NP-MRD: Showing NP-Card for (3s,6s)-3-benzyl-5-hydroxy-1-methyl-6-[(4-nitro-1h-indol-3-yl)methyl]-3,6-dihydropyrazin-2-one (NP0162756)

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Record Information

Version

2.0

Created at

2022-09-02 21:13:35 UTC

Updated at

2022-09-02 21:13:36 UTC

NP-MRD ID

NP0162756

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,6s)-3-benzyl-5-hydroxy-1-methyl-6-[(4-nitro-1h-indol-3-yl)methyl]-3,6-dihydropyrazin-2-one

Description

THAXTOMIN C 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. (3s,6s)-3-benzyl-5-hydroxy-1-methyl-6-[(4-nitro-1h-indol-3-yl)methyl]-3,6-dihydropyrazin-2-one is found in Streptomyces ipomoeae. (3s,6s)-3-benzyl-5-hydroxy-1-methyl-6-[(4-nitro-1h-indol-3-yl)methyl]-3,6-dihydropyrazin-2-one was first documented in 2012 (PMID: 22088193). Based on a literature review very few articles have been published on THAXTOMIN C (PMID: 25804187).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022223132D          

 29 32  0  0  1  0            999 V2000
    0.3739   -3.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -3.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400   -4.0623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371   -2.6646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3441   -2.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8961   -2.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7031   -2.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2551   -1.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0002   -0.9968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1932   -0.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6412   -1.4384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822   -1.8800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203   -0.9238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.9233   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  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  2  0  0  0  0
  7 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 25 29  2  0  0  0  0
 18 29  1  0  0  0  0
 21 29  1  0  0  0  0
M  CHG  2  26   1  28  -1
M  END

     RDKit          3D

 49 52  0  0  0  0  0  0  0  0999 V2000
   -0.0862    2.6781    2.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4552    1.7202    1.4406 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8504    1.6747    1.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4839    2.7606    1.1730 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000    0.3528    0.8393 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8038    0.5030    0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3833   -0.8258   -0.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2425   -1.3849    0.7828 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7733   -2.6269    0.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4603   -3.2982   -0.6606 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6107   -2.7523   -1.5938 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0792   -1.5138   -1.3263 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5620   -0.3849    0.0763 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3082   -0.2434    0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3673   -1.1420   -0.8422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4267    0.7815    0.7628 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3821    1.5635   -0.1088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3478    0.8149   -0.8887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0733    0.3714   -2.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1150   -0.3276   -2.6160 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0800   -0.3880   -1.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3314   -0.9792   -1.7050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1425   -0.8447   -0.6106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7283   -0.1483    0.4762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4478    0.4504    0.5018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1700    1.2233    1.6223 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.2115    1.8587    2.0944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0426    1.4418    2.2630 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.5954    0.3328   -0.5897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5705    2.1087    3.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8166    3.3703    1.9628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7467    3.2351    2.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7259   -0.0866    1.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7276    1.1273   -0.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4977    1.0560    0.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4738   -0.8398    1.6910 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4500   -3.0680    1.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9093   -4.2888   -0.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4009   -3.3217   -2.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4024   -1.0609   -2.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1062   -1.5596   -1.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0330    0.2209    1.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6647    2.0780   -0.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7674    2.4617    0.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1685    0.5764   -2.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2312   -0.8049   -3.5657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6561   -1.5413   -2.5967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1271   -1.2939   -0.6017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3703   -0.0364    1.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 29  2  0
 25 26  1  0
 26 28  1  0
 26 27  2  0
 16 14  1  0
 14 15  1  0
 14 13  2  0
 13  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
 29 18  1  0
 12  7  1  0
 29 21  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 16 42  1  1
 17 43  1  0
 17 44  1  0
 19 45  1  0
 20 46  1  0
 22 47  1  0
 23 48  1  0
 24 49  1  0
 15 41  1  0
  5 33  1  1
  6 34  1  0
  6 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  0
M  CHG  2  26   1  28  -1
M  END


  Mrv1652309022223132D          

 29 32  0  0  1  0            999 V2000
    0.3739   -3.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -3.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400   -4.0623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371   -2.6646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3441   -2.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8961   -2.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7031   -2.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2551   -1.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0002   -0.9968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1932   -0.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6412   -1.4384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822   -1.8800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203   -0.9238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.9233   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  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  2  0  0  0  0
  7 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 25 29  2  0  0  0  0
 18 29  1  0  0  0  0
 21 29  1  0  0  0  0
M  CHG  2  26   1  28  -1
M  END
> <DATABASE_ID>
NP0162756

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1[C@@H](CC2=CNC3=CC=CC(=C23)[N+]([O-])=O)C(O)=N[C@@H](CC2=CC=CC=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20N4O4/c1-24-18(11-14-12-22-15-8-5-9-17(19(14)15)25(28)29)20(26)23-16(21(24)27)10-13-6-3-2-4-7-13/h2-9,12,16,18,22H,10-11H2,1H3,(H,23,26)/t16-,18-/m0/s1

> <INCHI_KEY>
IAIWBAHUWORDTI-WMZOPIPTSA-N

> <FORMULA>
C21H20N4O4

> <MOLECULAR_WEIGHT>
392.415

> <EXACT_MASS>
392.14845514

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
39.46450025266216

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,6S)-3-benzyl-5-hydroxy-1-methyl-6-[(4-nitro-1H-indol-3-yl)methyl]-1,2,3,6-tetrahydropyrazin-2-one

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
3.321641115666666

> <ALOGPS_LOGS>
-4.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.978767823810138

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.333136027106573

> <JCHEM_PKA_STRONGEST_BASIC>
0.975057884080823

> <JCHEM_POLAR_SURFACE_AREA>
111.83000000000001

> <JCHEM_REFRACTIVITY>
106.65820000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.42e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6S)-3-benzyl-5-hydroxy-1-methyl-6-[(4-nitro-1H-indol-3-yl)methyl]-3,6-dihydropyrazin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       0.698  -6.943   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.333  -5.798   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -1.839  -6.118   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.315  -7.583   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.869  -4.974   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.376  -5.294   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.406  -4.150   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.912  -4.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -7.943  -3.325   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.467  -1.861   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.961  -1.541   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.930  -2.685   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -2.393  -3.509   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -0.887  -3.189   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.411  -1.724   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       4.924  -4.383   0.000  0.00  0.00           N+1
HETATM   27  O   UNK     0       3.590  -5.153   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       6.258  -5.153   0.000  0.00  0.00           O-1
HETATM   29  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13    5   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    2   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   29                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   29                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   29                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   25   18   21                                                  
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₀N₄O₄

Average Mass

392.4150 Da

Monoisotopic Mass

392.14846 Da

IUPAC Name

(3S,6S)-3-benzyl-5-hydroxy-1-methyl-6-[(4-nitro-1H-indol-3-yl)methyl]-1,2,3,6-tetrahydropyrazin-2-one

Traditional Name

(3S,6S)-3-benzyl-5-hydroxy-1-methyl-6-[(4-nitro-1H-indol-3-yl)methyl]-3,6-dihydropyrazin-2-one

CAS Registry Number

Not Available

SMILES

CN1[C@@H](CC2=CNC3=CC=CC(=C23)[N+]([O-])=O)C(O)=N[C@@H](CC2=CC=CC=C2)C1=O

InChI Identifier

InChI=1S/C21H20N4O4/c1-24-18(11-14-12-22-15-8-5-9-17(19(14)15)25(28)29)20(26)23-16(21(24)27)10-13-6-3-2-4-7-13/h2-9,12,16,18,22H,10-11H2,1H3,(H,23,26)/t16-,18-/m0/s1

InChI Key

IAIWBAHUWORDTI-WMZOPIPTSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Streptomyces ipomoeae	LOTUS Database	35616633

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
3-alkylindole
Indole
Indole or derivatives
Nitroaromatic compound
Dioxopiperazine
2,5-dioxopiperazine
N-alkylpiperazine
N-methylpiperazine
Monocyclic benzene moiety
1,4-diazinane
Benzenoid
Piperazine
Substituted pyrrole
Heteroaromatic compound
Tertiary carboxylic acid amide
Pyrrole
Carboxamide group
Organic nitro compound
Lactam
C-nitro compound
Secondary carboxylic acid amide
Organoheterocyclic compound
Organic oxoazanium
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic salt
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organic zwitterion
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	2.71	ALOGPS
logP	3.32	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	4.33	ChemAxon
pKa (Strongest Basic)	0.98	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	111.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	106.66 m³·mol⁻¹	ChemAxon
Polarizability	39.46 Å³	ChemAxon
Number of Rings	4	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9276392

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11101250

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang H, Wang Q, Ning X, Hang H, Ma J, Yang X, Lu X, Zhang J, Li Y, Niu C, Song H, Wang X, Wang PG: Synthesis and biological evaluations of a series of thaxtomin analogues. J Agric Food Chem. 2015 Apr 15;63(14):3734-41. doi: 10.1021/jf506153t. Epub 2015 Apr 3. [PubMed:25804187 ]
Guan D, Grau BL, Clark CA, Taylor CM, Loria R, Pettis GS: Evidence that thaxtomin C is a pathogenicity determinant of Streptomyces ipomoeae, the causative agent of Streptomyces soil rot disease of sweet potato. Mol Plant Microbe Interact. 2012 Mar;25(3):393-401. doi: 10.1094/MPMI-03-11-0073. [PubMed:22088193 ]
LOTUS database [Link]

Showing NP-Card for (3s,6s)-3-benzyl-5-hydroxy-1-methyl-6-[(4-nitro-1h-indol-3-yl)methyl]-3,6-dihydropyrazin-2-one (NP0162756)

MOL for NP0162756 ((3s,6s)-3-benzyl-5-hydroxy-1-methyl-6-[(4-nitro-1h-indol-3-yl)methyl]-3,6-dihydropyrazin-2-one)

3D MOL for NP0162756 ((3s,6s)-3-benzyl-5-hydroxy-1-methyl-6-[(4-nitro-1h-indol-3-yl)methyl]-3,6-dihydropyrazin-2-one)

3D SDF for NP0162756 ((3s,6s)-3-benzyl-5-hydroxy-1-methyl-6-[(4-nitro-1h-indol-3-yl)methyl]-3,6-dihydropyrazin-2-one)

3D-SDF for NP0162756 ((3s,6s)-3-benzyl-5-hydroxy-1-methyl-6-[(4-nitro-1h-indol-3-yl)methyl]-3,6-dihydropyrazin-2-one)

PDB for NP0162756 ((3s,6s)-3-benzyl-5-hydroxy-1-methyl-6-[(4-nitro-1h-indol-3-yl)methyl]-3,6-dihydropyrazin-2-one)

3D PDB for NP0162756 ((3s,6s)-3-benzyl-5-hydroxy-1-methyl-6-[(4-nitro-1h-indol-3-yl)methyl]-3,6-dihydropyrazin-2-one)

SMILES for NP0162756 ((3s,6s)-3-benzyl-5-hydroxy-1-methyl-6-[(4-nitro-1h-indol-3-yl)methyl]-3,6-dihydropyrazin-2-one)

INCHI for NP0162756 ((3s,6s)-3-benzyl-5-hydroxy-1-methyl-6-[(4-nitro-1h-indol-3-yl)methyl]-3,6-dihydropyrazin-2-one)

Structure for NP0162756 ((3s,6s)-3-benzyl-5-hydroxy-1-methyl-6-[(4-nitro-1h-indol-3-yl)methyl]-3,6-dihydropyrazin-2-one)

3D Structure for NP0162756 ((3s,6s)-3-benzyl-5-hydroxy-1-methyl-6-[(4-nitro-1h-indol-3-yl)methyl]-3,6-dihydropyrazin-2-one)