NP-MRD: Showing NP-Card for (3r,6s)-3-hydroxy-3-[(2-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1h-indol-3-yl)methyl]piperazine-2,5-dione (NP0174519)

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Record Information

Version

2.0

Created at

2022-09-03 11:47:09 UTC

Updated at

2022-09-03 11:47:09 UTC

NP-MRD ID

NP0174519

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,6s)-3-hydroxy-3-[(2-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1h-indol-3-yl)methyl]piperazine-2,5-dione

Description

O-thaxtomin A 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. Based on a literature review very few articles have been published on O-thaxtomin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032213472D          

 32 35  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
   -2.0451   -3.3147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2656   -2.2773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9652   -2.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9364   -3.5390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6361   -3.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3645   -3.5888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3933   -2.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6936   -2.3271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7224   -1.5026    0.0000 O   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
   -1.8342   -1.2669    0.0000 C   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  1  0  0  0
  5  7  1  6  0  0  0
  7  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  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  6  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  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  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
 28 32  2  0  0  0  0
 21 32  1  0  0  0  0
 24 32  1  0  0  0  0
M  CHG  2  29   1  31  -1
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
    0.1095   -1.0609    2.9759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4619   -1.0112    1.5678 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7585   -0.7084    1.1241 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5256   -0.1166    1.9375 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2251   -1.0512   -0.1985 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1866   -2.0917   -0.0248 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8844   -0.0043   -1.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9395    0.7919   -0.4286 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2650    0.3941   -0.5019 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2801    1.1265    0.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9869    2.2772    0.7675 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6866    2.6956    0.8576 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6710    1.9545    0.2619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3781    2.4173    0.3786 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1820   -1.6128   -1.0543 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5152   -2.4604   -2.1401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1744   -1.2283   -0.7421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9188   -0.8334   -1.6762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6224   -1.3104    0.6313 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8184   -0.4073    0.9931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9861   -0.6034    0.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2453   -1.6949   -0.6398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3724   -1.5215   -1.3273 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8840   -0.3072   -0.9945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0202    0.3335   -1.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3330    1.5860   -0.9582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5145    2.1765   -0.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3528    1.5444    0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6197    2.2241    1.3949 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.6317    3.4983    1.3265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8994    1.6967    2.3977 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.0375    0.3050   -0.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9865   -1.2997    3.6393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2733   -0.0734    3.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6842   -1.8330    3.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9149   -2.5855    0.7816 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2933   -0.5314   -1.9483 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0608    0.6182   -1.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5212   -0.5265   -1.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2823    0.7672   -0.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7570    2.8608    1.2363 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4765    3.6264    1.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6214    1.9259   -0.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8143   -3.2719   -2.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5207   -2.9347   -1.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5849   -1.8139   -3.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9722   -2.3351    0.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4002    0.6046    0.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9757   -0.6357    2.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6463   -2.5816   -0.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8421   -2.1550   -2.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7046   -0.1085   -2.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2251    2.1315   -1.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7355    3.1538    0.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 32  2  0
 28 29  1  0
 29 31  1  0
 29 30  2  0
 19 17  1  0
 17 18  2  0
 17 15  1  0
 15 16  1  0
 15  5  1  0
  5  6  1  1
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
 32 21  1  0
 13  8  1  0
 32 24  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
 19 47  1  1
 20 48  1  0
 20 49  1  0
 22 50  1  0
 23 51  1  0
 25 52  1  0
 26 53  1  0
 27 54  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
  6 36  1  0
  7 37  1  0
  7 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 12 42  1  0
 14 43  1  0
M  CHG  2  29   1  31  -1
M  END


  Mrv1652309032213472D          

 32 35  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
   -2.0451   -3.3147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2656   -2.2773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9652   -2.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9364   -3.5390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6361   -3.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3645   -3.5888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3933   -2.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6936   -2.3271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7224   -1.5026    0.0000 O   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
   -1.8342   -1.2669    0.0000 C   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  1  0  0  0
  5  7  1  6  0  0  0
  7  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  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  6  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  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  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
 28 32  2  0  0  0  0
 21 32  1  0  0  0  0
 24 32  1  0  0  0  0
M  CHG  2  29   1  31  -1
M  END
> <DATABASE_ID>
NP0174519

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1[C@@H](CC2=CNC3=CC=CC(=C23)[N+]([O-])=O)C(=O)N(C)[C@@](O)(CC2=CC=CC=C2O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H22N4O6/c1-24-17(10-14-12-23-15-7-5-8-16(19(14)15)26(31)32)20(28)25(2)22(30,21(24)29)11-13-6-3-4-9-18(13)27/h3-9,12,17,23,27,30H,10-11H2,1-2H3/t17-,22+/m0/s1

> <INCHI_KEY>
XNRUYCJWMXPFHD-HTAPYJJXSA-N

> <FORMULA>
C22H22N4O6

> <MOLECULAR_WEIGHT>
438.44

> <EXACT_MASS>
438.153934444

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
42.109347627393845

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,6S)-3-hydroxy-3-[(2-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1H-indol-3-yl)methyl]piperazine-2,5-dione

> <ALOGPS_LOGP>
2.29

> <JCHEM_LOGP>
2.155951442666666

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.104105402934998

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.3167691327647

> <JCHEM_PKA_STRONGEST_BASIC>
-4.529828871682725

> <JCHEM_POLAR_SURFACE_AREA>
140.01000000000002

> <JCHEM_REFRACTIVITY>
114.6669

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,6S)-3-hydroxy-3-[(2-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1H-indol-3-yl)methyl]piperazine-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-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  O   UNK     0      -3.817  -6.187   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -4.229  -4.251   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.535  -5.067   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.481  -6.606   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.787  -7.422   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.147  -6.699   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.201  -5.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.895  -4.344   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -6.949  -2.805   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0      -2.393  -3.509   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      -3.424  -2.365   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.887  -3.189   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.411  -1.724   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       4.924  -4.383   0.000  0.00  0.00           N+1
HETATM   30  O   UNK     0       3.590  -5.153   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       6.258  -5.153   0.000  0.00  0.00           O-1
HETATM   32  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   15                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13                                                            
CONECT   15    5   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    2   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   32                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   32                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   28   21   24                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₂N₄O₆

Average Mass

438.4400 Da

Monoisotopic Mass

438.15393 Da

IUPAC Name

(3R,6S)-3-hydroxy-3-[(2-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1H-indol-3-yl)methyl]piperazine-2,5-dione

Traditional Name

(3R,6S)-3-hydroxy-3-[(2-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1H-indol-3-yl)methyl]piperazine-2,5-dione

CAS Registry Number

Not Available

SMILES

CN1[C@@H](CC2=CNC3=CC=CC(=C23)[N+]([O-])=O)C(=O)N(C)[C@@](O)(CC2=CC=CC=C2O)C1=O

InChI Identifier

InChI=1S/C22H22N4O6/c1-24-17(10-14-12-23-15-7-5-8-16(19(14)15)26(31)32)20(28)25(2)22(30,21(24)29)11-13-6-3-4-9-18(13)27/h3-9,12,17,23,27,30H,10-11H2,1-2H3/t17-,22+/m0/s1

InChI Key

XNRUYCJWMXPFHD-HTAPYJJXSA-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

Not Available

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
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
N-alkylpiperazine
N-methylpiperazine
Phenol
Monocyclic benzene moiety
1,4-diazinane
Benzenoid
Piperazine
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Tertiary carboxylic acid amide
Carboxamide group
Organic nitro compound
Lactam
C-nitro compound
Allyl-type 1,3-dipolar organic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Alkanolamine
Azacycle
Organic oxoazanium
Organoheterocyclic compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organic zwitterion
Organonitrogen compound
Organooxygen compound
Organic oxide
Organic salt
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	2.29	ALOGPS
logP	2.16	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	9.32	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	140.01 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	114.67 m³·mol⁻¹	ChemAxon
Polarizability	42.11 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

31143619

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76326879

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r,6s)-3-hydroxy-3-[(2-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1h-indol-3-yl)methyl]piperazine-2,5-dione (NP0174519)

MOL for NP0174519 ((3r,6s)-3-hydroxy-3-[(2-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1h-indol-3-yl)methyl]piperazine-2,5-dione)

3D MOL for NP0174519 ((3r,6s)-3-hydroxy-3-[(2-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1h-indol-3-yl)methyl]piperazine-2,5-dione)

3D SDF for NP0174519 ((3r,6s)-3-hydroxy-3-[(2-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1h-indol-3-yl)methyl]piperazine-2,5-dione)

3D-SDF for NP0174519 ((3r,6s)-3-hydroxy-3-[(2-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1h-indol-3-yl)methyl]piperazine-2,5-dione)

PDB for NP0174519 ((3r,6s)-3-hydroxy-3-[(2-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1h-indol-3-yl)methyl]piperazine-2,5-dione)

3D PDB for NP0174519 ((3r,6s)-3-hydroxy-3-[(2-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1h-indol-3-yl)methyl]piperazine-2,5-dione)

SMILES for NP0174519 ((3r,6s)-3-hydroxy-3-[(2-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1h-indol-3-yl)methyl]piperazine-2,5-dione)

INCHI for NP0174519 ((3r,6s)-3-hydroxy-3-[(2-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1h-indol-3-yl)methyl]piperazine-2,5-dione)

Structure for NP0174519 ((3r,6s)-3-hydroxy-3-[(2-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1h-indol-3-yl)methyl]piperazine-2,5-dione)

3D Structure for NP0174519 ((3r,6s)-3-hydroxy-3-[(2-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1h-indol-3-yl)methyl]piperazine-2,5-dione)