=CC=C12)C(C)(C)C=C)=C1\NC(=O)C2=C(CCN2C1=O)C1=C2N(CC1)C(=O)\C(NC2=O)=C(/[H])C1=C(NC2=CC=CC=C12)C(C)(C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C42H40N6O4/c1-7-41(3,4)35-27(23-13-9-11-15-29(23)43-35)21-31-39(51)47-19-17-25(33(47)37(49)45-31)26-18-20-48-34(26)38(50)46-32(40(48)52)22-28-24-14-10-12-16-30(24)44-36(28)42(5,6)8-2/h7-16,21-22,43-44H,1-2,17-20H2,3-6H3,(H,45,49)(H,46,50)/b31-21-,32-22-

> <INCHI_KEY>
PGXKQZMVWMPSQA-RYJWMXFHSA-N

> <FORMULA>
C42H40N6O4

> <MOLECULAR_WEIGHT>
692.82

> <EXACT_MASS>
692.311103792

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
92

> <JCHEM_AVERAGE_POLARIZABILITY>
77.48516786548129

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3Z)-3-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene}-8-[(3Z)-3-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene}-1,4-dioxo-1H,2H,3H,4H,6H,7H-pyrrolo[1,2-a]pyrazin-8-yl]-1H,2H,3H,4H,6H,7H-pyrrolo[1,2-a]pyrazine-1,4-dione

> <ALOGPS_LOGP>
5.91

> <JCHEM_LOGP>
4.7870311359999995

> <ALOGPS_LOGS>
-5.70

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.529946070678716

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.926624282555775

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6875007892712444

> <JCHEM_POLAR_SURFACE_AREA>
130.39999999999998

> <JCHEM_REFRACTIVITY>
206.18959999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.39e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3Z)-3-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene}-8-[(3Z)-3-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene}-1,4-dioxo-2H,6H,7H-pyrrolo[1,2-a]pyrazin-8-yl]-2H,6H,7H-pyrrolo[1,2-a]pyrazine-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0      -7.465  -8.071   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.024   6.210   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.174  -6.409   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.186  -5.769   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.355   3.353   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.342   3.993   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.000  -7.595   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.169   5.179   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.559   0.184   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.728  -2.601   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.066   0.504   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.234  -2.921   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.083  -1.280   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.252  -1.136   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.096  -0.640   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.265  -1.776   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.752  -3.186   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.846  -4.432   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.619  -4.726   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.788   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.114  -2.425   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.283   0.008   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.846  -1.941   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.953  -3.956   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.122   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.620  -2.105   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.789  -0.312   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.286  -3.956   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.382  -2.416   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -5.360  -4.583   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.529   2.166   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.048  -1.646   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.048  -4.726   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -5.680  -6.089   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      11.849   3.673   0.000  0.00  0.00           C+0
HETATM   43  N   UNK     0      -6.390  -3.438   0.000  0.00  0.00           N+0
HETATM   44  N   UNK     0      12.559   1.022   0.000  0.00  0.00           N+0
HETATM   45  N   UNK     0      -1.286  -2.416   0.000  0.00  0.00           N+0
HETATM   46  N   UNK     0       7.454   0.000   0.000  0.00  0.00           N+0
HETATM   47  N   UNK     0       1.382  -3.956   0.000  0.00  0.00           N+0
HETATM   48  N   UNK     0       4.787   1.540   0.000  0.00  0.00           N+0
HETATM   49  O   UNK     0       0.048  -0.106   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0       0.048  -6.266   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       6.121   3.850   0.000  0.00  0.00           O+0
HETATM   53  H   UNK     0      -2.619  -6.266   0.000  0.00  0.00           H+0
HETATM   54  H   UNK     0       8.788   3.850   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3   41                                                            
CONECT    4   41                                                            
CONECT    5   42                                                            
CONECT    6   42                                                            
CONECT    7    1   41                                                       
CONECT    8    2   42                                                       
CONECT    9   11   13                                                       
CONECT   10   12   14                                                       
CONECT   11    9   15                                                       
CONECT   12   10   16                                                       
CONECT   13    9   23                                                       
CONECT   14   10   24                                                       
CONECT   15   11   29                                                       
CONECT   16   12   30                                                       
CONECT   17   19   25                                                       
CONECT   18   20   26                                                       
CONECT   19   17   47                                                       
CONECT   20   18   48                                                       
CONECT   21   27   31   53                                                  
CONECT   22   28   32   54                                                  
CONECT   23   13   27   29                                                  
CONECT   24   14   28   30                                                  
CONECT   25   17   26   33                                                  
CONECT   26   18   25   34                                                  
CONECT   27   21   23   35                                                  
CONECT   28   22   24   36                                                  
CONECT   29   15   23   43                                                  
CONECT   30   16   24   44                                                  
CONECT   31   21   39   45                                                  
CONECT   32   22   40   46                                                  
CONECT   33   25   37   47                                                  
CONECT   34   26   38   48                                                  
CONECT   35   27   41   43                                                  
CONECT   36   28   42   44                                                  
CONECT   37   33   45   49                                                  
CONECT   38   34   46   50                                                  
CONECT   39   31   47   51                                                  
CONECT   40   32   48   52                                                  
CONECT   41    3    4    7   35                                             
CONECT   42    5    6    8   36                                             
CONECT   43   29   35                                                       
CONECT   44   30   36                                                       
CONECT   45   31   37                                                       
CONECT   46   32   38                                                       
CONECT   47   19   33   39                                                  
CONECT   48   20   34   40                                                  
CONECT   49   37                                                            
CONECT   50   38                                                            
CONECT   51   39                                                            
CONECT   52   40                                                            
CONECT   53   21                                                            
CONECT   54   22                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  122    0
END

Synonyms

Not Available

Molecular Formula

C₄₂H₄₀N₆O₄

Average Mass

692.82

Monoisotopic Mass

692.311103792

IUPAC Name

(3Z)-3-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene}-8-[(3Z)-3-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene}-1,4-dioxo-1H,2H,3H,4H,6H,7H-pyrrolo[1,2-a]pyrazin-8-yl]-1H,2H,3H,4H,6H,7H-pyrrolo[1,2-a]pyrazine-1,4-dione

Traditional Name

(3Z)-3-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene}-8-[(3Z)-3-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene}-1,4-dioxo-2H,6H,7H-pyrrolo[1,2-a]pyrazin-8-yl]-2H,6H,7H-pyrrolo[1,2-a]pyrazine-1,4-dione

CAS Registry Number

Not Available

SMILES

[H]\C(C1=C(NC2=CC=CC=C12)C(C)(C)C=C)=C1\NC(=O)C2=C(CCN2C1=O)C1=C2N(CC1)C(=O)\C(NC2=O)=C(/[H])C1=C(NC2=CC=CC=C12)C(C)(C)C=C

InChI Identifier

InChI=1S/C42H40N6O4/c1-7-41(3,4)35-27(23-13-9-11-15-29(23)43-35)21-31-39(51)47-19-17-25(33(47)37(49)45-31)26-18-20-48-34(26)38(50)46-32(40(48)52)22-28-24-14-10-12-16-30(24)44-36(28)42(5,6)8-2/h7-16,21-22,43-44H,1-2,17-20H2,3-6H3,(H,45,49)(H,46,50)/b31-21-,32-22-

InChI Key

PGXKQZMVWMPSQA-RYJWMXFHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolopyrazines. Pyrrolopyrazines are compounds containing a pyrrolopyrazine moiety, which consists of a pyrrole ring fused to a pyrazine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Pyrazine is a 6-membered ring consisting of six carbon atoms and two nitrogen centers at ring positions 1 and 4.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolopyrazines

Sub Class

Not Available

Direct Parent

Pyrrolopyrazines

Alternative Parents

Substituents

Indole
Indole or derivatives
Pyrrolopyrazine
Pyrazine
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Lactam
Azacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0014 g/L	ALOGPS
logP	5.91	ALOGPS
logP	4.79	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	6.93	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	130.4 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	206.19 m³·mol⁻¹	ChemAxon
Polarizability	77.49 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28533864

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71480278

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Brevianamide S (MMDBc0017045)

MOL for #<Metabolite:0x00007f8dcfb49e48>

3D MOL for #<Metabolite:0x00007f8dcfb49e48>

3D SDF for #<Metabolite:0x00007f8dcfb49e48>

3D-SDF for #<Metabolite:0x00007f8dcfb49e48>

PDB for #<Metabolite:0x00007f8dcfb49e48>

3D PDB for #<Metabolite:0x00007f8dcfb49e48>

SMILES for #<Metabolite:0x00007f8dcfb49e48>

INCHI for #<Metabolite:0x00007f8dcfb49e48>

Structure for #<Metabolite:0x00007f8dcfb49e48>

3D Structure for #<Metabolite:0x00007f8dcfb49e48>