NP-MRD: Showing NP-Card for herbacic acid (NP0039200)

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Record Information

Version

2.0

Created at

2021-06-20 21:41:43 UTC

Updated at

2021-06-30 00:12:24 UTC

NP-MRD ID

NP0039200

Secondary Accession Numbers

None

Natural Product Identification

Common Name

herbacic acid

Provided By

JEOL Database JEOL Logo

Description

Herbacic acid, also known as herbacate, belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom. herbacic acid is found in Dysidea herbacea and Lamellodysidea herbacea. herbacic acid was first documented in 2000 (PMID: 10650102). Based on a literature review very few articles have been published on Herbacic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123413D          

 43 42  0  0  0  0            999 V2000
    3.7333    1.1124    3.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5819    2.0067    2.4499 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8211    1.1758    1.1619 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8280    0.0889    0.8726 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9905    0.1057   -0.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0580   -1.0260   -0.4026 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2894   -2.1431    0.0564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0871   -0.7828   -1.1327 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6420    0.5532   -1.3359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8608   -1.9022   -1.7304 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0099   -2.8226   -2.6381 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7297   -2.0939   -3.7985 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3021   -1.6044   -4.8339 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8601   -2.9619   -4.4355 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1214   -3.3682   -3.2157 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2330   -4.4879   -5.1312 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7101   -2.0579   -5.7436 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6683   -2.7744   -0.7471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7118   -3.3292   -1.0747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1100   -2.9918    0.4603 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2866    2.8705    2.4664 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3328    4.0359    3.8456 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1387    3.8623    0.9683 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7785    1.9127    2.6364 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.6867    0.5730    3.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7318    1.7015    4.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9357    0.3674    3.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4275    2.7109    2.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9077    1.8472    0.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8075    0.6978    1.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173   -0.7620    1.5541 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9937    0.9186   -0.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1969    1.2936   -0.6681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7174    0.5266   -1.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4705    0.8463   -2.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6315   -1.4322   -2.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7012   -3.3693   -2.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6661   -3.5959   -3.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2144   -1.1977   -3.3890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1687   -1.0645   -5.6600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0133   -0.9060   -4.3832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8764   -2.4354   -5.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1703   -2.6938    0.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0  0  0  0
  2 21  1  0  0  0  0
  8  9  1  0  0  0  0
  2  1  1  0  0  0  0
 10 11  1  0  0  0  0
 21 22  1  1  0  0  0
  8  6  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
  6  5  1  0  0  0  0
 12 14  1  0  0  0  0
 10 18  1  0  0  0  0
 14 15  1  1  0  0  0
  5  4  2  0  0  0  0
 14 16  1  0  0  0  0
 12 11  1  0  0  0  0
 14 17  1  0  0  0  0
  4  3  1  0  0  0  0
  6  7  2  0  0  0  0
 10  8  1  0  0  0  0
 18 19  2  0  0  0  0
  3  2  1  0  0  0  0
 18 20  1  0  0  0  0
 13 40  1  0  0  0  0
 13 41  1  0  0  0  0
 13 42  1  0  0  0  0
 12 39  1  1  0  0  0
 11 37  1  0  0  0  0
 11 38  1  0  0  0  0
 10 36  1  6  0  0  0
  9 33  1  0  0  0  0
  9 34  1  0  0  0  0
  9 35  1  0  0  0  0
  5 32  1  0  0  0  0
  4 31  1  0  0  0  0
  3 29  1  0  0  0  0
  3 30  1  0  0  0  0
  2 28  1  1  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
 20 43  1  0  0  0  0
M  END

     RDKit          3D

 43 42  0  0  0  0  0  0  0  0999 V2000
    3.7333    1.1124    3.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5819    2.0067    2.4499 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8211    1.1758    1.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8280    0.0889    0.8726 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9905    0.1057   -0.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0580   -1.0260   -0.4026 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2894   -2.1431    0.0564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0871   -0.7828   -1.1327 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6420    0.5532   -1.3359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8608   -1.9022   -1.7304 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0099   -2.8226   -2.6381 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7297   -2.0939   -3.7985 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3021   -1.6044   -4.8339 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8601   -2.9619   -4.4355 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1214   -3.3682   -3.2157 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2330   -4.4879   -5.1312 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7101   -2.0579   -5.7436 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6683   -2.7744   -0.7471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7118   -3.3292   -1.0747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1100   -2.9918    0.4603 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2866    2.8705    2.4664 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3328    4.0359    3.8456 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1387    3.8623    0.9683 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7785    1.9127    2.6364 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.6867    0.5730    3.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7318    1.7015    4.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9357    0.3674    3.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4275    2.7109    2.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9077    1.8472    0.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8075    0.6978    1.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173   -0.7620    1.5541 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9937    0.9186   -0.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1969    1.2936   -0.6681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7174    0.5266   -1.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4705    0.8463   -2.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6315   -1.4322   -2.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7012   -3.3693   -2.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6661   -3.5959   -3.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2144   -1.1977   -3.3890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1687   -1.0645   -5.6600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0133   -0.9060   -4.3832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8764   -2.4354   -5.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1703   -2.6938    0.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
  2 21  1  0
  8  9  1  0
  2  1  1  0
 10 11  1  0
 21 22  1  1
  8  6  1  0
 21 23  1  0
 21 24  1  0
  6  5  1  0
 12 14  1  0
 10 18  1  0
 14 15  1  1
  5  4  2  0
 14 16  1  0
 12 11  1  0
 14 17  1  0
  4  3  1  0
  6  7  2  0
 10  8  1  0
 18 19  2  0
  3  2  1  0
 18 20  1  0
 13 40  1  0
 13 41  1  0
 13 42  1  0
 12 39  1  1
 11 37  1  0
 11 38  1  0
 10 36  1  6
  9 33  1  0
  9 34  1  0
  9 35  1  0
  5 32  1  0
  4 31  1  0
  3 29  1  0
  3 30  1  0
  2 28  1  1
  1 25  1  0
  1 26  1  0
  1 27  1  0
 20 43  1  0
M  END


  Mrv1652306202123413D          

 43 42  0  0  0  0            999 V2000
    3.7333    1.1124    3.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5819    2.0067    2.4499 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8211    1.1758    1.1619 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8280    0.0889    0.8726 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9905    0.1057   -0.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0580   -1.0260   -0.4026 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2894   -2.1431    0.0564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0871   -0.7828   -1.1327 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6420    0.5532   -1.3359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8608   -1.9022   -1.7304 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0099   -2.8226   -2.6381 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7297   -2.0939   -3.7985 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3021   -1.6044   -4.8339 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8601   -2.9619   -4.4355 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1214   -3.3682   -3.2157 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2330   -4.4879   -5.1312 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7101   -2.0579   -5.7436 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6683   -2.7744   -0.7471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7118   -3.3292   -1.0747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1100   -2.9918    0.4603 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2866    2.8705    2.4664 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3328    4.0359    3.8456 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1387    3.8623    0.9683 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7785    1.9127    2.6364 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.6867    0.5730    3.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7318    1.7015    4.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9357    0.3674    3.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4275    2.7109    2.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9077    1.8472    0.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8075    0.6978    1.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173   -0.7620    1.5541 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9937    0.9186   -0.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1969    1.2936   -0.6681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7174    0.5266   -1.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4705    0.8463   -2.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6315   -1.4322   -2.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7012   -3.3693   -2.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6661   -3.5959   -3.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2144   -1.1977   -3.3890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1687   -1.0645   -5.6600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0133   -0.9060   -4.3832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8764   -2.4354   -5.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1703   -2.6938    0.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0  0  0  0
  2 21  1  0  0  0  0
  8  9  1  0  0  0  0
  2  1  1  0  0  0  0
 10 11  1  0  0  0  0
 21 22  1  1  0  0  0
  8  6  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
  6  5  1  0  0  0  0
 12 14  1  0  0  0  0
 10 18  1  0  0  0  0
 14 15  1  1  0  0  0
  5  4  2  0  0  0  0
 14 16  1  0  0  0  0
 12 11  1  0  0  0  0
 14 17  1  0  0  0  0
  4  3  1  0  0  0  0
  6  7  2  0  0  0  0
 10  8  1  0  0  0  0
 18 19  2  0  0  0  0
  3  2  1  0  0  0  0
 18 20  1  0  0  0  0
 13 40  1  0  0  0  0
 13 41  1  0  0  0  0
 13 42  1  0  0  0  0
 12 39  1  1  0  0  0
 11 37  1  0  0  0  0
 11 38  1  0  0  0  0
 10 36  1  6  0  0  0
  9 33  1  0  0  0  0
  9 34  1  0  0  0  0
  9 35  1  0  0  0  0
  5 32  1  0  0  0  0
  4 31  1  0  0  0  0
  3 29  1  0  0  0  0
  3 30  1  0  0  0  0
  2 28  1  1  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
 20 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0039200

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@@]([H])(N(C(=O)C(\[H])=C(/[H])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/C14H19Cl6NO3/c1-8(13(15,16)17)5-4-6-11(22)21(3)10(12(23)24)7-9(2)14(18,19)20/h4,6,8-10H,5,7H2,1-3H3,(H,23,24)/b6-4+/t8-,9-,10-/m0/s1

> <INCHI_KEY>
FYSJFLMSVGZPJE-ZNSGJFPESA-N

> <FORMULA>
C14H19Cl6NO3

> <MOLECULAR_WEIGHT>
462.01

> <EXACT_MASS>
458.9496097

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
40.94635866584227

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,4S)-5,5,5-trichloro-4-methyl-2-[(2E,5S)-6,6,6-trichloro-N,5-dimethylhex-2-enamido]pentanoic acid

> <ALOGPS_LOGP>
4.65

> <JCHEM_LOGP>
4.831714153

> <ALOGPS_LOGS>
-6.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.322620976650957

> <JCHEM_PKA_STRONGEST_BASIC>
-0.33188169053017835

> <JCHEM_POLAR_SURFACE_AREA>
57.61

> <JCHEM_REFRACTIVITY>
103.30779999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.08e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4S)-5,5,5-trichloro-4-methyl-2-[(2E,5S)-6,6,6-trichloro-N,5-dimethylhex-2-enamido]pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 43 42  0  0  0  0  0  0  0  0999 V2000
    3.7333    1.1124    3.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5819    2.0067    2.4499 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8211    1.1758    1.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8280    0.0889    0.8726 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9905    0.1057   -0.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0580   -1.0260   -0.4026 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2894   -2.1431    0.0564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0871   -0.7828   -1.1327 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6420    0.5532   -1.3359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8608   -1.9022   -1.7304 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0099   -2.8226   -2.6381 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7297   -2.0939   -3.7985 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3021   -1.6044   -4.8339 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8601   -2.9619   -4.4355 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1214   -3.3682   -3.2157 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2330   -4.4879   -5.1312 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7101   -2.0579   -5.7436 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6683   -2.7744   -0.7471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7118   -3.3292   -1.0747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1100   -2.9918    0.4603 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2866    2.8705    2.4664 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3328    4.0359    3.8456 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1387    3.8623    0.9683 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7785    1.9127    2.6364 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.6867    0.5730    3.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7318    1.7015    4.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9357    0.3674    3.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4275    2.7109    2.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9077    1.8472    0.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8075    0.6978    1.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173   -0.7620    1.5541 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9937    0.9186   -0.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1969    1.2936   -0.6681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7174    0.5266   -1.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4705    0.8463   -2.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6315   -1.4322   -2.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7012   -3.3693   -2.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6661   -3.5959   -3.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2144   -1.1977   -3.3890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1687   -1.0645   -5.6600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0133   -0.9060   -4.3832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8764   -2.4354   -5.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1703   -2.6938    0.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
  2 21  1  0
  8  9  1  0
  2  1  1  0
 10 11  1  0
 21 22  1  1
  8  6  1  0
 21 23  1  0
 21 24  1  0
  6  5  1  0
 12 14  1  0
 10 18  1  0
 14 15  1  1
  5  4  2  0
 14 16  1  0
 12 11  1  0
 14 17  1  0
  4  3  1  0
  6  7  2  0
 10  8  1  0
 18 19  2  0
  3  2  1  0
 18 20  1  0
 13 40  1  0
 13 41  1  0
 13 42  1  0
 12 39  1  1
 11 37  1  0
 11 38  1  0
 10 36  1  6
  9 33  1  0
  9 34  1  0
  9 35  1  0
  5 32  1  0
  4 31  1  0
  3 29  1  0
  3 30  1  0
  2 28  1  1
  1 25  1  0
  1 26  1  0
  1 27  1  0
 20 43  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       3.733   1.112   3.695  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.582   2.007   2.450  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.821   1.176   1.162  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.828   0.089   0.873  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.990   0.106  -0.177  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.058  -1.026  -0.403  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.289  -2.143   0.056  0.00  0.00           O+0
HETATM    8  N   UNK     0      -0.087  -0.783  -1.133  0.00  0.00           N+0
HETATM    9  C   UNK     0      -0.642   0.553  -1.336  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.861  -1.902  -1.730  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.010  -2.823  -2.638  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.730  -2.094  -3.799  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.302  -1.604  -4.834  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.860  -2.962  -4.436  0.00  0.00           C+0
HETATM   15 Cl   UNK     0       3.121  -3.368  -3.216  0.00  0.00          Cl+0
HETATM   16 Cl   UNK     0       1.233  -4.488  -5.131  0.00  0.00          Cl+0
HETATM   17 Cl   UNK     0       2.710  -2.058  -5.744  0.00  0.00          Cl+0
HETATM   18  C   UNK     0      -1.668  -2.774  -0.747  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.712  -3.329  -1.075  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.110  -2.992   0.460  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.287   2.870   2.466  0.00  0.00           C+0
HETATM   22 Cl   UNK     0       2.333   4.036   3.846  0.00  0.00          Cl+0
HETATM   23 Cl   UNK     0       2.139   3.862   0.968  0.00  0.00          Cl+0
HETATM   24 Cl   UNK     0       0.779   1.913   2.636  0.00  0.00          Cl+0
HETATM   25  H   UNK     0       4.687   0.573   3.664  0.00  0.00           H+0
HETATM   26  H   UNK     0       3.732   1.702   4.617  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.936   0.367   3.771  0.00  0.00           H+0
HETATM   28  H   UNK     0       4.428   2.711   2.487  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.908   1.847   0.299  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.808   0.698   1.238  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.817  -0.762   1.554  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.994   0.919  -0.892  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.197   1.294  -0.668  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.717   0.527  -1.134  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.471   0.846  -2.375  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.632  -1.432  -2.355  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.701  -3.369  -2.012  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.666  -3.596  -3.060  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.214  -1.198  -3.389  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.169  -1.065  -5.660  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.013  -0.906  -4.383  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.876  -2.435  -5.256  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.170  -2.694   0.507  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2   21    1    3   28                                             
CONECT    3    4    2   29   30                                             
CONECT    4    5    3   31                                                  
CONECT    5    6    4   32                                                  
CONECT    6    8    5    7                                                  
CONECT    7    6                                                            
CONECT    8    9    6   10                                                  
CONECT    9    8   33   34   35                                             
CONECT   10   11   18    8   36                                             
CONECT   11   10   12   37   38                                             
CONECT   12   13   14   11   39                                             
CONECT   13   12   40   41   42                                             
CONECT   14   12   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14                                                            
CONECT   18   10   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   43                                                       
CONECT   21    2   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    2                                                            
CONECT   29    3                                                            
CONECT   30    3                                                            
CONECT   31    4                                                            
CONECT   32    5                                                            
CONECT   33    9                                                            
CONECT   34    9                                                            
CONECT   35    9                                                            
CONECT   36   10                                                            
CONECT   37   11                                                            
CONECT   38   11                                                            
CONECT   39   12                                                            
CONECT   40   13                                                            
CONECT   41   13                                                            
CONECT   42   13                                                            
CONECT   43   20                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   84    0
END

RDKit          3D

43 42  0  0  0  0  0  0  0  0999 V2000
    3.7333    1.1124    3.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5819    2.0067    2.4499 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8211    1.1758    1.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8280    0.0889    0.8726 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9905    0.1057   -0.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0580   -1.0260   -0.4026 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2894   -2.1431    0.0564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0871   -0.7828   -1.1327 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6420    0.5532   -1.3359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8608   -1.9022   -1.7304 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0099   -2.8226   -2.6381 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7297   -2.0939   -3.7985 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3021   -1.6044   -4.8339 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8601   -2.9619   -4.4355 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1214   -3.3682   -3.2157 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2330   -4.4879   -5.1312 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7101   -2.0579   -5.7436 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6683   -2.7744   -0.7471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7118   -3.3292   -1.0747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1100   -2.9918    0.4603 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2866    2.8705    2.4664 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3328    4.0359    3.8456 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1387    3.8623    0.9683 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7785    1.9127    2.6364 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.6867    0.5730    3.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7318    1.7015    4.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9357    0.3674    3.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4275    2.7109    2.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9077    1.8472    0.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8075    0.6978    1.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173   -0.7620    1.5541 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9937    0.9186   -0.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1969    1.2936   -0.6681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7174    0.5266   -1.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4705    0.8463   -2.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6315   -1.4322   -2.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7012   -3.3693   -2.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6661   -3.5959   -3.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2144   -1.1977   -3.3890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1687   -1.0645   -5.6600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0133   -0.9060   -4.3832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8764   -2.4354   -5.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1703   -2.6938    0.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
  2 21  1  0
  8  9  1  0
  2  1  1  0
 10 11  1  0
 21 22  1  1
  8  6  1  0
 21 23  1  0
 21 24  1  0
  6  5  1  0
 12 14  1  0
 10 18  1  0
 14 15  1  1
  5  4  2  0
 14 16  1  0
 12 11  1  0
 14 17  1  0
  4  3  1  0
  6  7  2  0
 10  8  1  0
 18 19  2  0
  3  2  1  0
 18 20  1  0
 13 40  1  0
 13 41  1  0
 13 42  1  0
 12 39  1  1
 11 37  1  0
 11 38  1  0
 10 36  1  6
  9 33  1  0
  9 34  1  0
  9 35  1  0
  5 32  1  0
  4 31  1  0
  3 29  1  0
  3 30  1  0
  2 28  1  1
  1 25  1  0
  1 26  1  0
  1 27  1  0
 20 43  1  0
M  END

View in JSmol

Synonyms

Value	Source
Herbacate	Generator

Chemical Formula

C₁₄H₁₉Cl₆NO₃

Average Mass

462.0100 Da

Monoisotopic Mass

458.94961 Da

IUPAC Name

(2S,4S)-5,5,5-trichloro-4-methyl-2-[(2E,5S)-6,6,6-trichloro-N,5-dimethylhex-2-enamido]pentanoic acid

Traditional Name

(2S,4S)-5,5,5-trichloro-4-methyl-2-[(2E,5S)-6,6,6-trichloro-N,5-dimethylhex-2-enamido]pentanoic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)[C@@]([H])(N(C(=O)C(\[H])=C(/[H])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/C14H19Cl6NO3/c1-8(13(15,16)17)5-4-6-11(22)21(3)10(12(23)24)7-9(2)14(18,19)20/h4,6,8-10H,5,7H2,1-3H3,(H,23,24)/b6-4+/t8-,9-,10-/m0/s1

InChI Key

FYSJFLMSVGZPJE-ZNSGJFPESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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, 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 herbacea	JEOL database	MacMillan, J. B., et al, J. Nat. Prod. 63, 155 (2000)
Lamellodysidea herbacea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-L-alpha-amino acids

Alternative Parents

Substituents

N-acyl-l-alpha-amino acid
Branched fatty acid
Halogenated fatty acid
Methyl-branched fatty acid
N-acyl-amine
Fatty acyl
Tertiary carboxylic acid amide
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Alkyl halide
Alkyl chloride
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	4.65	ALOGPS
logP	4.83	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Acidic)	3.32	ChemAxon
pKa (Strongest Basic)	-0.33	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.61 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	103.31 m³·mol⁻¹	ChemAxon
Polarizability	40.95 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

8799268

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10623904

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

MacMillan JB, Molinski TF: Herbacic acid, a simple prototype of 5,5,5-trichloroleucine metabolites from the sponge Dysidea herbacea. J Nat Prod. 2000 Jan;63(1):155-7. doi: 10.1021/np990468j. [PubMed:10650102 ]
MacMillan, J. B., et al. (2000). MacMillan, J. B., et al, J. Nat. Prod. 63, 155 (2000). J. Nat. Prod..

Showing NP-Card for herbacic acid (NP0039200)

MOL for NP0039200 (herbacic acid)

3D MOL for NP0039200 (herbacic acid)

3D SDF for NP0039200 (herbacic acid)

3D-SDF for NP0039200 (herbacic acid)

PDB for NP0039200 (herbacic acid)

3D PDB for NP0039200 (herbacic acid)

SMILES for NP0039200 (herbacic acid)

INCHI for NP0039200 (herbacic acid)

Structure for NP0039200 (herbacic acid)

3D Structure for NP0039200 (herbacic acid)