NP-MRD: Showing NP-Card for methyl 5,5,5-trichloro-4-methyl-2-[methyl(4,4,4-trichloro-3-methyl-1-oxob+ (NP0025376)

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Record Information

Version

2.0

Created at

2021-06-19 17:30:50 UTC

Updated at

2021-06-29 23:50:17 UTC

NP-MRD ID

NP0025376

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 5,5,5-trichloro-4-methyl-2-[methyl(4,4,4-trichloro-3-methyl-1-oxob+

Provided By

JEOL Database JEOL Logo

Description

(2S,4S)-2-[[(3S)-3-Methyl-4,4,4-trichlorobutyryl](methyl)amino]-4-methyl-5,5,5-trichlorovaleric acid methyl ester belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids. methyl 5,5,5-trichloro-4-methyl-2-[methyl(4,4,4-trichloro-3-methyl-1-oxob+ is found in Dysidea sp. methyl 5,5,5-trichloro-4-methyl-2-[methyl(4,4,4-trichloro-3-methyl-1-oxob+ was first documented in 2001 (Stapleton, B. L., et al.). Based on a literature review very few articles have been published on (2S,4S)-2-[[(3S)-3-Methyl-4,4,4-trichlorobutyryl](methyl)amino]-4-methyl-5,5,5-trichlorovaleric acid methyl ester.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119303D          

 42 41  0  0  0  0            999 V2000
    2.0007    3.0482   -4.5840 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4088    2.6151   -3.3587 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7767    1.4096   -3.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6877    0.7445   -4.4644 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2027    0.9548   -2.0764 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2338    0.4143   -2.2527 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8329   -0.2566   -0.9795 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0669   -1.5587   -0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3742   -0.4756   -1.0813 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8204   -1.5491   -2.4433 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2272    1.0991   -1.3051 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.0350   -1.1854    0.4362 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.3037    1.9873   -1.0133 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6184    3.1208   -1.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3421    1.8764   -0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1699    0.9680   -0.1545 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4122    2.9286    1.0059 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3970    2.5543    2.1445 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7525    1.4550    3.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8545    3.7894    2.9679 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9804    3.3229    4.2912 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7470    4.9610    1.9278 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4648    4.6591    3.7026 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4872    4.0106   -4.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7598    2.3337   -4.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2330    3.1870   -5.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8520    0.1156   -1.8051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8698    1.2362   -2.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2387   -0.3159   -3.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6634    0.4139   -0.1265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4607   -2.0705    0.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0137   -1.3550   -0.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1052   -2.2572   -1.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5330    2.8476   -0.5335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1946    4.0131   -0.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8597    3.3633   -2.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4083    3.0784    1.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7219    3.8560    0.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2992    2.1137    1.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8605    1.8185    3.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4502    1.0707    3.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4478    0.5981    2.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 11  1  6  0  0  0
 10  9  1  0  0  0  0
  9 12  1  0  0  0  0
 13 15  1  0  0  0  0
 20 22  1  6  0  0  0
  7  6  1  0  0  0  0
 20 23  1  0  0  0  0
 15 17  1  0  0  0  0
 18 19  1  0  0  0  0
 15 16  2  0  0  0  0
 17 18  1  0  0  0  0
 13 14  1  0  0  0  0
  6  5  1  0  0  0  0
  7  8  1  0  0  0  0
 18 20  1  0  0  0  0
  5  3  1  0  0  0  0
  9  7  1  0  0  0  0
  3  4  2  0  0  0  0
 20 21  1  0  0  0  0
  3  2  1  0  0  0  0
  5 13  1  0  0  0  0
  2  1  1  0  0  0  0
  7 30  1  1  0  0  0
  6 28  1  0  0  0  0
  6 29  1  0  0  0  0
  5 27  1  1  0  0  0
 17 37  1  0  0  0  0
 17 38  1  0  0  0  0
 18 39  1  6  0  0  0
 19 40  1  0  0  0  0
 19 41  1  0  0  0  0
 19 42  1  0  0  0  0
 14 34  1  0  0  0  0
 14 35  1  0  0  0  0
 14 36  1  0  0  0  0
  8 31  1  0  0  0  0
  8 32  1  0  0  0  0
  8 33  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
M  END

     RDKit          3D

 42 41  0  0  0  0  0  0  0  0999 V2000
    2.0007    3.0482   -4.5840 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4088    2.6151   -3.3587 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7767    1.4096   -3.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6877    0.7445   -4.4644 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2027    0.9548   -2.0764 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2338    0.4143   -2.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8329   -0.2566   -0.9795 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0669   -1.5587   -0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3742   -0.4756   -1.0813 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8204   -1.5491   -2.4433 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2272    1.0991   -1.3051 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.0350   -1.1854    0.4362 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.3037    1.9873   -1.0133 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6184    3.1208   -1.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3421    1.8764   -0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1699    0.9680   -0.1545 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4122    2.9286    1.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3970    2.5543    2.1445 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7525    1.4550    3.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8545    3.7894    2.9679 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9804    3.3229    4.2912 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7470    4.9610    1.9278 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4648    4.6591    3.7026 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4872    4.0106   -4.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7598    2.3337   -4.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2330    3.1870   -5.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8520    0.1156   -1.8051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8698    1.2362   -2.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2387   -0.3159   -3.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6634    0.4139   -0.1265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4607   -2.0705    0.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0137   -1.3550   -0.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1052   -2.2572   -1.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5330    2.8476   -0.5335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1946    4.0131   -0.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8597    3.3633   -2.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4083    3.0784    1.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7219    3.8560    0.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2992    2.1137    1.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8605    1.8185    3.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4502    1.0707    3.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4478    0.5981    2.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 11  1  6
 10  9  1  0
  9 12  1  0
 13 15  1  0
 20 22  1  6
  7  6  1  0
 20 23  1  0
 15 17  1  0
 18 19  1  0
 15 16  2  0
 17 18  1  0
 13 14  1  0
  6  5  1  0
  7  8  1  0
 18 20  1  0
  5  3  1  0
  9  7  1  0
  3  4  2  0
 20 21  1  0
  3  2  1  0
  5 13  1  0
  2  1  1  0
  7 30  1  1
  6 28  1  0
  6 29  1  0
  5 27  1  1
 17 37  1  0
 17 38  1  0
 18 39  1  6
 19 40  1  0
 19 41  1  0
 19 42  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
M  END


  Mrv1652306192119303D          

 42 41  0  0  0  0            999 V2000
    2.0007    3.0482   -4.5840 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4088    2.6151   -3.3587 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7767    1.4096   -3.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6877    0.7445   -4.4644 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2027    0.9548   -2.0764 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2338    0.4143   -2.2527 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8329   -0.2566   -0.9795 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0669   -1.5587   -0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3742   -0.4756   -1.0813 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8204   -1.5491   -2.4433 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2272    1.0991   -1.3051 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.0350   -1.1854    0.4362 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.3037    1.9873   -1.0133 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6184    3.1208   -1.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3421    1.8764   -0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1699    0.9680   -0.1545 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4122    2.9286    1.0059 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3970    2.5543    2.1445 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7525    1.4550    3.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8545    3.7894    2.9679 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9804    3.3229    4.2912 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7470    4.9610    1.9278 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4648    4.6591    3.7026 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4872    4.0106   -4.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7598    2.3337   -4.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2330    3.1870   -5.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8520    0.1156   -1.8051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8698    1.2362   -2.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2387   -0.3159   -3.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6634    0.4139   -0.1265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4607   -2.0705    0.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0137   -1.3550   -0.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1052   -2.2572   -1.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5330    2.8476   -0.5335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1946    4.0131   -0.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8597    3.3633   -2.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4083    3.0784    1.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7219    3.8560    0.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2992    2.1137    1.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8605    1.8185    3.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4502    1.0707    3.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4478    0.5981    2.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 11  1  6  0  0  0
 10  9  1  0  0  0  0
  9 12  1  0  0  0  0
 13 15  1  0  0  0  0
 20 22  1  6  0  0  0
  7  6  1  0  0  0  0
 20 23  1  0  0  0  0
 15 17  1  0  0  0  0
 18 19  1  0  0  0  0
 15 16  2  0  0  0  0
 17 18  1  0  0  0  0
 13 14  1  0  0  0  0
  6  5  1  0  0  0  0
  7  8  1  0  0  0  0
 18 20  1  0  0  0  0
  5  3  1  0  0  0  0
  9  7  1  0  0  0  0
  3  4  2  0  0  0  0
 20 21  1  0  0  0  0
  3  2  1  0  0  0  0
  5 13  1  0  0  0  0
  2  1  1  0  0  0  0
  7 30  1  1  0  0  0
  6 28  1  0  0  0  0
  6 29  1  0  0  0  0
  5 27  1  1  0  0  0
 17 37  1  0  0  0  0
 17 38  1  0  0  0  0
 18 39  1  6  0  0  0
 19 40  1  0  0  0  0
 19 41  1  0  0  0  0
 19 42  1  0  0  0  0
 14 34  1  0  0  0  0
 14 35  1  0  0  0  0
 14 36  1  0  0  0  0
  8 31  1  0  0  0  0
  8 32  1  0  0  0  0
  8 33  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025376

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])([H])OC(=O)[C@@]([H])(N(C(=O)C([H])([H])[C@]([H])(C([H])([H])[H])C(Cl)(Cl)Cl)C([H])([H])[H])C([H])([H])[C@]([H])(C([H])([H])[H])C(Cl)(Cl)Cl

> <INCHI_IDENTIFIER>
InChI=1S/C13H19Cl6NO3/c1-7(12(14,15)16)5-9(11(22)23-4)20(3)10(21)6-8(2)13(17,18)19/h7-9H,5-6H2,1-4H3/t7-,8-,9-/m0/s1

> <INCHI_KEY>
LZMPHAKNNSOSQK-CIUDSAMLSA-N

> <FORMULA>
C13H19Cl6NO3

> <MOLECULAR_WEIGHT>
450.0

> <EXACT_MASS>
446.9496097

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
40.17450547693611

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2S,4S)-5,5,5-trichloro-4-methyl-2-[(3S)-4,4,4-trichloro-N,3-dimethylbutanamido]pentanoate

> <ALOGPS_LOGP>
4.52

> <JCHEM_LOGP>
4.090647389333334

> <ALOGPS_LOGS>
-6.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3771603544972724

> <JCHEM_POLAR_SURFACE_AREA>
46.61

> <JCHEM_REFRACTIVITY>
97.78159999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.11e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2S,4S)-5,5,5-trichloro-4-methyl-2-[(3S)-4,4,4-trichloro-N,3-dimethylbutanamido]pentanoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 42 41  0  0  0  0  0  0  0  0999 V2000
    2.0007    3.0482   -4.5840 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4088    2.6151   -3.3587 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7767    1.4096   -3.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6877    0.7445   -4.4644 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2027    0.9548   -2.0764 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2338    0.4143   -2.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8329   -0.2566   -0.9795 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0669   -1.5587   -0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3742   -0.4756   -1.0813 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8204   -1.5491   -2.4433 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2272    1.0991   -1.3051 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.0350   -1.1854    0.4362 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.3037    1.9873   -1.0133 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6184    3.1208   -1.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3421    1.8764   -0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1699    0.9680   -0.1545 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4122    2.9286    1.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3970    2.5543    2.1445 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7525    1.4550    3.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8545    3.7894    2.9679 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9804    3.3229    4.2912 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7470    4.9610    1.9278 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4648    4.6591    3.7026 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4872    4.0106   -4.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7598    2.3337   -4.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2330    3.1870   -5.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8520    0.1156   -1.8051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8698    1.2362   -2.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2387   -0.3159   -3.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6634    0.4139   -0.1265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4607   -2.0705    0.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0137   -1.3550   -0.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1052   -2.2572   -1.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5330    2.8476   -0.5335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1946    4.0131   -0.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8597    3.3633   -2.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4083    3.0784    1.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7219    3.8560    0.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2992    2.1137    1.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8605    1.8185    3.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4502    1.0707    3.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4478    0.5981    2.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 11  1  6
 10  9  1  0
  9 12  1  0
 13 15  1  0
 20 22  1  6
  7  6  1  0
 20 23  1  0
 15 17  1  0
 18 19  1  0
 15 16  2  0
 17 18  1  0
 13 14  1  0
  6  5  1  0
  7  8  1  0
 18 20  1  0
  5  3  1  0
  9  7  1  0
  3  4  2  0
 20 21  1  0
  3  2  1  0
  5 13  1  0
  2  1  1  0
  7 30  1  1
  6 28  1  0
  6 29  1  0
  5 27  1  1
 17 37  1  0
 17 38  1  0
 18 39  1  6
 19 40  1  0
 19 41  1  0
 19 42  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  1 24  1  0
  1 25  1  0
  1 26  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       2.001   3.048  -4.584  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.409   2.615  -3.359  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.777   1.410  -3.438  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.688   0.745  -4.464  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.203   0.955  -2.076  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.234   0.414  -2.253  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.833  -0.257  -0.980  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.067  -1.559  -0.673  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.374  -0.476  -1.081  0.00  0.00           C+0
HETATM   10 Cl   UNK     0      -3.820  -1.549  -2.443  0.00  0.00          Cl+0
HETATM   11 Cl   UNK     0      -4.227   1.099  -1.305  0.00  0.00          Cl+0
HETATM   12 Cl   UNK     0      -4.035  -1.185   0.436  0.00  0.00          Cl+0
HETATM   13  N   UNK     0       0.304   1.987  -1.013  0.00  0.00           N+0
HETATM   14  C   UNK     0      -0.618   3.121  -1.066  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.342   1.876  -0.094  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.170   0.968  -0.155  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.412   2.929   1.006  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.397   2.554   2.144  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.753   1.455   3.014  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.854   3.789   2.968  0.00  0.00           C+0
HETATM   21 Cl   UNK     0       3.980   3.323   4.291  0.00  0.00          Cl+0
HETATM   22 Cl   UNK     0       3.747   4.961   1.928  0.00  0.00          Cl+0
HETATM   23 Cl   UNK     0       1.465   4.659   3.703  0.00  0.00          Cl+0
HETATM   24  H   UNK     0       2.487   4.011  -4.403  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.760   2.334  -4.918  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.233   3.187  -5.352  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.852   0.116  -1.805  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.870   1.236  -2.597  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.239  -0.316  -3.072  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.663   0.414  -0.127  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.461  -2.071   0.209  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.014  -1.355  -0.458  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.105  -2.257  -1.515  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.533   2.848  -0.534  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.195   4.013  -0.602  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.860   3.363  -2.104  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.408   3.078   1.420  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.722   3.856   0.515  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.299   2.114   1.698  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.861   1.819   3.534  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.450   1.071   3.763  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.448   0.598   2.404  0.00  0.00           H+0
CONECT    1    2   24   25   26                                             
CONECT    2    3    1                                                       
CONECT    3    5    4    2                                                  
CONECT    4    3                                                            
CONECT    5    6    3   13   27                                             
CONECT    6    7    5   28   29                                             
CONECT    7    6    8    9   30                                             
CONECT    8    7   31   32   33                                             
CONECT    9   11   10   12    7                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9                                                            
CONECT   13   15   14    5                                                  
CONECT   14   13   34   35   36                                             
CONECT   15   13   17   16                                                  
CONECT   16   15                                                            
CONECT   17   15   18   37   38                                             
CONECT   18   19   17   20   39                                             
CONECT   19   18   40   41   42                                             
CONECT   20   22   23   18   21                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    5                                                            
CONECT   28    6                                                            
CONECT   29    6                                                            
CONECT   30    7                                                            
CONECT   31    8                                                            
CONECT   32    8                                                            
CONECT   33    8                                                            
CONECT   34   14                                                            
CONECT   35   14                                                            
CONECT   36   14                                                            
CONECT   37   17                                                            
CONECT   38   17                                                            
CONECT   39   18                                                            
CONECT   40   19                                                            
CONECT   41   19                                                            
CONECT   42   19                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   82    0
END

RDKit          3D

42 41  0  0  0  0  0  0  0  0999 V2000
    2.0007    3.0482   -4.5840 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4088    2.6151   -3.3587 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7767    1.4096   -3.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6877    0.7445   -4.4644 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2027    0.9548   -2.0764 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2338    0.4143   -2.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8329   -0.2566   -0.9795 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0669   -1.5587   -0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3742   -0.4756   -1.0813 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8204   -1.5491   -2.4433 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2272    1.0991   -1.3051 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.0350   -1.1854    0.4362 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.3037    1.9873   -1.0133 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6184    3.1208   -1.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3421    1.8764   -0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1699    0.9680   -0.1545 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4122    2.9286    1.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3970    2.5543    2.1445 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7525    1.4550    3.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8545    3.7894    2.9679 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9804    3.3229    4.2912 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7470    4.9610    1.9278 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4648    4.6591    3.7026 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4872    4.0106   -4.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7598    2.3337   -4.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2330    3.1870   -5.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8520    0.1156   -1.8051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8698    1.2362   -2.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2387   -0.3159   -3.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6634    0.4139   -0.1265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4607   -2.0705    0.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0137   -1.3550   -0.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1052   -2.2572   -1.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5330    2.8476   -0.5335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1946    4.0131   -0.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8597    3.3633   -2.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4083    3.0784    1.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7219    3.8560    0.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2992    2.1137    1.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8605    1.8185    3.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4502    1.0707    3.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4478    0.5981    2.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 11  1  6
 10  9  1  0
  9 12  1  0
 13 15  1  0
 20 22  1  6
  7  6  1  0
 20 23  1  0
 15 17  1  0
 18 19  1  0
 15 16  2  0
 17 18  1  0
 13 14  1  0
  6  5  1  0
  7  8  1  0
 18 20  1  0
  5  3  1  0
  9  7  1  0
  3  4  2  0
 20 21  1  0
  3  2  1  0
  5 13  1  0
  2  1  1  0
  7 30  1  1
  6 28  1  0
  6 29  1  0
  5 27  1  1
 17 37  1  0
 17 38  1  0
 18 39  1  6
 19 40  1  0
 19 41  1  0
 19 42  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
M  END

View in JSmol

Synonyms

Value	Source
(2S,4S)-2-[[(3S)-3-Methyl-4,4,4-trichlorobutyryl](methyl)amino]-4-methyl-5,5,5-trichlorovalerate methyl ester	Generator

Chemical Formula

C₁₃H₁₉Cl₆NO₃

Average Mass

450.0000 Da

Monoisotopic Mass

446.94961 Da

IUPAC Name

methyl (2S,4S)-5,5,5-trichloro-4-methyl-2-[(3S)-4,4,4-trichloro-N,3-dimethylbutanamido]pentanoate

Traditional Name

methyl (2S,4S)-5,5,5-trichloro-4-methyl-2-[(3S)-4,4,4-trichloro-N,3-dimethylbutanamido]pentanoate

CAS Registry Number

Not Available

SMILES

[H]C([H])([H])OC(=O)[C@@]([H])(N(C(=O)C([H])([H])[C@]([H])(C([H])([H])[H])C(Cl)(Cl)Cl)C([H])([H])[H])C([H])([H])[C@]([H])(C([H])([H])[H])C(Cl)(Cl)Cl

InChI Identifier

InChI=1S/C13H19Cl6NO3/c1-7(12(14,15)16)5-9(11(22)23-4)20(3)10(21)6-8(2)13(17,18)19/h7-9H,5-6H2,1-4H3/t7-,8-,9-/m0/s1

InChI Key

LZMPHAKNNSOSQK-CIUDSAMLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, 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
Dysidea sp.	JEOL database	Stapleton, B. L., et al, Tetrahedron 57, 4603 (2001)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.

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 acid esters

Alternative Parents

Substituents

Alpha-amino acid ester
Fatty acid ester
N-acyl-amine
Fatty acyl
Tertiary carboxylic acid amide
Methyl ester
Carboxamide group
Carboxylic acid ester
Monocarboxylic acid or derivatives
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organopnictogen compound
Organic oxygen compound
Alkyl chloride
Carbonyl group
Organic nitrogen compound
Alkyl halide
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	4.52	ALOGPS
logP	4.09	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	46.61 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	97.78 m³·mol⁻¹	ChemAxon
Polarizability	40.17 Å³	ChemAxon
Number of Rings	0	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

10273536

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21637953

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Stapleton, B. L., et al. (2001). Stapleton, B. L., et al, Tetrahedron 57, 4603 (2001). Tetrahedron.

Showing NP-Card for methyl 5,5,5-trichloro-4-methyl-2-[methyl(4,4,4-trichloro-3-methyl-1-oxob+ (NP0025376)

MOL for NP0025376 (methyl 5,5,5-trichloro-4-methyl-2-[methyl(4,4,4-trichloro-3-methyl-1-oxob+)

3D MOL for NP0025376 (methyl 5,5,5-trichloro-4-methyl-2-[methyl(4,4,4-trichloro-3-methyl-1-oxob+)

3D SDF for NP0025376 (methyl 5,5,5-trichloro-4-methyl-2-[methyl(4,4,4-trichloro-3-methyl-1-oxob+)

3D-SDF for NP0025376 (methyl 5,5,5-trichloro-4-methyl-2-[methyl(4,4,4-trichloro-3-methyl-1-oxob+)

PDB for NP0025376 (methyl 5,5,5-trichloro-4-methyl-2-[methyl(4,4,4-trichloro-3-methyl-1-oxob+)

3D PDB for NP0025376 (methyl 5,5,5-trichloro-4-methyl-2-[methyl(4,4,4-trichloro-3-methyl-1-oxob+)

SMILES for NP0025376 (methyl 5,5,5-trichloro-4-methyl-2-[methyl(4,4,4-trichloro-3-methyl-1-oxob+)

INCHI for NP0025376 (methyl 5,5,5-trichloro-4-methyl-2-[methyl(4,4,4-trichloro-3-methyl-1-oxob+)

Structure for NP0025376 (methyl 5,5,5-trichloro-4-methyl-2-[methyl(4,4,4-trichloro-3-methyl-1-oxob+)

3D Structure for NP0025376 (methyl 5,5,5-trichloro-4-methyl-2-[methyl(4,4,4-trichloro-3-methyl-1-oxob+)