MiMeDB: Showing metabocard for Verruculogen (MMDBc0020349)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 10:21:10 UTC

Update Date

2022-08-31 06:46:38 UTC

Metabolite ID

MMDBc0020349

Metabolite Identification

Common Name

Verruculogen

Description

verruculogen, also known as TR 1, belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. Verruculogen is a mycotoxin produced by certain strains of aspergillus that belongs to a class of naturally occurring 2,5-diketopiperazines. verruculogen is an extremely weak basic (essentially neutral) compound (based on its pKa). It produces tremors in mice due to its neurotoxic properties. It is a potent blocker of calcium-activated potassium channels. Both verruculogen and its isoprenyl derivative fumitremorgin A belong to the only family of alkaloids with an eight-membered endoperoxide ring, and both have been synthesised involving ligand-controlled C–H borylation.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152112212D          

 41 46  0  0  1  0            999 V2000
   -1.0753   -3.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2092   -4.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6445   -3.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9858   -4.3130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8576   -1.6114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9525   -0.7030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5718   -1.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2720   -0.1113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5522   -0.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3740   -0.1148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1090   -2.9311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2092   -1.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0825   -2.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2524   -3.6728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6527   -0.8433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9957   -0.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7580   -1.2990    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6150   -1.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7142   -1.9840    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9320   -2.8733    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8095   -0.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9317   -1.7225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4549   -0.3928    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1126   -1.8128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8681   -0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8210   -3.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2226   -0.6949    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6358   -0.4831    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1935   -2.0908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3449   -1.5108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3327    0.4231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2348   -2.6287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7459    0.6348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1004    0.1210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4769   -0.8795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3004   -3.6115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0828   -3.8730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9649   -2.0977    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1731   -2.6068    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7550   -2.8155    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6872   -0.0907    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  9  8  2  0  0  0  0
 10  6  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14 11  2  0  0  0  0
 15  8  1  0  0  0  0
 15 12  2  0  0  0  0
 16  9  1  0  0  0  0
 17  7  1  0  0  0  0
 18 12  1  0  0  0  0
 18 16  2  0  0  0  0
 19 13  1  0  0  0  0
 20 11  1  1  0  0  0
 21 16  1  0  0  0  0
 22 19  1  0  0  0  0
 22 21  2  0  0  0  0
 23 21  1  0  0  0  0
 24 17  1  0  0  0  0
 26  3  1  0  0  0  0
 26  4  1  0  0  0  0
 26 13  1  0  0  0  0
 27 23  1  0  0  0  0
 27 25  1  0  0  0  0
 28 10  1  0  0  0  0
 28 17  1  0  0  0  0
 28 25  1  0  0  0  0
 29 18  1  0  0  0  0
 29 20  1  0  0  0  0
 29 22  1  0  0  0  0
 30 19  1  0  0  0  0
 30 24  1  0  0  0  0
 30 27  1  0  0  0  0
 23 31  1  6  0  0  0
 32 24  2  0  0  0  0
 33 25  2  0  0  0  0
 27 34  1  6  0  0  0
 35  5  1  0  0  0  0
 35 15  1  0  0  0  0
 36 20  1  0  0  0  0
 37 26  1  0  0  0  0
 37 36  1  0  0  0  0
 17 38  1  6  0  0  0
 19 39  1  6  0  0  0
 20 40  1  1  0  0  0
 23 41  1  1  0  0  0
M  END


  Mrv1652305152112212D          

 41 46  0  0  1  0            999 V2000
   -1.0753   -3.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2092   -4.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6445   -3.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9858   -4.3130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8576   -1.6114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9525   -0.7030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5718   -1.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2720   -0.1113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5522   -0.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3740   -0.1148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1090   -2.9311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2092   -1.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0825   -2.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2524   -3.6728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6527   -0.8433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9957   -0.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7580   -1.2990    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6150   -1.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7142   -1.9840    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9320   -2.8733    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8095   -0.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9317   -1.7225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4549   -0.3928    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1126   -1.8128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8681   -0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8210   -3.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2226   -0.6949    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6358   -0.4831    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1935   -2.0908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3449   -1.5108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3327    0.4231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2348   -2.6287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7459    0.6348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1004    0.1210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4769   -0.8795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3004   -3.6115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0828   -3.8730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9649   -2.0977    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1731   -2.6068    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7550   -2.8155    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6872   -0.0907    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  9  8  2  0  0  0  0
 10  6  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14 11  2  0  0  0  0
 15  8  1  0  0  0  0
 15 12  2  0  0  0  0
 16  9  1  0  0  0  0
 17  7  1  0  0  0  0
 18 12  1  0  0  0  0
 18 16  2  0  0  0  0
 19 13  1  0  0  0  0
 20 11  1  1  0  0  0
 21 16  1  0  0  0  0
 22 19  1  0  0  0  0
 22 21  2  0  0  0  0
 23 21  1  0  0  0  0
 24 17  1  0  0  0  0
 26  3  1  0  0  0  0
 26  4  1  0  0  0  0
 26 13  1  0  0  0  0
 27 23  1  0  0  0  0
 27 25  1  0  0  0  0
 28 10  1  0  0  0  0
 28 17  1  0  0  0  0
 28 25  1  0  0  0  0
 29 18  1  0  0  0  0
 29 20  1  0  0  0  0
 29 22  1  0  0  0  0
 30 19  1  0  0  0  0
 30 24  1  0  0  0  0
 30 27  1  0  0  0  0
 23 31  1  6  0  0  0
 32 24  2  0  0  0  0
 33 25  2  0  0  0  0
 27 34  1  6  0  0  0
 35  5  1  0  0  0  0
 35 15  1  0  0  0  0
 36 20  1  0  0  0  0
 37 26  1  0  0  0  0
 37 36  1  0  0  0  0
 17 38  1  6  0  0  0
 19 39  1  6  0  0  0
 20 40  1  1  0  0  0
 23 41  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0020349

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]12CCCN1C(=O)[C@@]1(O)N(C2=O)[C@@]2([H])CC(C)(C)OO[C@]([H])(C=C(C)C)N3C4=C(C=CC(OC)=C4)C(=C23)[C@]1([H])O

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
LRXYHMMJJCTUMY-GWXUGYLUSA-N

> <FORMULA>
C27H33N3O7

> <MOLECULAR_WEIGHT>
511.575

> <EXACT_MASS>
511.231850415

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
53.426822070933625

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9R,14S,17S,23R,24S)-23,24-dihydroxy-5-methoxy-12,12-dimethyl-9-(2-methylprop-1-en-1-yl)-10,11-dioxa-8,15,21-triazahexacyclo[12.10.1.0^{2,7}.0^{8,25}.0^{15,23}.0^{17,21}]pentacosa-1(25),2(7),3,5-tetraene-16,22-dione

> <ALOGPS_LOGP>
1.72

> <JCHEM_LOGP>
2.4288060700000003

> <ALOGPS_LOGS>
-2.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.527172248601968

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.134767183070624

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7962454905474763

> <JCHEM_POLAR_SURFACE_AREA>
113.70000000000002

> <JCHEM_REFRACTIVITY>
133.0322

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.18e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9R,14S,17S,23R,24S)-23,24-dihydroxy-5-methoxy-12,12-dimethyl-9-(2-methylprop-1-en-1-yl)-10,11-dioxa-8,15,21-triazahexacyclo[12.10.1.0^{2,7}.0^{8,25}.0^{15,23}.0^{17,21}]pentacosa-1(25),2(7),3,5-tetraene-16,22-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      -2.007  -6.964   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.391  -8.132   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.803  -6.635   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.573  -8.051   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.467  -3.008   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.111  -1.312   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.401  -2.679   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.508  -0.208   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.031  -0.140   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.031  -0.214   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.204  -5.471   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.390  -2.873   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.754  -5.081   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.471  -6.856   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.218  -1.574   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.859  -1.439   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.882  -2.425   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.148  -2.805   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.066  -3.703   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.740  -5.363   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.378  -1.692   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.606  -3.215   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.583  -0.733   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.677  -3.384   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.220  -0.338   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.266  -6.542   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.016  -1.297   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       8.654  -0.902   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0       2.228  -3.903   0.000  0.00  0.00           N+0
HETATM   30  N   UNK     0       6.244  -2.820   0.000  0.00  0.00           N+0
HETATM   31  O   UNK     0       4.354   0.790   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       7.905  -4.907   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       6.992   1.185   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       5.787   0.226   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -2.757  -1.642   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       2.427  -6.741   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       3.888  -7.230   0.000  0.00  0.00           O+0
HETATM   38  H   UNK     0       9.268  -3.916   0.000  0.00  0.00           H+0
HETATM   39  H   UNK     0       4.057  -4.866   0.000  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.276  -5.256   0.000  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.149  -0.169   0.000  0.00  0.00           H+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   26                                                            
CONECT    4   26                                                            
CONECT    5   35                                                            
CONECT    6    7   10                                                       
CONECT    7    6   17                                                       
CONECT    8    9   15                                                       
CONECT    9    8   16                                                       
CONECT   10    6   28                                                       
CONECT   11   14   20                                                       
CONECT   12   15   18                                                       
CONECT   13   19   26                                                       
CONECT   14    1    2   11                                                  
CONECT   15    8   12   35                                                  
CONECT   16    9   18   21                                                  
CONECT   17    7   24   28   38                                             
CONECT   18   12   16   29                                                  
CONECT   19   13   22   30   39                                             
CONECT   20   11   29   36   40                                             
CONECT   21   16   22   23                                                  
CONECT   22   19   21   29                                                  
CONECT   23   21   27   31   41                                             
CONECT   24   17   30   32                                                  
CONECT   25   27   28   33                                                  
CONECT   26    3    4   13   37                                             
CONECT   27   23   25   30   34                                             
CONECT   28   10   17   25                                                  
CONECT   29   18   20   22                                                  
CONECT   30   19   24   27                                                  
CONECT   31   23                                                            
CONECT   32   24                                                            
CONECT   33   25                                                            
CONECT   34   27                                                            
CONECT   35    5   15                                                       
CONECT   36   20   37                                                       
CONECT   37   26   36                                                       
CONECT   38   17                                                            
CONECT   39   19                                                            
CONECT   40   20                                                            
CONECT   41   23                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   92    0
END

Synonyms

Value	Source
TR 1	ChEBI
TR 1 Toxin	ChEBI

Molecular Formula

C₂₇H₃₃N₃O₇

Average Mass

511.575

Monoisotopic Mass

511.231850415

IUPAC Name

(9R,14S,17S,23R,24S)-23,24-dihydroxy-5-methoxy-12,12-dimethyl-9-(2-methylprop-1-en-1-yl)-10,11-dioxa-8,15,21-triazahexacyclo[12.10.1.0^{2,7}.0^{8,25}.0^{15,23}.0^{17,21}]pentacosa-1(25),2(7),3,5-tetraene-16,22-dione

Traditional Name

CAS Registry Number

Not Available

SMILES

[H][C@@]12CCCN1C(=O)[C@@]1(O)N(C2=O)[C@@]2([H])CC(C)(C)OO[C@]([H])(C=C(C)C)N3C4=C(C=CC(OC)=C4)C(=C23)[C@]1([H])O

InChI Identifier

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

InChI Key

LRXYHMMJJCTUMY-GWXUGYLUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyridoindoles

Direct Parent

Beta carbolines

Alternative Parents

Substituents

Beta-carboline
Alpha-amino acid or derivatives
3-alkylindole
Indole
Anisole
Dioxopiperazine
2,5-dioxopiperazine
Alkyl aryl ether
N-alkylpiperazine
1,4-diazinane
Piperazine
Benzenoid
Tertiary carboxylic acid amide
Pyrrolidine
Pyrrole
Heteroaromatic compound
Secondary alcohol
Dialkyl peroxide
Lactam
Carboxamide group
Oxacycle
Alkanolamine
Azacycle
Ether
Carboxylic acid derivative
Organooxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:72765 )
organic heterohexacyclic compound (CHEBI:72765 )
indole alkaloid (CHEBI:72765 )
diol (CHEBI:72765 )
organic peroxide (CHEBI:72765 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.18 g/L	ALOGPS
logP	1.72	ALOGPS
logP	2.43	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	10.13	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	113.7 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	133.03 m³·mol⁻¹	ChemAxon
Polarizability	53.43 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	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

Metabolic Reactions

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	11	Human sputum; Human ; Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	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

10405461

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Verruculogen

METLIN ID

Not Available

PubChem Compound

13887805

PDB ID

Not Available

ChEBI ID

72765

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for Verruculogen (MMDBc0020349)

MOL for #<Metabolite:0x00007f46d82ed2d8>

3D MOL for #<Metabolite:0x00007f46d82ed2d8>

3D SDF for #<Metabolite:0x00007f46d82ed2d8>

3D-SDF for #<Metabolite:0x00007f46d82ed2d8>

PDB for #<Metabolite:0x00007f46d82ed2d8>

3D PDB for #<Metabolite:0x00007f46d82ed2d8>

SMILES for #<Metabolite:0x00007f46d82ed2d8>

INCHI for #<Metabolite:0x00007f46d82ed2d8>

Structure for #<Metabolite:0x00007f46d82ed2d8>

3D Structure for #<Metabolite:0x00007f46d82ed2d8>