NP-MRD: Showing NP-Card for 3-[(6-amino-2,4-dihydroxy-4,5,6,7-tetrahydro-3h-azepin-3-yl)-c-hydroxycarbonimidoyl]-3-[({3-[carboxy(chloro)methyl]-2-chloro-2-(1-chlorobutyl)cyclopropyl}(hydroxy)methylidene)amino]propanoic acid (NP0160228)

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Record Information

Version

2.0

Created at

2022-09-02 18:08:07 UTC

Updated at

2022-09-02 18:08:07 UTC

NP-MRD ID

NP0160228

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[(6-amino-2,4-dihydroxy-4,5,6,7-tetrahydro-3h-azepin-3-yl)-c-hydroxycarbonimidoyl]-3-[({3-[carboxy(chloro)methyl]-2-chloro-2-(1-chlorobutyl)cyclopropyl}(hydroxy)methylidene)amino]propanoic acid

Description

Peritoxin B belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. 3-[(6-amino-2,4-dihydroxy-4,5,6,7-tetrahydro-3h-azepin-3-yl)-c-hydroxycarbonimidoyl]-3-[({3-[carboxy(chloro)methyl]-2-chloro-2-(1-chlorobutyl)cyclopropyl}(hydroxy)methylidene)amino]propanoic acid is found in Periconia circinata. Based on a literature review very few articles have been published on Peritoxin B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022220082D          

 35 36  0  0  0  0            999 V2000
   -2.1697    0.7301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0264   -0.0824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6584   -0.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5151   -1.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7399   -1.7073    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1471   -1.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7791   -1.4252    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.7346   -2.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0201   -3.0824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3057   -2.6699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0201   -3.9074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3057   -4.3199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3057   -5.1449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5912   -5.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1233   -5.1449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5912   -6.3824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5912   -3.9074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5912   -3.0824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1233   -4.3199    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8377   -3.9074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7761   -3.0847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0081   -2.7833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3809   -2.5236    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1966   -2.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6091   -3.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4318   -3.2994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3077   -4.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5194   -4.3722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3964   -5.1880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5596   -2.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2741   -3.0824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9886   -2.6699    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2741   -3.9074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5596   -4.3199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9886   -4.3199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  4  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  4  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 20 28  1  0  0  0  0
 28 29  1  0  0  0  0
  8 30  1  0  0  0  0
  6 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END

     RDKit          3D

 64 65  0  0  0  0  0  0  0  0999 V2000
   -5.4391    3.0058   -0.9954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5059    1.5441   -0.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3943    0.7373   -1.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4089   -0.6729   -0.6918 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9443   -1.4294   -1.1051 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.8827   -1.0599    0.6223 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0679   -2.8544    0.9088 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3876   -0.6284    0.9131 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4068   -1.6863    0.9549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5488   -2.8098    1.7372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3109   -1.6847    0.2714 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1519   -0.6889   -0.6309 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2261   -1.0669   -2.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2418   -0.0481   -3.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4356    0.0323   -3.4051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6536    0.8663   -3.5609 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6479   -0.7407   -0.5975 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2328   -1.9408   -0.9706 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3640    0.2700   -0.2424 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7852    0.2261   -0.2089 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4290    1.2332   -1.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6460    2.1867   -1.7139 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6916    1.3209   -1.3176 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7934    0.5134   -0.8386 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8207    0.4528    0.6704 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9014    1.7841    1.2089 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6718   -0.3407    1.2303 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3672    0.3785    1.1743 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5060    1.6902    1.5628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4803   -0.2716    1.7662 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8259   -0.6823    3.1532 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2782   -2.2195    3.7295 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.3309   -0.6517    3.2568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9653    0.0519    4.0479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0283   -1.4784    2.3945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0825    3.1780   -1.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6923    3.6344   -0.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3667    3.1752   -1.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5140    1.1882   -0.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6110    1.4911    0.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4062    1.2366   -1.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5849    0.7338   -2.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6465   -1.1755   -1.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0868    0.1890    0.1473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5800   -3.7149    1.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1392    0.3354   -0.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3290   -1.1770   -2.0777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2842   -2.0194   -2.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6096    1.0124   -4.5728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3029   -2.2212   -1.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1084   -0.7805   -0.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8401    3.1771   -1.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7459    0.9040   -1.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5868   -0.5328   -1.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7538   -0.0822    0.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0364    1.7397    2.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7722    2.2263    0.8426 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412   -1.3144    0.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9088   -0.5590    2.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6641   -0.1103    1.8796 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5662    2.3317    0.8292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7596    0.8600    1.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4994    0.1061    3.9048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9043   -1.1528    2.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  1
  6 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 33 35  1  0
 33 34  2  0
 30  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 16  1  0
 14 15  2  0
 12 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 28  1  0
 28 29  1  0
 28 27  1  0
 27 25  1  0
 25 26  1  0
 25 24  1  0
 24 23  1  0
 23 21  2  0
 21 22  1  0
  8  6  1  0
 21 20  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  0
  2 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  6
 30 62  1  6
 31 63  1  1
 35 64  1  0
  8 44  1  6
 10 45  1  0
 12 46  1  1
 13 47  1  0
 13 48  1  0
 16 49  1  0
 18 50  1  0
 20 51  1  6
 28 60  1  1
 29 61  1  0
 27 58  1  0
 27 59  1  0
 25 55  1  6
 26 56  1  0
 26 57  1  0
 24 53  1  0
 24 54  1  0
 22 52  1  0
M  END


  Mrv1652309022220082D          

 35 36  0  0  0  0            999 V2000
   -2.1697    0.7301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0264   -0.0824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6584   -0.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5151   -1.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7399   -1.7073    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1471   -1.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7791   -1.4252    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.7346   -2.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0201   -3.0824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3057   -2.6699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0201   -3.9074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3057   -4.3199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3057   -5.1449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5912   -5.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1233   -5.1449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5912   -6.3824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5912   -3.9074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5912   -3.0824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1233   -4.3199    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8377   -3.9074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7761   -3.0847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0081   -2.7833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3809   -2.5236    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1966   -2.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6091   -3.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4318   -3.2994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3077   -4.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5194   -4.3722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3964   -5.1880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5596   -2.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2741   -3.0824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9886   -2.6699    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2741   -3.9074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5596   -4.3199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9886   -4.3199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  4  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  4  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 20 28  1  0  0  0  0
 28 29  1  0  0  0  0
  8 30  1  0  0  0  0
  6 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0160228

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(Cl)C1(Cl)C(C(Cl)C(O)=O)C1C(O)=NC(CC(O)=O)C(O)=NC1C(O)CC(N)CN=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H29Cl3N4O8/c1-2-3-10(21)20(23)12(14(22)19(34)35)13(20)17(32)26-8(5-11(29)30)16(31)27-15-9(28)4-7(24)6-25-18(15)33/h7-10,12-15,28H,2-6,24H2,1H3,(H,25,33)(H,26,32)(H,27,31)(H,29,30)(H,34,35)

> <INCHI_KEY>
RSMNHRRWERNDLZ-UHFFFAOYSA-N

> <FORMULA>
C20H29Cl3N4O8

> <MOLECULAR_WEIGHT>
559.82

> <EXACT_MASS>
558.105097

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
51.41624301956176

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(3-amino-5,7-dihydroxy-3,4,5,6-tetrahydro-2H-azepin-6-yl)-C-hydroxycarbonimidoyl]-3-[({3-[carboxy(chloro)methyl]-2-chloro-2-(1-chlorobutyl)cyclopropyl}(hydroxy)methylidene)amino]propanoic acid

> <ALOGPS_LOGP>
-0.51

> <JCHEM_LOGP>
-2.148132549109413

> <ALOGPS_LOGS>
-3.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
2.864998116671123

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2955848668577419

> <JCHEM_PKA_STRONGEST_BASIC>
9.690448435973325

> <JCHEM_POLAR_SURFACE_AREA>
218.61999999999998

> <JCHEM_REFRACTIVITY>
123.21300000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(6-amino-2,4-dihydroxy-4,5,6,7-tetrahydro-3H-azepin-3-yl)-C-hydroxycarbonimidoyl]-3-[({3-[carboxy(chloro)methyl]-2-chloro-2-(1-chlorobutyl)cyclopropyl}(hydroxy)methylidene)amino]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.050   1.363   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.783  -0.154   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.962  -1.144   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.695  -2.660   0.000  0.00  0.00           C+0
HETATM    5 Cl   UNK     0      -3.248  -3.187   0.000  0.00  0.00          Cl+0
HETATM    6  C   UNK     0      -5.875  -3.650   0.000  0.00  0.00           C+0
HETATM    7 Cl   UNK     0      -7.054  -2.660   0.000  0.00  0.00          Cl+0
HETATM    8  C   UNK     0      -5.105  -4.984   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.771  -5.754   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.437  -4.984   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      -3.771  -7.294   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -2.437  -8.064   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.437  -9.604   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.104 -10.374   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.230  -9.604   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.104 -11.914   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.104  -7.294   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.104  -5.754   0.000  0.00  0.00           O+0
HETATM   19  N   UNK     0       0.230  -8.064   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       1.564  -7.294   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.449  -5.758   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.015  -5.196   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0       2.578  -4.711   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       4.100  -4.940   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.870  -6.274   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       6.406  -6.159   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       4.308  -7.707   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.836  -8.161   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.607  -9.684   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -6.645  -4.984   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -7.978  -5.754   0.000  0.00  0.00           C+0
HETATM   32 Cl   UNK     0      -9.312  -4.984   0.000  0.00  0.00          Cl+0
HETATM   33  C   UNK     0      -7.978  -7.294   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -6.645  -8.064   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -9.312  -8.064   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8   30                                             
CONECT    7    6                                                            
CONECT    8    6    9   30                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   12   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   28                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   20   29                                                  
CONECT   29   28                                                            
CONECT   30    8    6   31                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₉Cl₃N₄O₈

Average Mass

559.8200 Da

Monoisotopic Mass

558.10510 Da

IUPAC Name

3-[(3-amino-5,7-dihydroxy-3,4,5,6-tetrahydro-2H-azepin-6-yl)-C-hydroxycarbonimidoyl]-3-[({3-[carboxy(chloro)methyl]-2-chloro-2-(1-chlorobutyl)cyclopropyl}(hydroxy)methylidene)amino]propanoic acid

Traditional Name

3-[(6-amino-2,4-dihydroxy-4,5,6,7-tetrahydro-3H-azepin-3-yl)-C-hydroxycarbonimidoyl]-3-[({3-[carboxy(chloro)methyl]-2-chloro-2-(1-chlorobutyl)cyclopropyl}(hydroxy)methylidene)amino]propanoic acid

CAS Registry Number

Not Available

SMILES

CCCC(Cl)C1(Cl)C(C(Cl)C(O)=O)C1C(O)=NC(CC(O)=O)C(O)=NC1C(O)CC(N)CN=C1O

InChI Identifier

InChI=1S/C20H29Cl3N4O8/c1-2-3-10(21)20(23)12(14(22)19(34)35)13(20)17(32)26-8(5-11(29)30)16(31)27-15-9(28)4-7(24)6-25-18(15)33/h7-10,12-15,28H,2-6,24H2,1H3,(H,25,33)(H,26,32)(H,27,31)(H,29,30)(H,34,35)

InChI Key

RSMNHRRWERNDLZ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Periconia circinata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Aspartic acid or derivatives
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Caprolactam
Hydroxy fatty acid
Heterocyclic fatty acid
Halogenated fatty acid
Azepane
Cyclopropanecarboxylic acid or derivatives
Dicarboxylic acid or derivatives
Fatty amide
Fatty acid
Fatty acyl
N-acyl-amine
Alpha-halocarboxylic acid
Alpha-halocarboxylic acid or derivatives
Amino acid
Amino acid or derivatives
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Lactam
Azacycle
Carboxylic acid
Organoheterocyclic compound
Organohalogen compound
Alkyl halide
Organic nitrogen compound
Alkyl chloride
Carbonyl group
Primary amine
Hydrocarbon derivative
Amine
Alcohol
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Primary aliphatic amine
Organochloride
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	-0.51	ALOGPS
logP	-2.1	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	1.3	ChemAxon
pKa (Strongest Basic)	9.69	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	218.62 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	123.21 m³·mol⁻¹	ChemAxon
Polarizability	51.42 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

109462

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122791

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[(6-amino-2,4-dihydroxy-4,5,6,7-tetrahydro-3h-azepin-3-yl)-c-hydroxycarbonimidoyl]-3-[({3-[carboxy(chloro)methyl]-2-chloro-2-(1-chlorobutyl)cyclopropyl}(hydroxy)methylidene)amino]propanoic acid (NP0160228)

MOL for NP0160228 (3-[(6-amino-2,4-dihydroxy-4,5,6,7-tetrahydro-3h-azepin-3-yl)-c-hydroxycarbonimidoyl]-3-[({3-[carboxy(chloro)methyl]-2-chloro-2-(1-chlorobutyl)cyclopropyl}(hydroxy)methylidene)amino]propanoic acid)

3D MOL for NP0160228 (3-[(6-amino-2,4-dihydroxy-4,5,6,7-tetrahydro-3h-azepin-3-yl)-c-hydroxycarbonimidoyl]-3-[({3-[carboxy(chloro)methyl]-2-chloro-2-(1-chlorobutyl)cyclopropyl}(hydroxy)methylidene)amino]propanoic acid)

3D SDF for NP0160228 (3-[(6-amino-2,4-dihydroxy-4,5,6,7-tetrahydro-3h-azepin-3-yl)-c-hydroxycarbonimidoyl]-3-[({3-[carboxy(chloro)methyl]-2-chloro-2-(1-chlorobutyl)cyclopropyl}(hydroxy)methylidene)amino]propanoic acid)

3D-SDF for NP0160228 (3-[(6-amino-2,4-dihydroxy-4,5,6,7-tetrahydro-3h-azepin-3-yl)-c-hydroxycarbonimidoyl]-3-[({3-[carboxy(chloro)methyl]-2-chloro-2-(1-chlorobutyl)cyclopropyl}(hydroxy)methylidene)amino]propanoic acid)

PDB for NP0160228 (3-[(6-amino-2,4-dihydroxy-4,5,6,7-tetrahydro-3h-azepin-3-yl)-c-hydroxycarbonimidoyl]-3-[({3-[carboxy(chloro)methyl]-2-chloro-2-(1-chlorobutyl)cyclopropyl}(hydroxy)methylidene)amino]propanoic acid)

3D PDB for NP0160228 (3-[(6-amino-2,4-dihydroxy-4,5,6,7-tetrahydro-3h-azepin-3-yl)-c-hydroxycarbonimidoyl]-3-[({3-[carboxy(chloro)methyl]-2-chloro-2-(1-chlorobutyl)cyclopropyl}(hydroxy)methylidene)amino]propanoic acid)

SMILES for NP0160228 (3-[(6-amino-2,4-dihydroxy-4,5,6,7-tetrahydro-3h-azepin-3-yl)-c-hydroxycarbonimidoyl]-3-[({3-[carboxy(chloro)methyl]-2-chloro-2-(1-chlorobutyl)cyclopropyl}(hydroxy)methylidene)amino]propanoic acid)

INCHI for NP0160228 (3-[(6-amino-2,4-dihydroxy-4,5,6,7-tetrahydro-3h-azepin-3-yl)-c-hydroxycarbonimidoyl]-3-[({3-[carboxy(chloro)methyl]-2-chloro-2-(1-chlorobutyl)cyclopropyl}(hydroxy)methylidene)amino]propanoic acid)

Structure for NP0160228 (3-[(6-amino-2,4-dihydroxy-4,5,6,7-tetrahydro-3h-azepin-3-yl)-c-hydroxycarbonimidoyl]-3-[({3-[carboxy(chloro)methyl]-2-chloro-2-(1-chlorobutyl)cyclopropyl}(hydroxy)methylidene)amino]propanoic acid)

3D Structure for NP0160228 (3-[(6-amino-2,4-dihydroxy-4,5,6,7-tetrahydro-3h-azepin-3-yl)-c-hydroxycarbonimidoyl]-3-[({3-[carboxy(chloro)methyl]-2-chloro-2-(1-chlorobutyl)cyclopropyl}(hydroxy)methylidene)amino]propanoic acid)