NP-MRD: Showing NP-Card for Metatacarboline F (NP0011441)

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Record Information

Version

2.0

Created at

2021-01-05 21:07:54 UTC

Updated at

2021-07-15 17:08:56 UTC

NP-MRD ID

NP0011441

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Metatacarboline F

Provided By

NPAtlas

Description

Metatacarboline F belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole. Metatacarboline F is found in Mycena metata. Based on a literature review very few articles have been published on Metatacarboline F.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242116563D          

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M  END

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  Mrv1652306242116563D          

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    0.7492    0.9465   -0.5092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1773    0.7425   -0.8425 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8557   -0.2501    0.0596 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2859   -0.4359   -0.2940 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7281    0.2561   -1.2300 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1017   -1.3656    0.4141 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5957   -2.1762    1.5406 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4402   -3.4127    1.5373 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6874   -3.1018    0.8037 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4761   -1.7087    0.2598 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9934   -1.6663   -1.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2298   -1.5476   -2.0907 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3880   -1.7694   -1.2861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2655    0.4284   -1.2189 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.6321    1.7773   -2.8582 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.0629   -3.1093   -2.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1206   -2.2112   -1.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7784   -0.3730    0.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0374    0.1522   -0.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2307   -1.4305   -0.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4015   -1.0408   -3.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3926    0.7253   -0.7825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9794    1.5352    0.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2056    2.4199    1.5344 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7484    3.9776    3.7383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1010    4.9388    5.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4426    4.4582    4.5117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9577    3.0190    2.5065 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1925    0.3170   -1.8711 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6569    1.7566   -0.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8455    0.1569    1.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3059   -1.1955   -0.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5528   -2.4549    1.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7813   -1.6157    2.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6301   -3.7661    2.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9000   -4.2865    1.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7642   -3.7939   -0.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6168   -3.1895    1.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1138   -1.0432    0.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9591   -1.2078   -0.6665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4658   -0.2461   -4.8565 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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
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 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 19 32  2  0  0  0  0
  4 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 32  8  1  0  0  0  0
 18 10  1  0  0  0  0
 28 24  1  0  0  0  0
 18 13  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  1 38  1  0  0  0  0
  2 39  1  1  0  0  0
  3 40  1  0  0  0  0
  3 41  1  0  0  0  0
  3 42  1  0  0  0  0
  4 43  1  6  0  0  0
  5 44  1  0  0  0  0
  9 45  1  0  0  0  0
 12 46  1  0  0  0  0
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 27 60  1  0  0  0  0
 28 61  1  1  0  0  0
 31 62  1  0  0  0  0
 35 63  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0011441

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@@]([H])(N([H])C(=O)C1=C([H])C2=C(N([H])C3=C([H])C([H])=C([H])C([H])=C23)C(=N1)C([H])([H])C([H])([H])C(=O)N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(=O)O[H])C([H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H28N4O6/c1-13(2)21(25(34)35)28-23(31)18-12-15-14-6-3-4-7-16(14)27-22(15)17(26-18)9-10-20(30)29-11-5-8-19(29)24(32)33/h3-4,6-7,12-13,19,21,27H,5,8-11H2,1-2H3,(H,28,31)(H,32,33)(H,34,35)/t19-,21-/m0/s1

> <INCHI_KEY>
VDVKKTJHKSSCRY-FPOVZHCZSA-N

> <FORMULA>
C25H28N4O6

> <MOLECULAR_WEIGHT>
480.521

> <EXACT_MASS>
480.200884638

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
51.42453366294984

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-1-[3-(3-{[(1S)-1-carboxy-2-methylpropyl]carbamoyl}-9H-pyrido[3,4-b]indol-1-yl)propanoyl]pyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
1.68

> <JCHEM_LOGP>
1.960002216333333

> <ALOGPS_LOGS>
-3.88

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.111282289546681

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.502088882117336

> <JCHEM_PKA_STRONGEST_BASIC>
0.5239202892367443

> <JCHEM_POLAR_SURFACE_AREA>
152.69

> <JCHEM_REFRACTIVITY>
124.96379999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.28e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-[3-(3-{[(1S)-1-carboxy-2-methylpropyl]carbamoyl}-9H-pyrido[3,4-b]indol-1-yl)propanoyl]pyrrolidine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 63 66  0  0  0  0  0  0  0  0999 V2000
   -6.7884   -2.1204   -2.5640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7760   -1.4482   -1.6722 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.2152   -0.6929   -2.7535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5689    0.6050   -0.9366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9296    1.3734    0.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9286    1.9214    0.9125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3926    1.7136    0.5863 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1542    2.3722    1.4957 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3717    2.9952    2.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6927    3.7885    3.4990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3284    4.3183    4.2666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6412    4.0324    3.8966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9575    3.2531    2.8106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9337    2.7230    2.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7492    0.9465   -0.5092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1773    0.7425   -0.8425 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8557   -0.2501    0.0596 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2859   -0.4359   -0.2940 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7281    0.2561   -1.2300 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1017   -1.3656    0.4141 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5957   -2.1762    1.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4402   -3.4127    1.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6874   -3.1018    0.8037 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4761   -1.7087    0.2598 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9934   -1.6663   -1.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2298   -1.5476   -2.0907 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3880   -1.7694   -1.2861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2655    0.4284   -1.2189 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.6321    1.7773   -2.8582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7893    0.2119   -3.9914 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.3590   -2.2720   -3.5790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0629   -3.1093   -2.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1206   -2.2112   -1.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7784   -0.3730    0.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4015   -1.0408   -3.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3926    0.7253   -0.7825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9794    1.5352    0.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2056    2.4199    1.5344 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7484    3.9776    3.7383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1010    4.9388    5.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4426    4.4582    4.5117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9577    3.0190    2.5065 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1925    0.3170   -1.8711 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6569    1.7566   -0.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8455    0.1569    1.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3059   -1.1955   -0.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5528   -2.4549    1.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7813   -1.6157    2.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6301   -3.7661    2.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9000   -4.2865    1.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7642   -3.7939   -0.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6168   -3.1895    1.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1138   -1.0432    0.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9591   -1.2078   -0.6665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4658   -0.2461   -4.8565 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 11 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 19 32  2  0
  4 33  1  0
 33 34  2  0
 33 35  1  0
 32  8  1  0
 18 10  1  0
 28 24  1  0
 18 13  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  1
  3 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  6
  5 44  1  0
  9 45  1  0
 12 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  0
 17 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 25 55  1  0
 25 56  1  0
 26 57  1  0
 26 58  1  0
 27 59  1  0
 27 60  1  0
 28 61  1  1
 31 62  1  0
 35 63  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      -6.788  -2.120  -2.564  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.776  -1.448  -1.672  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.493  -0.738  -0.518  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.949  -0.459  -2.449  0.00  0.00           C+0
HETATM    5  N   UNK     0      -3.975   0.174  -1.553  0.00  0.00           N+0
HETATM    6  C   UNK     0      -2.590   0.005  -1.781  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.215  -0.693  -2.753  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.569   0.605  -0.937  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.930   1.373   0.161  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.929   1.921   0.913  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.393   1.714   0.586  0.00  0.00           C+0
HETATM   12  N   UNK     0       1.154   2.372   1.496  0.00  0.00           N+0
HETATM   13  C   UNK     0       0.372   2.995   2.393  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.693   3.789   3.499  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.328   4.318   4.267  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.641   4.032   3.897  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.958   3.253   2.811  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.934   2.723   2.042  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.749   0.947  -0.509  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.177   0.743  -0.843  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.856  -0.250   0.060  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.286  -0.436  -0.294  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.728   0.256  -1.230  0.00  0.00           O+0
HETATM   24  N   UNK     0       5.102  -1.366   0.414  0.00  0.00           N+0
HETATM   25  C   UNK     0       4.596  -2.176   1.541  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.440  -3.413   1.537  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.687  -3.102   0.804  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.476  -1.709   0.260  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.993  -1.666  -1.136  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.230  -1.548  -2.091  0.00  0.00           O+0
HETATM   31  O   UNK     0       8.388  -1.769  -1.286  0.00  0.00           O+0
HETATM   32  N   UNK     0      -0.266   0.428  -1.219  0.00  0.00           N+0
HETATM   33  C   UNK     0      -5.790   0.554  -3.096  0.00  0.00           C+0
HETATM   34  O   UNK     0      -5.632   1.777  -2.858  0.00  0.00           O+0
HETATM   35  O   UNK     0      -6.789   0.212  -3.991  0.00  0.00           O+0
HETATM   36  H   UNK     0      -7.711  -1.519  -2.686  0.00  0.00           H+0
HETATM   37  H   UNK     0      -6.359  -2.272  -3.579  0.00  0.00           H+0
HETATM   38  H   UNK     0      -7.063  -3.109  -2.118  0.00  0.00           H+0
HETATM   39  H   UNK     0      -5.121  -2.211  -1.215  0.00  0.00           H+0
HETATM   40  H   UNK     0      -5.778  -0.373   0.240  0.00  0.00           H+0
HETATM   41  H   UNK     0      -7.037   0.152  -0.927  0.00  0.00           H+0
HETATM   42  H   UNK     0      -7.231  -1.431  -0.065  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.402  -1.041  -3.236  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.393   0.725  -0.783  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.979   1.535   0.419  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.206   2.420   1.534  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.748   3.978   3.738  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.101   4.939   5.131  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.443   4.458   4.512  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.958   3.019   2.506  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.192   0.317  -1.871  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.657   1.757  -0.820  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.845   0.157   1.092  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.306  -1.196  -0.032  0.00  0.00           H+0
HETATM   55  H   UNK     0       3.553  -2.455   1.393  0.00  0.00           H+0
HETATM   56  H   UNK     0       4.781  -1.616   2.491  0.00  0.00           H+0
HETATM   57  H   UNK     0       5.630  -3.766   2.594  0.00  0.00           H+0
HETATM   58  H   UNK     0       4.900  -4.287   1.070  0.00  0.00           H+0
HETATM   59  H   UNK     0       6.764  -3.794  -0.084  0.00  0.00           H+0
HETATM   60  H   UNK     0       7.617  -3.189   1.394  0.00  0.00           H+0
HETATM   61  H   UNK     0       7.114  -1.043   0.922  0.00  0.00           H+0
HETATM   62  H   UNK     0       8.959  -1.208  -0.667  0.00  0.00           H+0
HETATM   63  H   UNK     0      -6.466  -0.246  -4.856  0.00  0.00           H+0
CONECT    1    2   36   37   38                                             
CONECT    2    1    3    4   39                                             
CONECT    3    2   40   41   42                                             
CONECT    4    2    5   33   43                                             
CONECT    5    4    6   44                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   32                                                  
CONECT    9    8   10   45                                                  
CONECT   10    9   11   18                                                  
CONECT   11   10   12   19                                                  
CONECT   12   11   13   46                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15   47                                                  
CONECT   15   14   16   48                                                  
CONECT   16   15   17   49                                                  
CONECT   17   16   18   50                                                  
CONECT   18   17   10   13                                                  
CONECT   19   11   20   32                                                  
CONECT   20   19   21   51   52                                             
CONECT   21   20   22   53   54                                             
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   28                                                  
CONECT   25   24   26   55   56                                             
CONECT   26   25   27   57   58                                             
CONECT   27   26   28   59   60                                             
CONECT   28   27   29   24   61                                             
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   62                                                       
CONECT   32   19    8                                                       
CONECT   33    4   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   63                                                       
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    2                                                            
CONECT   40    3                                                            
CONECT   41    3                                                            
CONECT   42    3                                                            
CONECT   43    4                                                            
CONECT   44    5                                                            
CONECT   45    9                                                            
CONECT   46   12                                                            
CONECT   47   14                                                            
CONECT   48   15                                                            
CONECT   49   16                                                            
CONECT   50   17                                                            
CONECT   51   20                                                            
CONECT   52   20                                                            
CONECT   53   21                                                            
CONECT   54   21                                                            
CONECT   55   25                                                            
CONECT   56   25                                                            
CONECT   57   26                                                            
CONECT   58   26                                                            
CONECT   59   27                                                            
CONECT   60   27                                                            
CONECT   61   28                                                            
CONECT   62   31                                                            
CONECT   63   35                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  132    0
END

RDKit          3D

63 66  0  0  0  0  0  0  0  0999 V2000
   -6.7884   -2.1204   -2.5640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7760   -1.4482   -1.6722 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4931   -0.7380   -0.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9490   -0.4590   -2.4490 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9753    0.1739   -1.5534 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5900    0.0049   -1.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2152   -0.6929   -2.7535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5689    0.6050   -0.9366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9296    1.3734    0.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9286    1.9214    0.9125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3926    1.7136    0.5863 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1542    2.3722    1.4957 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3717    2.9952    2.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6927    3.7885    3.4990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3284    4.3183    4.2666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6412    4.0324    3.8966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9575    3.2531    2.8106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9337    2.7230    2.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7492    0.9465   -0.5092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1773    0.7425   -0.8425 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8557   -0.2501    0.0596 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2859   -0.4359   -0.2940 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7281    0.2561   -1.2300 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1017   -1.3656    0.4141 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5957   -2.1762    1.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4402   -3.4127    1.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6874   -3.1018    0.8037 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4761   -1.7087    0.2598 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9934   -1.6663   -1.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2298   -1.5476   -2.0907 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3880   -1.7694   -1.2861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2655    0.4284   -1.2189 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7902    0.5537   -3.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6321    1.7773   -2.8582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7893    0.2119   -3.9914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7109   -1.5187   -2.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3590   -2.2720   -3.5790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0629   -3.1093   -2.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1206   -2.2112   -1.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7784   -0.3730    0.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0374    0.1522   -0.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2307   -1.4305   -0.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4015   -1.0408   -3.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3926    0.7253   -0.7825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9794    1.5352    0.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2056    2.4199    1.5344 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7484    3.9776    3.7383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1010    4.9388    5.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4426    4.4582    4.5117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9577    3.0190    2.5065 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1925    0.3170   -1.8711 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6569    1.7566   -0.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8455    0.1569    1.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3059   -1.1955   -0.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5528   -2.4549    1.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7813   -1.6157    2.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6301   -3.7661    2.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9000   -4.2865    1.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7642   -3.7939   -0.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6168   -3.1895    1.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1138   -1.0432    0.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9591   -1.2078   -0.6665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4658   -0.2461   -4.8565 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 11 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 19 32  2  0
  4 33  1  0
 33 34  2  0
 33 35  1  0
 32  8  1  0
 18 10  1  0
 28 24  1  0
 18 13  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  1
  3 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  6
  5 44  1  0
  9 45  1  0
 12 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  0
 17 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 25 55  1  0
 25 56  1  0
 26 57  1  0
 26 58  1  0
 27 59  1  0
 27 60  1  0
 28 61  1  1
 31 62  1  0
 35 63  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2S)-1-[3-(3-{[(1S)-1-carboxy-2-methylpropyl]carbamoyl}-9H-pyrido[3,4-b]indol-1-yl)propanoyl]pyrrolidine-2-carboxylate	Generator

Chemical Formula

C₂₅H₂₈N₄O₆

Average Mass

480.5210 Da

Monoisotopic Mass

480.20088 Da

IUPAC Name

(2S)-1-[3-(3-{[(1S)-1-carboxy-2-methylpropyl]carbamoyl}-9H-pyrido[3,4-b]indol-1-yl)propanoyl]pyrrolidine-2-carboxylic acid

Traditional Name

(2S)-1-[3-(3-{[(1S)-1-carboxy-2-methylpropyl]carbamoyl}-9H-pyrido[3,4-b]indol-1-yl)propanoyl]pyrrolidine-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(C)[C@H](NC(=O)C1=NC(CCC(=O)N2CCC[C@H]2C(O)=O)=C2NC3=CC=CC=C3C2=C1)C(O)=O

InChI Identifier

InChI=1S/C25H28N4O6/c1-13(2)21(25(34)35)28-23(31)18-12-15-14-6-3-4-7-16(14)27-22(15)17(26-18)9-10-20(30)29-11-5-8-19(29)24(32)33/h3-4,6-7,12-13,19,21,27H,5,8-11H2,1-2H3,(H,28,31)(H,32,33)(H,34,35)/t19-,21-/m0/s1

InChI Key

VDVKKTJHKSSCRY-FPOVZHCZSA-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
Mycena metata	NPAtlas	23330951

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Harmala alkaloids

Sub Class

Not Available

Direct Parent

Harmala alkaloids

Alternative Parents

Substituents

Harman
Beta-carboline
N-acyl-alpha-amino acid
Valine or derivatives
Proline or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Pyridoindole
Alpha-amino acid or derivatives
Indole
Indole or derivatives
Pyridine carboxylic acid or derivatives
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine carboxylic acid
N-acylpyrrolidine
2-heteroaryl carboxamide
Pyridine
Benzenoid
Dicarboxylic acid or derivatives
Tertiary carboxylic acid amide
Pyrrolidine
Pyrrole
Heteroaromatic compound
Secondary carboxylic acid amide
Carboxamide group
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
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	1.68	ALOGPS
logP	1.96	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	3.5	ChemAxon
pKa (Strongest Basic)	0.52	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	152.69 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	124.96 m³·mol⁻¹	ChemAxon
Polarizability	51.42 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

NPAtlas ID

NPA005707

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

58917836

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71578964

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Metatacarboline F (NP0011441)

MOL for NP0011441 (Metatacarboline F)

3D MOL for NP0011441 (Metatacarboline F)

3D SDF for NP0011441 (Metatacarboline F)

3D-SDF for NP0011441 (Metatacarboline F)

PDB for NP0011441 (Metatacarboline F)

3D PDB for NP0011441 (Metatacarboline F)

SMILES for NP0011441 (Metatacarboline F)

INCHI for NP0011441 (Metatacarboline F)

Structure for NP0011441 (Metatacarboline F)

3D Structure for NP0011441 (Metatacarboline F)