NP-MRD: Showing NP-Card for (-)-Phenylahistin (NP0001631)

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Record Information

Version

2.0

Created at

2020-09-23 01:59:24 UTC

Updated at

2021-08-10 02:55:51 UTC

NP-MRD ID

NP0001631

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Phenylahistin

Provided By

NPAtlas

Description

(3S,6Z)-3-benzyl-6-{[5-(2-methylbut-3-en-2-yl)-1H-imidazol-4-yl]methylidene}-3,6-dihydropyrazine-2,5-diol belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. (-)-Phenylahistin is found in Aspergillus. (-)-Phenylahistin was first documented in 1999 (PMID: 10344567). Based on a literature review very few articles have been published on (3S,6Z)-3-benzyl-6-{[5-(2-methylbut-3-en-2-yl)-1H-imidazol-4-yl]methylidene}-3,6-dihydropyrazine-2,5-diol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117443D          

 48 50  0  0  0  0            999 V2000
    6.3105   -0.1461    1.6712 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5949   -0.8034    0.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4106   -0.1520    0.1819 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7915    1.2218   -0.2758 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9427   -0.9185   -1.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3098   -0.1453    1.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4292   -0.6662    2.4118 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2881   -0.5207    3.0755 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4268    0.0988    2.2691 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0278    0.3396    1.1050 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5133    1.0123   -0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3122    0.7391   -0.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5720   -0.1955    0.0992 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9002   -0.4393   -0.4296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3739   -1.5776   -0.2035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5084    0.6610   -1.1501 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8281    0.4714   -1.7694 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9464    0.1208   -0.9022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6573    1.1022   -0.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7256    0.7766    0.5617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1030   -0.5373    0.7353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4103   -1.5300    0.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3289   -1.1804   -0.7237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5200    1.1279   -2.1331 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2187    1.4319   -1.6970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5301    2.2641   -2.2619 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0505    0.8554    1.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8460   -1.8101    0.5032 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3846    1.4397   -1.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5670    2.0196    0.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9052    1.2358   -0.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8968   -0.6166   -1.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6966   -0.2904   -2.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.4190    2.1678   -0.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3099    1.5321    1.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9537   -0.7732    1.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8388   -2.0052   -1.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7462    1.2421   -3.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
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  7 36  1  0  0  0  0
  8 37  1  0  0  0  0
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 13 39  1  0  0  0  0
 16 40  1  1  0  0  0
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 21 45  1  0  0  0  0
 22 46  1  0  0  0  0
 23 47  1  0  0  0  0
 24 48  1  0  0  0  0
M  END

     RDKit          3D

 48 50  0  0  0  0  0  0  0  0999 V2000
    6.3105   -0.1461    1.6712 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5949   -0.8034    0.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4106   -0.1520    0.1819 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7915    1.2218   -0.2758 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9427   -0.9185   -1.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3098   -0.1453    1.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2881   -0.5207    3.0755 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5133    1.0123   -0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.6573    1.1022   -0.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7256    0.7766    0.5617 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1682   -0.6105    2.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8460   -1.8101    0.5032 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306242117443D          

 48 50  0  0  0  0            999 V2000
    6.3105   -0.1461    1.6712 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5949   -0.8034    0.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3098   -0.1453    1.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
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 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 16 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 10  6  2  0  0  0  0
 25 12  1  0  0  0  0
 23 18  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  2 29  1  0  0  0  0
  4 30  1  0  0  0  0
  4 31  1  0  0  0  0
  4 32  1  0  0  0  0
  5 33  1  0  0  0  0
  5 34  1  0  0  0  0
  5 35  1  0  0  0  0
  7 36  1  0  0  0  0
  8 37  1  0  0  0  0
 11 38  1  0  0  0  0
 13 39  1  0  0  0  0
 16 40  1  1  0  0  0
 17 41  1  0  0  0  0
 17 42  1  0  0  0  0
 19 43  1  0  0  0  0
 20 44  1  0  0  0  0
 21 45  1  0  0  0  0
 22 46  1  0  0  0  0
 23 47  1  0  0  0  0
 24 48  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001631

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])=C([H])C(C1=C(N=C([H])N1[H])C(\[H])=C1/N([H])C(=O)[C@@]([H])(N([H])C1=O)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H22N4O2/c1-4-20(2,3)17-14(21-12-22-17)11-16-19(26)23-15(18(25)24-16)10-13-8-6-5-7-9-13/h4-9,11-12,15H,1,10H2,2-3H3,(H,21,22)(H,23,26)(H,24,25)/b16-11-/t15-/m0/s1

> <INCHI_KEY>
GWMHBVLPNWHWGW-CNYBTUBUSA-N

> <FORMULA>
C20H22N4O2

> <MOLECULAR_WEIGHT>
350.422

> <EXACT_MASS>
350.174275964

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
38.47978542992728

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,6Z)-3-benzyl-6-{[5-(2-methylbut-3-en-2-yl)-1H-imidazol-4-yl]methylidene}piperazine-2,5-dione

> <ALOGPS_LOGP>
2.55

> <JCHEM_LOGP>
1.8630765133333331

> <ALOGPS_LOGS>
-4.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.322497503508998

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.305047555637833

> <JCHEM_PKA_STRONGEST_BASIC>
5.745798230242831

> <JCHEM_POLAR_SURFACE_AREA>
86.88

> <JCHEM_REFRACTIVITY>
101.09750000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.10e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6Z)-3-benzyl-6-{[5-(2-methylbut-3-en-2-yl)-1H-imidazol-4-yl]methylidene}piperazine-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 48 50  0  0  0  0  0  0  0  0999 V2000
    6.3105   -0.1461    1.6712 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5949   -0.8034    0.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4106   -0.1520    0.1819 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7915    1.2218   -0.2758 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9427   -0.9185   -1.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3098   -0.1453    1.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4292   -0.6662    2.4118 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2881   -0.5207    3.0755 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4268    0.0988    2.2691 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0278    0.3396    1.1050 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5133    1.0123   -0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3122    0.7391   -0.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5720   -0.1955    0.0992 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9002   -0.4393   -0.4296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3739   -1.5776   -0.2035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5084    0.6610   -1.1501 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8281    0.4714   -1.7694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9464    0.1208   -0.9022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6573    1.1022   -0.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7256    0.7766    0.5617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1030   -0.5373    0.7353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4103   -1.5300    0.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3289   -1.1804   -0.7237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5200    1.1279   -2.1331 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2187    1.4319   -1.6970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5301    2.2641   -2.2619 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0505    0.8554    1.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1682   -0.6105    2.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8460   -1.8101    0.5032 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3846    1.4397   -1.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5670    2.0196    0.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9052    1.2358   -0.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8968   -0.6166   -1.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9955   -2.0260   -0.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5523   -0.5890   -1.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2800   -1.1353    2.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1161   -0.8615    4.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1068    1.7528   -0.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2505   -0.7249    0.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5940    1.5282   -0.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6966   -0.2904   -2.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1448    1.3937   -2.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4190    2.1678   -0.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3099    1.5321    1.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9537   -0.7732    1.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7103   -2.5477    0.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8388   -2.0052   -1.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7462    1.2421   -3.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  1
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 16 24  1  0
 24 25  1  0
 25 26  2  0
 10  6  2  0
 25 12  1  0
 23 18  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  4 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  5 35  1  0
  7 36  1  0
  8 37  1  0
 11 38  1  0
 13 39  1  0
 16 40  1  1
 17 41  1  0
 17 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  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       6.311  -0.146   1.671  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.595  -0.803   0.793  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.411  -0.152   0.182  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.792   1.222  -0.276  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.943  -0.919  -1.046  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.310  -0.145   1.184  0.00  0.00           C+0
HETATM    7  N   UNK     0       3.429  -0.666   2.412  0.00  0.00           N+0
HETATM    8  C   UNK     0       2.288  -0.521   3.075  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.427   0.099   2.269  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.028   0.340   1.105  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.513   1.012  -0.076  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.312   0.739  -0.506  0.00  0.00           C+0
HETATM   13  N   UNK     0      -0.572  -0.196   0.099  0.00  0.00           N+0
HETATM   14  C   UNK     0      -1.900  -0.439  -0.430  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.374  -1.578  -0.204  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.508   0.661  -1.150  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.828   0.471  -1.769  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.946   0.121  -0.902  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.657   1.102  -0.250  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.726   0.777   0.562  0.00  0.00           C+0
HETATM   21  C   UNK     0      -7.103  -0.537   0.735  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.410  -1.530   0.096  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.329  -1.180  -0.724  0.00  0.00           C+0
HETATM   24  N   UNK     0      -1.520   1.128  -2.133  0.00  0.00           N+0
HETATM   25  C   UNK     0      -0.219   1.432  -1.697  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.530   2.264  -2.262  0.00  0.00           O+0
HETATM   27  H   UNK     0       6.051   0.855   1.952  0.00  0.00           H+0
HETATM   28  H   UNK     0       7.168  -0.611   2.124  0.00  0.00           H+0
HETATM   29  H   UNK     0       5.846  -1.810   0.503  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.385   1.440  -1.287  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.567   2.020   0.452  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.905   1.236  -0.415  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.897  -0.617  -1.238  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.995  -2.026  -0.887  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.552  -0.589  -1.901  0.00  0.00           H+0
HETATM   36  H   UNK     0       4.280  -1.135   2.842  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.116  -0.862   4.107  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.107   1.753  -0.625  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.251  -0.725   0.943  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.594   1.528  -0.425  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.697  -0.290  -2.598  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.145   1.394  -2.341  0.00  0.00           H+0
HETATM   43  H   UNK     0      -5.419   2.168  -0.338  0.00  0.00           H+0
HETATM   44  H   UNK     0      -7.310   1.532   1.096  0.00  0.00           H+0
HETATM   45  H   UNK     0      -7.954  -0.773   1.384  0.00  0.00           H+0
HETATM   46  H   UNK     0      -6.710  -2.548   0.237  0.00  0.00           H+0
HETATM   47  H   UNK     0      -4.839  -2.005  -1.201  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.746   1.242  -3.140  0.00  0.00           H+0
CONECT    1    2   27   28                                                  
CONECT    2    1    3   29                                                  
CONECT    3    2    4    5    6                                             
CONECT    4    3   30   31   32                                             
CONECT    5    3   33   34   35                                             
CONECT    6    3    7   10                                                  
CONECT    7    6    8   36                                                  
CONECT    8    7    9   37                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11    6                                                  
CONECT   11   10   12   38                                                  
CONECT   12   11   13   25                                                  
CONECT   13   12   14   39                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   24   40                                             
CONECT   17   16   18   41   42                                             
CONECT   18   17   19   23                                                  
CONECT   19   18   20   43                                                  
CONECT   20   19   21   44                                                  
CONECT   21   20   22   45                                                  
CONECT   22   21   23   46                                                  
CONECT   23   22   18   47                                                  
CONECT   24   16   25   48                                                  
CONECT   25   24   26   12                                                  
CONECT   26   25                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    2                                                            
CONECT   30    4                                                            
CONECT   31    4                                                            
CONECT   32    4                                                            
CONECT   33    5                                                            
CONECT   34    5                                                            
CONECT   35    5                                                            
CONECT   36    7                                                            
CONECT   37    8                                                            
CONECT   38   11                                                            
CONECT   39   13                                                            
CONECT   40   16                                                            
CONECT   41   17                                                            
CONECT   42   17                                                            
CONECT   43   19                                                            
CONECT   44   20                                                            
CONECT   45   21                                                            
CONECT   46   22                                                            
CONECT   47   23                                                            
CONECT   48   24                                                            
MASTER        0    0    0    0    0    0    0    0   48    0  100    0
END

RDKit          3D

48 50  0  0  0  0  0  0  0  0999 V2000
    6.3105   -0.1461    1.6712 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5949   -0.8034    0.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4106   -0.1520    0.1819 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7915    1.2218   -0.2758 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9427   -0.9185   -1.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3098   -0.1453    1.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4292   -0.6662    2.4118 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2881   -0.5207    3.0755 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4268    0.0988    2.2691 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0278    0.3396    1.1050 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5133    1.0123   -0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3122    0.7391   -0.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5720   -0.1955    0.0992 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9002   -0.4393   -0.4296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3739   -1.5776   -0.2035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5084    0.6610   -1.1501 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8281    0.4714   -1.7694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9464    0.1208   -0.9022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6573    1.1022   -0.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7256    0.7766    0.5617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1030   -0.5373    0.7353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4103   -1.5300    0.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3289   -1.1804   -0.7237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5200    1.1279   -2.1331 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2187    1.4319   -1.6970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5301    2.2641   -2.2619 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0505    0.8554    1.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1682   -0.6105    2.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8460   -1.8101    0.5032 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3846    1.4397   -1.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5670    2.0196    0.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9052    1.2358   -0.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8968   -0.6166   -1.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9955   -2.0260   -0.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5523   -0.5890   -1.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2800   -1.1353    2.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1161   -0.8615    4.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1068    1.7528   -0.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2505   -0.7249    0.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5940    1.5282   -0.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6966   -0.2904   -2.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1448    1.3937   -2.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4190    2.1678   -0.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3099    1.5321    1.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9537   -0.7732    1.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7103   -2.5477    0.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8388   -2.0052   -1.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7462    1.2421   -3.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  1
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 16 24  1  0
 24 25  1  0
 25 26  2  0
 10  6  2  0
 25 12  1  0
 23 18  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  4 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  5 35  1  0
  7 36  1  0
  8 37  1  0
 11 38  1  0
 13 39  1  0
 16 40  1  1
 17 41  1  0
 17 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₀H₂₂N₄O₂

Average Mass

350.4220 Da

Monoisotopic Mass

350.17428 Da

IUPAC Name

(3S,6Z)-3-benzyl-6-{[5-(2-methylbut-3-en-2-yl)-1H-imidazol-4-yl]methylidene}piperazine-2,5-dione

Traditional Name

(3S,6Z)-3-benzyl-6-{[5-(2-methylbut-3-en-2-yl)-1H-imidazol-4-yl]methylidene}piperazine-2,5-dione

CAS Registry Number

Not Available

SMILES

[H]C([H])=C([H])C(C1=C(N=C([H])N1[H])C(\[H])=C1/N([H])C(=O)[C@@]([H])(N([H])C1=O)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C20H22N4O2/c1-4-20(2,3)17-14(21-12-22-17)11-16-19(26)23-15(18(25)24-16)10-13-8-6-5-7-9-13/h4-9,11-12,15H,1,10H2,2-3H3,(H,21,22)(H,23,26)(H,24,25)/b16-11-/t15-/m0/s1

InChI Key

GWMHBVLPNWHWGW-CNYBTUBUSA-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
Aspergillus	NPAtlas	10344567

Species Where Detected

Species Name	Source	Reference
Aspergillus ustus	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Dioxopiperazine
2,5-dioxopiperazine
Monocyclic benzene moiety
1,4-diazinane
Benzenoid
Piperazine
Azole
Heteroaromatic compound
Imidazole
Carboxamide group
Secondary carboxylic acid amide
Lactam
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	2.55	ALOGPS
logP	1.86	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	11.31	ChemAxon
pKa (Strongest Basic)	5.75	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.88 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	101.1 m³·mol⁻¹	ChemAxon
Polarizability	38.48 Å³	ChemAxon
Number of Rings	3	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

NPA015627

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

7974262

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9798496

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kanoh K, Kohno S, Katada J, Takahashi J, Uno I: (-)-Phenylahistin arrests cells in mitosis by inhibiting tubulin polymerization. J Antibiot (Tokyo). 1999 Feb;52(2):134-41. doi: 10.7164/antibiotics.52.134. [PubMed:10344567 ]

Showing NP-Card for (-)-Phenylahistin (NP0001631)

MOL for NP0001631 ((-)-Phenylahistin)

3D MOL for NP0001631 ((-)-Phenylahistin)

3D SDF for NP0001631 ((-)-Phenylahistin)

3D-SDF for NP0001631 ((-)-Phenylahistin)

PDB for NP0001631 ((-)-Phenylahistin)

3D PDB for NP0001631 ((-)-Phenylahistin)

SMILES for NP0001631 ((-)-Phenylahistin)

INCHI for NP0001631 ((-)-Phenylahistin)

Structure for NP0001631 ((-)-Phenylahistin)

3D Structure for NP0001631 ((-)-Phenylahistin)