NP-MRD: Showing NP-Card for N-(2,3-dibromo-4,5-dihydroxybenzyl)methyl pyroglutamate (NP0028121)

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Record Information

Version

2.0

Created at

2021-06-19 20:05:40 UTC

Updated at

2021-06-29 23:54:41 UTC

NP-MRD ID

NP0028121

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-(2,3-dibromo-4,5-dihydroxybenzyl)methyl pyroglutamate

Provided By

JEOL Database JEOL Logo

Description

N-(2,3-dibromo-4,5-dihydroxybenzyl)methyl pyroglutamate is found in Rhodomela confervoides. N-(2,3-dibromo-4,5-dihydroxybenzyl)methyl pyroglutamate was first documented in 2005 (Zhao, J., et al.). Based on a literature review very few articles have been published on methyl (2R)-1-[(2,3-dibromo-4,5-dihydroxyphenyl)methyl]-5-oxopyrrolidine-2-carboxylate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122053D          

 34 35  0  0  0  0            999 V2000
   -2.5575    3.3608   -0.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4997    1.9468   -0.4158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6551    1.5485    0.5742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9956    2.3102    1.2728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6299    0.0214    0.7400 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1995   -0.3612    2.1023 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6807   -0.5998    1.8242 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6824   -1.0913    0.3992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6087   -1.6635   -0.1491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4697   -0.7433   -0.1696 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1281   -0.9923   -1.5591 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9517   -1.9342   -1.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1928   -3.2960   -1.4208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1665   -4.2218   -1.5100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4310   -5.5329   -1.2398 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1161   -3.8285   -1.8674 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0665   -4.8174   -1.9303 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917   -2.4852   -2.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1836   -2.0329   -2.6136 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.3571   -1.5298   -2.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7223    0.3165   -2.3922 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9291    3.8542    0.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5735    3.7502   -0.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2548    3.5637   -1.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5911   -0.3088    0.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7423   -1.3002    2.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0439    0.3877    2.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2564    0.3292    1.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1055   -1.3475    2.4982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9900   -1.4429   -2.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9754   -0.0336   -2.0582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1888   -3.6341   -1.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4205   -5.9970   -1.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9056   -4.3952   -2.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 20  2  0  0  0  0
 20 18  1  0  0  0  0
 10  8  1  0  0  0  0
 12 11  1  0  0  0  0
 11 10  1  0  0  0  0
  5  3  1  0  0  0  0
 18 16  2  0  0  0  0
  3  4  2  0  0  0  0
  8  7  1  0  0  0  0
  3  2  1  0  0  0  0
 16 14  1  0  0  0  0
  8  9  2  0  0  0  0
  7  6  1  0  0  0  0
 14 15  1  0  0  0  0
 14 13  2  0  0  0  0
 16 17  1  0  0  0  0
  6  5  1  0  0  0  0
 18 19  1  0  0  0  0
 13 12  1  0  0  0  0
 20 21  1  0  0  0  0
  5 10  1  0  0  0  0
  2  1  1  0  0  0  0
  7 28  1  0  0  0  0
  7 29  1  0  0  0  0
  6 26  1  0  0  0  0
  6 27  1  0  0  0  0
  5 25  1  0  0  0  0
 13 32  1  0  0  0  0
 11 30  1  0  0  0  0
 11 31  1  0  0  0  0
 15 33  1  0  0  0  0
 17 34  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
M  END

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
   -2.5575    3.3608   -0.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4997    1.9468   -0.4158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6551    1.5485    0.5742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9956    2.3102    1.2728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6299    0.0214    0.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1995   -0.3612    2.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6807   -0.5998    1.8242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6824   -1.0913    0.3992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6087   -1.6635   -0.1491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4697   -0.7433   -0.1696 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1281   -0.9923   -1.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9517   -1.9342   -1.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1928   -3.2960   -1.4208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1665   -4.2218   -1.5100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4310   -5.5329   -1.2398 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1161   -3.8285   -1.8674 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0665   -4.8174   -1.9303 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917   -2.4852   -2.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1836   -2.0329   -2.6136 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.3571   -1.5298   -2.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7223    0.3165   -2.3922 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9291    3.8542    0.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5735    3.7502   -0.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2548    3.5637   -1.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5911   -0.3088    0.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7423   -1.3002    2.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0439    0.3877    2.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2564    0.3292    1.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1055   -1.3475    2.4982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9900   -1.4429   -2.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9754   -0.0336   -2.0582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1888   -3.6341   -1.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4205   -5.9970   -1.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9056   -4.3952   -2.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 20  2  0
 20 18  1  0
 10  8  1  0
 12 11  1  0
 11 10  1  0
  5  3  1  0
 18 16  2  0
  3  4  2  0
  8  7  1  0
  3  2  1  0
 16 14  1  0
  8  9  2  0
  7  6  1  0
 14 15  1  0
 14 13  2  0
 16 17  1  0
  6  5  1  0
 18 19  1  0
 13 12  1  0
 20 21  1  0
  5 10  1  0
  2  1  1  0
  7 28  1  0
  7 29  1  0
  6 26  1  0
  6 27  1  0
  5 25  1  0
 13 32  1  0
 11 30  1  0
 11 31  1  0
 15 33  1  0
 17 34  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
M  END


  Mrv1652306192122053D          

 34 35  0  0  0  0            999 V2000
   -2.5575    3.3608   -0.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4997    1.9468   -0.4158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6551    1.5485    0.5742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9956    2.3102    1.2728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6299    0.0214    0.7400 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1995   -0.3612    2.1023 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6807   -0.5998    1.8242 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6824   -1.0913    0.3992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6087   -1.6635   -0.1491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4697   -0.7433   -0.1696 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1281   -0.9923   -1.5591 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9517   -1.9342   -1.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1928   -3.2960   -1.4208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1665   -4.2218   -1.5100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4310   -5.5329   -1.2398 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1161   -3.8285   -1.8674 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0665   -4.8174   -1.9303 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917   -2.4852   -2.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1836   -2.0329   -2.6136 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.3571   -1.5298   -2.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7223    0.3165   -2.3922 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9291    3.8542    0.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5735    3.7502   -0.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2548    3.5637   -1.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5911   -0.3088    0.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7423   -1.3002    2.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0439    0.3877    2.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2564    0.3292    1.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1055   -1.3475    2.4982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9900   -1.4429   -2.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9754   -0.0336   -2.0582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1888   -3.6341   -1.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4205   -5.9970   -1.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9056   -4.3952   -2.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 20  2  0  0  0  0
 20 18  1  0  0  0  0
 10  8  1  0  0  0  0
 12 11  1  0  0  0  0
 11 10  1  0  0  0  0
  5  3  1  0  0  0  0
 18 16  2  0  0  0  0
  3  4  2  0  0  0  0
  8  7  1  0  0  0  0
  3  2  1  0  0  0  0
 16 14  1  0  0  0  0
  8  9  2  0  0  0  0
  7  6  1  0  0  0  0
 14 15  1  0  0  0  0
 14 13  2  0  0  0  0
 16 17  1  0  0  0  0
  6  5  1  0  0  0  0
 18 19  1  0  0  0  0
 13 12  1  0  0  0  0
 20 21  1  0  0  0  0
  5 10  1  0  0  0  0
  2  1  1  0  0  0  0
  7 28  1  0  0  0  0
  7 29  1  0  0  0  0
  6 26  1  0  0  0  0
  6 27  1  0  0  0  0
  5 25  1  0  0  0  0
 13 32  1  0  0  0  0
 11 30  1  0  0  0  0
 11 31  1  0  0  0  0
 15 33  1  0  0  0  0
 17 34  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0028121

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(=C(Br)C(Br)=C1O[H])C([H])([H])N1C(=O)C([H])([H])C([H])([H])[C@]1([H])C(=O)OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C13H13Br2NO5/c1-21-13(20)7-2-3-9(18)16(7)5-6-4-8(17)12(19)11(15)10(6)14/h4,7,17,19H,2-3,5H2,1H3/t7-/m1/s1

> <INCHI_KEY>
ARCCBVHXHHINEZ-SSDOTTSWSA-N

> <FORMULA>
C13H13Br2NO5

> <MOLECULAR_WEIGHT>
423.057

> <EXACT_MASS>
420.916049

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
32.37598917256439

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2R)-1-[(2,3-dibromo-4,5-dihydroxyphenyl)methyl]-5-oxopyrrolidine-2-carboxylate

> <ALOGPS_LOGP>
2.74

> <JCHEM_LOGP>
2.1347481439999996

> <ALOGPS_LOGS>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.307463580268367

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.537815244310784

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0295285773952663

> <JCHEM_POLAR_SURFACE_AREA>
87.07000000000001

> <JCHEM_REFRACTIVITY>
81.57360000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.73e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2R)-1-[(2,3-dibromo-4,5-dihydroxyphenyl)methyl]-5-oxopyrrolidine-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
   -2.5575    3.3608   -0.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4997    1.9468   -0.4158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6551    1.5485    0.5742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9956    2.3102    1.2728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6299    0.0214    0.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1995   -0.3612    2.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6807   -0.5998    1.8242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6824   -1.0913    0.3992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6087   -1.6635   -0.1491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4697   -0.7433   -0.1696 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1281   -0.9923   -1.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9517   -1.9342   -1.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1928   -3.2960   -1.4208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1665   -4.2218   -1.5100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4310   -5.5329   -1.2398 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1161   -3.8285   -1.8674 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0665   -4.8174   -1.9303 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917   -2.4852   -2.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1836   -2.0329   -2.6136 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.3571   -1.5298   -2.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7223    0.3165   -2.3922 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9291    3.8542    0.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5735    3.7502   -0.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2548    3.5637   -1.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5911   -0.3088    0.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7423   -1.3002    2.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0439    0.3877    2.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2564    0.3292    1.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1055   -1.3475    2.4982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9900   -1.4429   -2.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9754   -0.0336   -2.0582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1888   -3.6341   -1.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4205   -5.9970   -1.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9056   -4.3952   -2.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 20  2  0
 20 18  1  0
 10  8  1  0
 12 11  1  0
 11 10  1  0
  5  3  1  0
 18 16  2  0
  3  4  2  0
  8  7  1  0
  3  2  1  0
 16 14  1  0
  8  9  2  0
  7  6  1  0
 14 15  1  0
 14 13  2  0
 16 17  1  0
  6  5  1  0
 18 19  1  0
 13 12  1  0
 20 21  1  0
  5 10  1  0
  2  1  1  0
  7 28  1  0
  7 29  1  0
  6 26  1  0
  6 27  1  0
  5 25  1  0
 13 32  1  0
 11 30  1  0
 11 31  1  0
 15 33  1  0
 17 34  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.558   3.361  -0.607  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.500   1.947  -0.416  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.655   1.549   0.574  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.996   2.310   1.273  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.630   0.021   0.740  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.200  -0.361   2.102  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.681  -0.600   1.824  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.682  -1.091   0.399  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.609  -1.664  -0.149  0.00  0.00           O+0
HETATM   10  N   UNK     0      -2.470  -0.743  -0.170  0.00  0.00           N+0
HETATM   11  C   UNK     0      -2.128  -0.992  -1.559  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.952  -1.934  -1.694  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.193  -3.296  -1.421  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.167  -4.222  -1.510  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.431  -5.533  -1.240  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.116  -3.829  -1.867  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.067  -4.817  -1.930  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.392  -2.485  -2.139  0.00  0.00           C+0
HETATM   19 Br   UNK     0       3.184  -2.033  -2.614  0.00  0.00          Br+0
HETATM   20  C   UNK     0       0.357  -1.530  -2.050  0.00  0.00           C+0
HETATM   21 Br   UNK     0       0.722   0.317  -2.392  0.00  0.00          Br+0
HETATM   22  H   UNK     0      -2.929   3.854   0.297  0.00  0.00           H+0
HETATM   23  H   UNK     0      -1.573   3.750  -0.886  0.00  0.00           H+0
HETATM   24  H   UNK     0      -3.255   3.564  -1.424  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.591  -0.309   0.642  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.742  -1.300   2.440  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.044   0.388   2.885  0.00  0.00           H+0
HETATM   28  H   UNK     0      -4.256   0.329   1.879  0.00  0.00           H+0
HETATM   29  H   UNK     0      -4.106  -1.347   2.498  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.990  -1.443  -2.068  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.975  -0.034  -2.058  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.189  -3.634  -1.136  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.421  -5.997  -1.369  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.906  -4.395  -2.196  0.00  0.00           H+0
CONECT    1    2   22   23   24                                             
CONECT    2    3    1                                                       
CONECT    3    5    4    2                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10   25                                             
CONECT    6    7    5   26   27                                             
CONECT    7    8    6   28   29                                             
CONECT    8   10    7    9                                                  
CONECT    9    8                                                            
CONECT   10    8   11    5                                                  
CONECT   11   12   10   30   31                                             
CONECT   12   20   11   13                                                  
CONECT   13   14   12   32                                                  
CONECT   14   16   15   13                                                  
CONECT   15   14   33                                                       
CONECT   16   18   14   17                                                  
CONECT   17   16   34                                                       
CONECT   18   20   16   19                                                  
CONECT   19   18                                                            
CONECT   20   12   18   21                                                  
CONECT   21   20                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    5                                                            
CONECT   26    6                                                            
CONECT   27    6                                                            
CONECT   28    7                                                            
CONECT   29    7                                                            
CONECT   30   11                                                            
CONECT   31   11                                                            
CONECT   32   13                                                            
CONECT   33   15                                                            
CONECT   34   17                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

RDKit          3D

34 35  0  0  0  0  0  0  0  0999 V2000
   -2.5575    3.3608   -0.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4997    1.9468   -0.4158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6551    1.5485    0.5742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9956    2.3102    1.2728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6299    0.0214    0.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1995   -0.3612    2.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6807   -0.5998    1.8242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6824   -1.0913    0.3992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6087   -1.6635   -0.1491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4697   -0.7433   -0.1696 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1281   -0.9923   -1.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9517   -1.9342   -1.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1928   -3.2960   -1.4208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1665   -4.2218   -1.5100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4310   -5.5329   -1.2398 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1161   -3.8285   -1.8674 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0665   -4.8174   -1.9303 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917   -2.4852   -2.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1836   -2.0329   -2.6136 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.3571   -1.5298   -2.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7223    0.3165   -2.3922 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9291    3.8542    0.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5735    3.7502   -0.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2548    3.5637   -1.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5911   -0.3088    0.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7423   -1.3002    2.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0439    0.3877    2.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2564    0.3292    1.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1055   -1.3475    2.4982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9900   -1.4429   -2.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9754   -0.0336   -2.0582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1888   -3.6341   -1.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4205   -5.9970   -1.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9056   -4.3952   -2.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 20  2  0
 20 18  1  0
 10  8  1  0
 12 11  1  0
 11 10  1  0
  5  3  1  0
 18 16  2  0
  3  4  2  0
  8  7  1  0
  3  2  1  0
 16 14  1  0
  8  9  2  0
  7  6  1  0
 14 15  1  0
 14 13  2  0
 16 17  1  0
  6  5  1  0
 18 19  1  0
 13 12  1  0
 20 21  1  0
  5 10  1  0
  2  1  1  0
  7 28  1  0
  7 29  1  0
  6 26  1  0
  6 27  1  0
  5 25  1  0
 13 32  1  0
 11 30  1  0
 11 31  1  0
 15 33  1  0
 17 34  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
M  END

View in JSmol

Synonyms

Value	Source
Methyl (2R)-1-[(2,3-dibromo-4,5-dihydroxyphenyl)methyl]-5-oxopyrrolidine-2-carboxylic acid	Generator

Chemical Formula

C₁₃H₁₃Br₂NO₅

Average Mass

423.0570 Da

Monoisotopic Mass

420.91605 Da

IUPAC Name

methyl (2R)-1-[(2,3-dibromo-4,5-dihydroxyphenyl)methyl]-5-oxopyrrolidine-2-carboxylate

Traditional Name

methyl (2R)-1-[(2,3-dibromo-4,5-dihydroxyphenyl)methyl]-5-oxopyrrolidine-2-carboxylate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(=C(Br)C(Br)=C1O[H])C([H])([H])N1C(=O)C([H])([H])C([H])([H])[C@]1([H])C(=O)OC([H])([H])[H]

InChI Identifier

InChI=1S/C13H13Br2NO5/c1-21-13(20)7-2-3-9(18)16(7)5-6-4-8(17)12(19)11(15)10(6)14/h4,7,17,19H,2-3,5H2,1H3/t7-/m1/s1

InChI Key

ARCCBVHXHHINEZ-SSDOTTSWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Rhodomela confervoides	JEOL database	Zhao, J., et al, J. Nat. Prod. 68, 691 (2005)

Chemical Taxonomy

Classification

Not classified

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	2.74	ALOGPS
logP	2.13	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	7.54	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	87.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	81.57 m³·mol⁻¹	ChemAxon
Polarizability	32.38 Å³	ChemAxon
Number of Rings	2	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

13082501

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15939552

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhao, J., et al. (2005). Zhao, J., et al, J. Nat. Prod. 68, 691 (2005). J. Nat. Prod..

Showing NP-Card for N-(2,3-dibromo-4,5-dihydroxybenzyl)methyl pyroglutamate (NP0028121)

MOL for NP0028121 (N-(2,3-dibromo-4,5-dihydroxybenzyl)methyl pyroglutamate)

3D MOL for NP0028121 (N-(2,3-dibromo-4,5-dihydroxybenzyl)methyl pyroglutamate)

3D SDF for NP0028121 (N-(2,3-dibromo-4,5-dihydroxybenzyl)methyl pyroglutamate)

3D-SDF for NP0028121 (N-(2,3-dibromo-4,5-dihydroxybenzyl)methyl pyroglutamate)

PDB for NP0028121 (N-(2,3-dibromo-4,5-dihydroxybenzyl)methyl pyroglutamate)

3D PDB for NP0028121 (N-(2,3-dibromo-4,5-dihydroxybenzyl)methyl pyroglutamate)

SMILES for NP0028121 (N-(2,3-dibromo-4,5-dihydroxybenzyl)methyl pyroglutamate)

INCHI for NP0028121 (N-(2,3-dibromo-4,5-dihydroxybenzyl)methyl pyroglutamate)

Structure for NP0028121 (N-(2,3-dibromo-4,5-dihydroxybenzyl)methyl pyroglutamate)

3D Structure for NP0028121 (N-(2,3-dibromo-4,5-dihydroxybenzyl)methyl pyroglutamate)