NP-MRD: Showing NP-Card for Perquinoline B (NP0020084)

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Record Information

Version

2.0

Created at

2021-01-06 05:34:57 UTC

Updated at

2021-07-15 17:32:43 UTC

NP-MRD ID

NP0020084

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Perquinoline B

Provided By

NPAtlas

Description

3-[({10-Amino-10-benzyl-7,9,10a-trihydroxy-3-oxo-1H,2H,3H,5H,10H,10aH-pyrrolo[1,2-b]isoquinolin-5-yl}(hydroxy)methylidene)amino]propanoic acid belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond. Perquinoline B is found in Streptomyces. Based on a literature review very few articles have been published on 3-[({10-amino-10-benzyl-7,9,10a-trihydroxy-3-oxo-1H,2H,3H,5H,10H,10aH-pyrrolo[1,2-b]isoquinolin-5-yl}(hydroxy)methylidene)amino]propanoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242120263D          

 58 61  0  0  0  0            999 V2000
   -3.0594   -0.5732   -1.2343 N   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8265    0.0003   -0.6477 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1262    1.4037   -0.2932 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1823    1.6738    0.7090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8549    1.8649    2.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8095    2.1161    2.9832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1465    2.1912    2.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4818    2.0048    1.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5132    1.7498    0.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6772   -0.1143   -1.5779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8930   -0.1892   -2.9301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1328   -0.1836   -3.5392 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1866   -0.2814   -3.8278 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788   -0.2979   -3.3609 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5376   -0.3888   -4.2555 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6651   -0.2207   -1.9792 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8518   -0.0769    0.3916 C   0  0  2  0  0  0  0  0  0  0  0  0
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    3.3672    0.2795    0.5418 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7072   -0.1444    0.8503 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7001    0.9421    0.5587 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0843    0.5678    0.8537 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9856    1.4189    0.6389 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1697   -1.9671    1.9199 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.8902    2.3945    3.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
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  2  1  1  6  0  0  0
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  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
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  8  9  2  0  0  0  0
  2 10  1  0  0  0  0
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  9  4  1  0  0  0  0
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M  END

     RDKit          3D

 58 61  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242120263D          

 58 61  0  0  0  0            999 V2000
   -3.0594   -0.5732   -1.2343 N   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8265    0.0003   -0.6477 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.1697   -1.9671    1.9199 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801   -2.0691    2.9381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2395   -2.9618    1.5340 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7014   -2.3797    0.1874 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5461   -0.8603    0.5283 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3818   -0.6937    1.5979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6998   -0.7085   -0.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5557    0.1027   -1.8423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2129    1.9290    0.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4110    1.9563   -1.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7818    1.8177    2.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095    2.2627    4.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8902    2.3945    3.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5278    2.0595    1.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8258    1.6180   -0.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2983   -0.2378   -4.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0250   -0.3411   -4.9018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8330   -1.3529   -4.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6724   -0.2382   -1.6128 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8052    0.9399    0.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140    1.2376    0.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7136   -0.4626    1.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0030   -1.0321    0.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6278    1.1822   -0.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4631    1.8453    1.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9572   -0.8020    2.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1021   -2.9112    2.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8171   -3.9701    1.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0214   -2.6463   -0.6323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7483   -2.6159   -0.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9239   -0.8533    2.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  2 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32  2  1  0  0  0  0
  9  4  1  0  0  0  0
 17 10  1  0  0  0  0
 32 27  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  3 36  1  0  0  0  0
  3 37  1  0  0  0  0
  5 38  1  0  0  0  0
  6 39  1  0  0  0  0
  7 40  1  0  0  0  0
  8 41  1  0  0  0  0
  9 42  1  0  0  0  0
 12 43  1  0  0  0  0
 13 44  1  0  0  0  0
 15 45  1  0  0  0  0
 16 46  1  0  0  0  0
 18 47  1  1  0  0  0
 21 48  1  0  0  0  0
 22 49  1  0  0  0  0
 22 50  1  0  0  0  0
 23 51  1  0  0  0  0
 23 52  1  0  0  0  0
 26 53  1  0  0  0  0
 30 54  1  0  0  0  0
 30 55  1  0  0  0  0
 31 56  1  0  0  0  0
 31 57  1  0  0  0  0
 33 58  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0020084

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])C([H])([H])N([H])C(=O)[C@]1([H])N2C(=O)C([H])([H])C([H])([H])[C@]2(O[H])[C@](N([H])[H])(C2=C(O[H])C([H])=C(O[H])C([H])=C12)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H25N3O7/c24-22(12-13-4-2-1-3-5-13)19-15(10-14(27)11-16(19)28)20(21(32)25-9-7-18(30)31)26-17(29)6-8-23(22,26)33/h1-5,10-11,20,27-28,33H,6-9,12,24H2,(H,25,32)(H,30,31)/t20-,22-,23+/m1/s1

> <INCHI_KEY>
XHJZZGRZEGUFCM-UHFFFAOYSA-N

> <FORMULA>
C23H25N3O7

> <MOLECULAR_WEIGHT>
455.467

> <EXACT_MASS>
455.169250157

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
46.15392600181014

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(5R,10R,10aS)-10-amino-10-benzyl-7,9,10a-trihydroxy-3-oxo-1H,2H,3H,5H,10H,10aH-pyrrolo[1,2-b]isoquinolin-5-yl]formamido}propanoic acid

> <ALOGPS_LOGP>
-0.10

> <JCHEM_LOGP>
-2.092580466691098

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.882048171173819

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.214112528251547

> <JCHEM_PKA_STRONGEST_BASIC>
8.870327454165162

> <JCHEM_POLAR_SURFACE_AREA>
173.42

> <JCHEM_REFRACTIVITY>
115.74149999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.94e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(5R,10R,10aS)-10-amino-10-benzyl-7,9,10a-trihydroxy-3-oxo-1H,2H,5H-pyrrolo[1,2-b]isoquinolin-5-yl]formamido}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 58 61  0  0  0  0  0  0  0  0999 V2000
   -3.0594   -0.5732   -1.2343 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8265    0.0003   -0.6477 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1262    1.4037   -0.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1823    1.6738    0.7090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8549    1.8649    2.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8095    2.1161    2.9832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1465    2.1912    2.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4818    2.0048    1.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5132    1.7498    0.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6772   -0.1143   -1.5779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8930   -0.1892   -2.9301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1328   -0.1836   -3.5392 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1866   -0.2814   -3.8278 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788   -0.2979   -3.3609 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5376   -0.3888   -4.2555 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6651   -0.2207   -1.9792 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6163   -0.1313   -1.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8518   -0.0769    0.3916 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2264   -0.5594    0.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4451   -1.7025    1.1760 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3672    0.2795    0.5418 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7072   -0.1444    0.8503 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7001    0.9421    0.5587 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0843    0.5678    0.8537 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9856    1.4189    0.6389 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4836   -0.6631    1.3562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1626   -0.9276    0.9571 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1697   -1.9671    1.9199 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801   -2.0691    2.9381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2395   -2.9618    1.5340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7014   -2.3797    0.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5461   -0.8603    0.5283 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3818   -0.6937    1.5979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6998   -0.7085   -0.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5557    0.1027   -1.8423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2129    1.9290    0.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4110    1.9563   -1.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7818    1.8177    2.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095    2.2627    4.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8902    2.3945    3.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5278    2.0595    1.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8258    1.6180   -0.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2983   -0.2378   -4.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0250   -0.3411   -4.9018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8330   -1.3529   -4.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6724   -0.2382   -1.6128 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8052    0.9399    0.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140    1.2376    0.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7136   -0.4626    1.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0030   -1.0321    0.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6278    1.1822   -0.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4631    1.8453    1.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9572   -0.8020    2.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1021   -2.9112    2.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8171   -3.9701    1.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0214   -2.6463   -0.6323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7483   -2.6159   -0.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9239   -0.8533    2.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 18 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  1
 32  2  1  0
  9  4  1  0
 17 10  1  0
 32 27  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  3 37  1  0
  5 38  1  0
  6 39  1  0
  7 40  1  0
  8 41  1  0
  9 42  1  0
 12 43  1  0
 13 44  1  0
 15 45  1  0
 16 46  1  0
 18 47  1  1
 21 48  1  0
 22 49  1  0
 22 50  1  0
 23 51  1  0
 23 52  1  0
 26 53  1  0
 30 54  1  0
 30 55  1  0
 31 56  1  0
 31 57  1  0
 33 58  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  N   UNK     0      -3.059  -0.573  -1.234  0.00  0.00           N+0
HETATM    2  C   UNK     0      -1.827   0.000  -0.648  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.126   1.404  -0.293  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.182   1.674   0.709  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.855   1.865   2.047  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.809   2.116   2.983  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.146   2.191   2.635  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.482   2.005   1.314  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.513   1.750   0.364  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.677  -0.114  -1.578  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.893  -0.189  -2.930  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.133  -0.184  -3.539  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.187  -0.281  -3.828  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.479  -0.298  -3.361  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.538  -0.389  -4.255  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.665  -0.221  -1.979  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.616  -0.131  -1.108  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.852  -0.077   0.392  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.226  -0.559   0.725  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.445  -1.702   1.176  0.00  0.00           O+0
HETATM   21  N   UNK     0       3.367   0.280   0.542  0.00  0.00           N+0
HETATM   22  C   UNK     0       4.707  -0.144   0.850  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.700   0.942   0.559  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.084   0.568   0.854  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.986   1.419   0.639  0.00  0.00           O+0
HETATM   26  O   UNK     0       7.484  -0.663   1.356  0.00  0.00           O+0
HETATM   27  N   UNK     0      -0.163  -0.928   0.957  0.00  0.00           N+0
HETATM   28  C   UNK     0      -0.170  -1.967   1.920  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.580  -2.069   2.938  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.240  -2.962   1.534  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.701  -2.380   0.187  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.546  -0.860   0.528  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.382  -0.694   1.598  0.00  0.00           O+0
HETATM   34  H   UNK     0      -3.700  -0.709  -0.395  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.556   0.103  -1.842  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.213   1.929   0.120  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.411   1.956  -1.244  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.782   1.818   2.325  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.510   2.263   4.042  0.00  0.00           H+0
HETATM   40  H   UNK     0      -5.890   2.394   3.411  0.00  0.00           H+0
HETATM   41  H   UNK     0      -6.528   2.059   1.015  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.826   1.618  -0.693  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.298  -0.238  -4.524  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.025  -0.341  -4.902  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.833  -1.353  -4.476  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.672  -0.238  -1.613  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.805   0.940   0.755  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.214   1.238   0.173  0.00  0.00           H+0
HETATM   49  H   UNK     0       4.714  -0.463   1.912  0.00  0.00           H+0
HETATM   50  H   UNK     0       5.003  -1.032   0.237  0.00  0.00           H+0
HETATM   51  H   UNK     0       5.628   1.182  -0.522  0.00  0.00           H+0
HETATM   52  H   UNK     0       5.463   1.845   1.187  0.00  0.00           H+0
HETATM   53  H   UNK     0       7.957  -0.802   2.221  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.102  -2.911   2.204  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.817  -3.970   1.395  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.021  -2.646  -0.632  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.748  -2.616  -0.029  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.924  -0.853   2.457  0.00  0.00           H+0
CONECT    1    2   34   35                                                  
CONECT    2    1    3   10   32                                             
CONECT    3    2    4   36   37                                             
CONECT    4    3    5    9                                                  
CONECT    5    4    6   38                                                  
CONECT    6    5    7   39                                                  
CONECT    7    6    8   40                                                  
CONECT    8    7    9   41                                                  
CONECT    9    8    4   42                                                  
CONECT   10    2   11   17                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11   43                                                       
CONECT   13   11   14   44                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   45                                                       
CONECT   16   14   17   46                                                  
CONECT   17   16   18   10                                                  
CONECT   18   17   19   27   47                                             
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   48                                                  
CONECT   22   21   23   49   50                                             
CONECT   23   22   24   51   52                                             
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   53                                                       
CONECT   27   18   28   32                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   54   55                                             
CONECT   31   30   32   56   57                                             
CONECT   32   31   33    2   27                                             
CONECT   33   32   58                                                       
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    3                                                            
CONECT   37    3                                                            
CONECT   38    5                                                            
CONECT   39    6                                                            
CONECT   40    7                                                            
CONECT   41    8                                                            
CONECT   42    9                                                            
CONECT   43   12                                                            
CONECT   44   13                                                            
CONECT   45   15                                                            
CONECT   46   16                                                            
CONECT   47   18                                                            
CONECT   48   21                                                            
CONECT   49   22                                                            
CONECT   50   22                                                            
CONECT   51   23                                                            
CONECT   52   23                                                            
CONECT   53   26                                                            
CONECT   54   30                                                            
CONECT   55   30                                                            
CONECT   56   31                                                            
CONECT   57   31                                                            
CONECT   58   33                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  122    0
END

RDKit          3D

58 61  0  0  0  0  0  0  0  0999 V2000
   -3.0594   -0.5732   -1.2343 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8265    0.0003   -0.6477 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1262    1.4037   -0.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1823    1.6738    0.7090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8549    1.8649    2.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8095    2.1161    2.9832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1465    2.1912    2.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4818    2.0048    1.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5132    1.7498    0.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6772   -0.1143   -1.5779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8930   -0.1892   -2.9301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1328   -0.1836   -3.5392 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1866   -0.2814   -3.8278 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788   -0.2979   -3.3609 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5376   -0.3888   -4.2555 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6651   -0.2207   -1.9792 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6163   -0.1313   -1.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8518   -0.0769    0.3916 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2264   -0.5594    0.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4451   -1.7025    1.1760 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3672    0.2795    0.5418 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7072   -0.1444    0.8503 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7001    0.9421    0.5587 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0843    0.5678    0.8537 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9856    1.4189    0.6389 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4836   -0.6631    1.3562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1626   -0.9276    0.9571 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1697   -1.9671    1.9199 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801   -2.0691    2.9381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2395   -2.9618    1.5340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7014   -2.3797    0.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5461   -0.8603    0.5283 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3818   -0.6937    1.5979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6998   -0.7085   -0.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5557    0.1027   -1.8423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2129    1.9290    0.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4110    1.9563   -1.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7818    1.8177    2.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095    2.2627    4.0420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8902    2.3945    3.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5278    2.0595    1.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8258    1.6180   -0.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2983   -0.2378   -4.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0250   -0.3411   -4.9018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8330   -1.3529   -4.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6724   -0.2382   -1.6128 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8052    0.9399    0.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140    1.2376    0.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7136   -0.4626    1.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0030   -1.0321    0.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6278    1.1822   -0.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4631    1.8453    1.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9572   -0.8020    2.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1021   -2.9112    2.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8171   -3.9701    1.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0214   -2.6463   -0.6323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7483   -2.6159   -0.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9239   -0.8533    2.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 18 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  1
 32  2  1  0
  9  4  1  0
 17 10  1  0
 32 27  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  3 37  1  0
  5 38  1  0
  6 39  1  0
  7 40  1  0
  8 41  1  0
  9 42  1  0
 12 43  1  0
 13 44  1  0
 15 45  1  0
 16 46  1  0
 18 47  1  1
 21 48  1  0
 22 49  1  0
 22 50  1  0
 23 51  1  0
 23 52  1  0
 26 53  1  0
 30 54  1  0
 30 55  1  0
 31 56  1  0
 31 57  1  0
 33 58  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
3-[({10-amino-10-benzyl-7,9,10a-trihydroxy-3-oxo-1H,2H,3H,5H,10H,10ah-pyrrolo[1,2-b]isoquinolin-5-yl}(hydroxy)methylidene)amino]propanoate	Generator

Chemical Formula

C₂₃H₂₅N₃O₇

Average Mass

455.4670 Da

Monoisotopic Mass

455.16925 Da

IUPAC Name

3-{[(5R,10R,10aS)-10-amino-10-benzyl-7,9,10a-trihydroxy-3-oxo-1H,2H,3H,5H,10H,10aH-pyrrolo[1,2-b]isoquinolin-5-yl]formamido}propanoic acid

Traditional Name

3-{[(5R,10R,10aS)-10-amino-10-benzyl-7,9,10a-trihydroxy-3-oxo-1H,2H,5H-pyrrolo[1,2-b]isoquinolin-5-yl]formamido}propanoic acid

CAS Registry Number

Not Available

SMILES

NC1(CC2=CC=CC=C2)C2=C(O)C=C(O)C=C2C(N2C(=O)CCC12O)C(=O)NCCC(O)=O

InChI Identifier

InChI=1S/C23H25N3O7/c24-22(12-13-4-2-1-3-5-13)19-15(10-14(27)11-16(19)28)20(21(32)25-9-7-18(30)31)26-17(29)6-8-23(22,26)33/h1-5,10-11,20,27-28,33H,6-9,12,24H2,(H,25,32)(H,30,31)

InChI Key

XHJZZGRZEGUFCM-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Streptomyces	NPAtlas	31310031

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Hybrid peptides

Direct Parent

Hybrid peptides

Alternative Parents

Substituents

Hybrid peptide
Benzylisoquinoline
Delta amino acid or derivatives
Beta amino acid or derivatives
Tetrahydroisoquinoline
Alpha-amino acid or derivatives
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Benzenoid
N-alkylpyrrolidine
2-pyrrolidone
Pyrrolidone
Monocyclic benzene moiety
Tertiary carboxylic acid amide
Pyrrolidine
Amino acid
Secondary carboxylic acid amide
Lactam
Carboxamide group
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Alkanolamine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.1	ALOGPS
logP	-2.1	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.21	ChemAxon
pKa (Strongest Basic)	8.87	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	173.42 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	115.74 m³·mol⁻¹	ChemAxon
Polarizability	46.15 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

NPAtlas ID

NPA025692

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

146682171

PDB ID

Not Available

ChEBI ID

156392

Good Scents ID

Not Available

References

General References

Showing NP-Card for Perquinoline B (NP0020084)

MOL for NP0020084 (Perquinoline B)

3D MOL for NP0020084 (Perquinoline B)

3D SDF for NP0020084 (Perquinoline B)

3D-SDF for NP0020084 (Perquinoline B)

PDB for NP0020084 (Perquinoline B)

3D PDB for NP0020084 (Perquinoline B)

SMILES for NP0020084 (Perquinoline B)

INCHI for NP0020084 (Perquinoline B)

Structure for NP0020084 (Perquinoline B)

3D Structure for NP0020084 (Perquinoline B)