NP-MRD: Showing NP-Card for VM-55599 (NP0022806)

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Record Information

Version

2.0

Created at

2021-01-06 07:58:20 UTC

Updated at

2021-07-15 17:40:02 UTC

NP-MRD ID

NP0022806

Secondary Accession Numbers

None

Natural Product Identification

Common Name

VM-55599

Provided By

NPAtlas

Description

VM-55599 belongs to the class of organic compounds known as pyrroloquinolines. Pyrroloquinolines are compounds containing a pyrroloquinoline moiety, which consists of a pyrrole ring fused to a quinoline. VM-55599 is found in Penicillium, Penicillium fellutanum and Penicillium sp.IMI332995. VM-55599 was first documented in 2020 (PMID: 32953008). Based on a literature review very few articles have been published on VM-55599.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105373D          

 53 58  0  0  0  0            999 V2000
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    3.3291    1.8729    0.6182 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2476    0.9201    0.6865 N   0  0  1  0  0  0  0  0  0  0  0  0
    0.9624    1.4665    0.4112 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2667    0.7341   -0.7383 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 53 58  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242105373D          

 53 58  0  0  0  0            999 V2000
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   -6.2036    2.8509   -0.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8463    2.7636   -1.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5979   -2.7862   -1.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4581   -3.3404    0.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0309   -3.2305   -0.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3429   -0.6973    2.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1782   -1.5779    2.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2429   -2.5190    1.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1399   -1.1755   -1.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0441   -2.0801   -0.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7093   -1.4907    0.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7542    1.4931   -2.7605 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 23  2  1  0  0  0  0
 23  5  1  0  0  0  0
 21  7  1  0  0  0  0
  7 26  1  6  0  0  0
 17  9  1  0  0  0  0
 17 12  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  2 30  1  6  0  0  0
  3 31  1  0  0  0  0
  3 32  1  0  0  0  0
  4 33  1  0  0  0  0
  4 34  1  0  0  0  0
  6 35  1  0  0  0  0
  6 36  1  0  0  0  0
  8 37  1  0  0  0  0
  8 38  1  0  0  0  0
 11 39  1  0  0  0  0
 13 40  1  0  0  0  0
 14 41  1  0  0  0  0
 15 42  1  0  0  0  0
 16 43  1  0  0  0  0
 19 44  1  0  0  0  0
 19 45  1  0  0  0  0
 19 46  1  0  0  0  0
 20 47  1  0  0  0  0
 20 48  1  0  0  0  0
 20 49  1  0  0  0  0
 21 50  1  6  0  0  0
 22 51  1  0  0  0  0
 22 52  1  0  0  0  0
 26 53  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0022806

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N1C2=C([H])C([H])=C([H])C([H])=C2C2=C1C(C([H])([H])[H])(C([H])([H])[H])[C@]1([H])C([H])([H])[C@@]34N(C([H])([H])C([H])([H])[C@@]3([H])C([H])([H])[H])C([H])([H])[C@]1(N([H])C4=O)C2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H27N3O/c1-13-8-9-25-12-21-10-15-14-6-4-5-7-16(14)23-18(15)20(2,3)17(21)11-22(13,25)19(26)24-21/h4-7,13,17,23H,8-12H2,1-3H3,(H,24,26)/t13-,17+,21-,22-/m1/s1

> <INCHI_KEY>
FBXHMCWNISYEEV-FXQDWMKTSA-N

> <FORMULA>
C22H27N3O

> <MOLECULAR_WEIGHT>
349.478

> <EXACT_MASS>
349.215412501

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
40.38521264686387

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,13S,15R,16R)-12,12,16-trimethyl-10,19,21-triazahexacyclo[13.5.2.0^{1,13}.0^{3,11}.0^{4,9}.0^{15,19}]docosa-3(11),4,6,8-tetraen-22-one

> <ALOGPS_LOGP>
3.54

> <JCHEM_LOGP>
2.9504423483333335

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.583261929614782

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.667891739011903

> <JCHEM_PKA_STRONGEST_BASIC>
7.854687756178956

> <JCHEM_POLAR_SURFACE_AREA>
48.13

> <JCHEM_REFRACTIVITY>
102.11089999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.68e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,13S,15R,16R)-12,12,16-trimethyl-10,19,21-triazahexacyclo[13.5.2.0^{1,13}.0^{3,11}.0^{4,9}.0^{15,19}]docosa-3(11),4,6,8-tetraen-22-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 53 58  0  0  0  0  0  0  0  0999 V2000
    4.2724   -1.4999    0.8632 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0771   -0.3297   -0.0525 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5531    0.9732    0.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3291    1.8729    0.6182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2476    0.9201    0.6865 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9624    1.4665    0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2667    0.7341   -0.7383 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0832    1.2627   -1.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1669    0.5378   -0.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9862   -0.6595    0.3026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1542   -1.0407    0.8453 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0884   -0.1062    0.5942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4227   -0.0775    0.9575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1921    0.9942    0.5837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6055    2.0095   -0.1442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2685    1.9654   -0.4997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4748    0.8859   -0.1286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6873   -1.3515    0.3155 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9651   -2.7790   -0.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2496   -1.5131    1.7469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3297   -0.7615   -0.5829 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7235   -1.2012   -0.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6560   -0.0374   -0.3546 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4674    0.6177   -1.7025 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3788    0.7708   -2.5250 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1066    1.0365   -1.9057 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1645   -2.4284    0.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2901   -1.5058    1.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5644   -1.5050    1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6140   -0.5096   -1.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542    0.7414    1.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3758    1.4310   -0.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2892    2.4902   -0.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3349    2.4740    1.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3378    1.5454    1.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0787    2.5249    0.0305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3594    1.2617   -2.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1050    2.3521   -0.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3276   -1.9350    1.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8663   -0.8732    1.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2513    1.0363    0.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2036    2.8509   -0.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8463    2.7636   -1.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5979   -2.7862   -1.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4581   -3.3404    0.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0309   -3.2305   -0.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3429   -0.6973    2.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1782   -1.5779    2.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2429   -2.5190    1.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1399   -1.1755   -1.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0441   -2.0801   -0.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7093   -1.4907    0.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7542    1.4931   -2.7605 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10 18  1  0
 18 19  1  6
 18 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  6
 24 25  2  0
 24 26  1  0
 23  2  1  0
 23  5  1  0
 21  7  1  0
  7 26  1  6
 17  9  1  0
 17 12  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  6
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  6 35  1  0
  6 36  1  0
  8 37  1  0
  8 38  1  0
 11 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 16 43  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  6
 22 51  1  0
 22 52  1  0
 26 53  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       4.272  -1.500   0.863  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.077  -0.330  -0.053  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.553   0.973   0.583  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.329   1.873   0.618  0.00  0.00           C+0
HETATM    5  N   UNK     0       2.248   0.920   0.687  0.00  0.00           N+0
HETATM    6  C   UNK     0       0.962   1.466   0.411  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.267   0.734  -0.738  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.083   1.263  -1.016  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.167   0.538  -0.308  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.986  -0.660   0.303  0.00  0.00           C+0
HETATM   11  N   UNK     0      -3.154  -1.041   0.845  0.00  0.00           N+0
HETATM   12  C   UNK     0      -4.088  -0.106   0.594  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.423  -0.078   0.958  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.192   0.994   0.584  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.606   2.010  -0.144  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.269   1.965  -0.500  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.475   0.886  -0.129  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.687  -1.351   0.316  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.965  -2.779  -0.188  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.250  -1.513   1.747  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.330  -0.762  -0.583  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.724  -1.201  -0.226  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.656  -0.037  -0.355  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.467   0.618  -1.702  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.379   0.771  -2.525  0.00  0.00           O+0
HETATM   26  N   UNK     0       1.107   1.036  -1.906  0.00  0.00           N+0
HETATM   27  H   UNK     0       4.165  -2.428   0.273  0.00  0.00           H+0
HETATM   28  H   UNK     0       5.290  -1.506   1.298  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.564  -1.505   1.704  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.614  -0.510  -1.006  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.854   0.741   1.611  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.376   1.431  -0.019  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.289   2.490  -0.301  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.335   2.474   1.550  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.338   1.545   1.302  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.079   2.525   0.031  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.359   1.262  -2.101  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.105   2.352  -0.718  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.328  -1.935   1.389  0.00  0.00           H+0
HETATM   40  H   UNK     0      -5.866  -0.873   1.523  0.00  0.00           H+0
HETATM   41  H   UNK     0      -7.251   1.036   0.862  0.00  0.00           H+0
HETATM   42  H   UNK     0      -6.204   2.851  -0.439  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.846   2.764  -1.061  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.598  -2.786  -1.074  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.458  -3.340   0.644  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.031  -3.231  -0.343  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.343  -0.697   2.145  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.178  -1.578   2.375  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.243  -2.519   1.891  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.140  -1.176  -1.619  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.044  -2.080  -0.821  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.709  -1.491   0.856  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.754   1.493  -2.761  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    1    3   23   30                                             
CONECT    3    2    4   31   32                                             
CONECT    4    3    5   33   34                                             
CONECT    5    4    6   23                                                  
CONECT    6    5    7   35   36                                             
CONECT    7    6    8   21   26                                             
CONECT    8    7    9   37   38                                             
CONECT    9    8   10   17                                                  
CONECT   10    9   11   18                                                  
CONECT   11   10   12   39                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14   40                                                  
CONECT   14   13   15   41                                                  
CONECT   15   14   16   42                                                  
CONECT   16   15   17   43                                                  
CONECT   17   16    9   12                                                  
CONECT   18   10   19   20   21                                             
CONECT   19   18   44   45   46                                             
CONECT   20   18   47   48   49                                             
CONECT   21   18   22    7   50                                             
CONECT   22   21   23   51   52                                             
CONECT   23   22   24    2    5                                             
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    7   53                                                  
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    2                                                            
CONECT   31    3                                                            
CONECT   32    3                                                            
CONECT   33    4                                                            
CONECT   34    4                                                            
CONECT   35    6                                                            
CONECT   36    6                                                            
CONECT   37    8                                                            
CONECT   38    8                                                            
CONECT   39   11                                                            
CONECT   40   13                                                            
CONECT   41   14                                                            
CONECT   42   15                                                            
CONECT   43   16                                                            
CONECT   44   19                                                            
CONECT   45   19                                                            
CONECT   46   19                                                            
CONECT   47   20                                                            
CONECT   48   20                                                            
CONECT   49   20                                                            
CONECT   50   21                                                            
CONECT   51   22                                                            
CONECT   52   22                                                            
CONECT   53   26                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  116    0
END

RDKit          3D

53 58  0  0  0  0  0  0  0  0999 V2000
    4.2724   -1.4999    0.8632 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0771   -0.3297   -0.0525 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5531    0.9732    0.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3291    1.8729    0.6182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2476    0.9201    0.6865 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9624    1.4665    0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2667    0.7341   -0.7383 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0832    1.2627   -1.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1669    0.5378   -0.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9862   -0.6595    0.3026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1542   -1.0407    0.8453 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0884   -0.1062    0.5942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4227   -0.0775    0.9575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1921    0.9942    0.5837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6055    2.0095   -0.1442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2685    1.9654   -0.4997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4748    0.8859   -0.1286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6873   -1.3515    0.3155 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9651   -2.7790   -0.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2496   -1.5131    1.7469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3297   -0.7615   -0.5829 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7235   -1.2012   -0.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6560   -0.0374   -0.3546 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4674    0.6177   -1.7025 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3788    0.7708   -2.5250 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1066    1.0365   -1.9057 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1645   -2.4284    0.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2901   -1.5058    1.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5644   -1.5050    1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6140   -0.5096   -1.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542    0.7414    1.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3758    1.4310   -0.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2892    2.4902   -0.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3349    2.4740    1.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3378    1.5454    1.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0787    2.5249    0.0305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3594    1.2617   -2.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1050    2.3521   -0.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3276   -1.9350    1.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8663   -0.8732    1.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2513    1.0363    0.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2036    2.8509   -0.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8463    2.7636   -1.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5979   -2.7862   -1.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4581   -3.3404    0.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0309   -3.2305   -0.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3429   -0.6973    2.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1782   -1.5779    2.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2429   -2.5190    1.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1399   -1.1755   -1.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0441   -2.0801   -0.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7093   -1.4907    0.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7542    1.4931   -2.7605 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10 18  1  0
 18 19  1  6
 18 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  6
 24 25  2  0
 24 26  1  0
 23  2  1  0
 23  5  1  0
 21  7  1  0
  7 26  1  6
 17  9  1  0
 17 12  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  6
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  6 35  1  0
  6 36  1  0
  8 37  1  0
  8 38  1  0
 11 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 16 43  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  6
 22 51  1  0
 22 52  1  0
 26 53  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₂H₂₇N₃O

Average Mass

349.4780 Da

Monoisotopic Mass

349.21541 Da

IUPAC Name

(1S,13S,15R,16R)-12,12,16-trimethyl-10,19,21-triazahexacyclo[13.5.2.0^{1,13}.0^{3,11}.0^{4,9}.0^{15,19}]docosa-3(11),4,6,8-tetraen-22-one

Traditional Name

(1S,13S,15R,16R)-12,12,16-trimethyl-10,19,21-triazahexacyclo[13.5.2.0^{1,13}.0^{3,11}.0^{4,9}.0^{15,19}]docosa-3(11),4,6,8-tetraen-22-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1CCN2C[C@]34CC5=C(NC6=CC=CC=C56)C(C)(C)[C@@H]3C[C@]12C(=O)N4

InChI Identifier

InChI=1S/C22H27N3O/c1-13-8-9-25-12-21-10-15-14-6-4-5-7-16(14)23-18(15)20(2,3)17(21)11-22(13,25)19(26)24-21/h4-7,13,17,23H,8-12H2,1-3H3,(H,24,26)/t13-,17+,21-,22-/m1/s1

InChI Key

FBXHMCWNISYEEV-FXQDWMKTSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Penicillium	NPAtlas	8226314
Penicillium fellutanum	Fungi	KNApSAcK
Penicillium sp.IMI332995	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloquinolines. Pyrroloquinolines are compounds containing a pyrroloquinoline moiety, which consists of a pyrrole ring fused to a quinoline.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Pyrroloquinolines

Direct Parent

Pyrroloquinolines

Alternative Parents

Substituents

Carbazole
Pyrroloquinoline
Alpha-amino acid amide
Alpha-amino acid or derivatives
Azaspirodecane
3-alkylindole
Indole
Indole or derivatives
Indolizidine
Delta-lactam
Aralkylamine
Piperidinone
N-alkylpiperazine
1,4-diazinane
Benzenoid
Piperazine
Piperidine
N-alkylpyrrolidine
Pyrrolidine
Pyrrole
Heteroaromatic compound
Tertiary amine
Amino acid or derivatives
Secondary carboxylic acid amide
Tertiary aliphatic amine
Lactam
Carboxamide group
Azacycle
Carboxylic acid derivative
Amine
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.54	ALOGPS
logP	2.95	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	12.67	ChemAxon
pKa (Strongest Basic)	7.85	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	48.13 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	102.11 m³·mol⁻¹	ChemAxon
Polarizability	40.39 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA000137

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00026835

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139583125

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Roque JB, Mercado-Marin EV, Richter SC, Pereira de Sant'Ana D, Mukai K, Ye Y, Sarpong R: A unified strategy to reverse-prenylated indole alkaloids: total syntheses of preparaherquamide, premalbrancheamide, and (+)-VM-55599. Chem Sci. 2020 May 28;11(23):5929-5934. doi: 10.1039/d0sc02296a. eCollection 2020 Jun 21. [PubMed:32953008 ]

Showing NP-Card for VM-55599 (NP0022806)

MOL for NP0022806 (VM-55599)

3D MOL for NP0022806 (VM-55599)

3D SDF for NP0022806 (VM-55599)

3D-SDF for NP0022806 (VM-55599)

PDB for NP0022806 (VM-55599)

3D PDB for NP0022806 (VM-55599)

SMILES for NP0022806 (VM-55599)

INCHI for NP0022806 (VM-55599)

Structure for NP0022806 (VM-55599)

3D Structure for NP0022806 (VM-55599)