NP-MRD: Showing NP-Card for Perquinoline A (NP0020083)

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Record Information

Version

2.0

Created at

2021-01-06 05:34:48 UTC

Updated at

2021-07-15 17:32:43 UTC

NP-MRD ID

NP0020083

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Perquinoline A

Provided By

NPAtlas

Description

4-[({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]butanoic acid belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached. Perquinoline A is found in Streptomyces. Based on a literature review very few articles have been published on 4-[({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]butanoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242120263D          

 61 64  0  0  0  0            999 V2000
   -2.0400   -1.4301    0.9026 N   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8764   -0.2204    0.0685 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0872    0.0488   -0.6965 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3793    0.2302   -0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0740    1.3863   -0.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3044    1.5628    0.5628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8627    0.5135    1.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1618   -0.6782    1.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0748    0.7331    0.7870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3566    2.0285    1.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5625    2.5711    0.8316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4903    2.8705    1.8325 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7381    2.3890    2.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6443    3.1851    2.8628 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0781    1.0966    1.8432 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5106   -0.0395    0.4349 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.8825    0.9669   -1.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2698   -0.7319   -1.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7207    2.2802   -0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.8257    0.5837    1.7550 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8084    3.5044    1.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
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  2  1  1  1  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
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 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
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 34 61  1  0  0  0  0
M  END

     RDKit          3D

 61 64  0  0  0  0  0  0  0  0999 V2000
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   -1.8764   -0.2204    0.0685 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306242120263D          

 61 64  0  0  0  0            999 V2000
   -2.0400   -1.4301    0.9026 N   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8764   -0.2204    0.0685 C   0  0  1  0  0  0  0  0  0  0  0  0
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    4.3871   -1.0695   -0.3516 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0015    0.0388    0.4524 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5106   -0.0395    0.4349 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9684    0.0734   -0.9686 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0452   -0.8807   -1.7737 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3394    1.3535   -1.4107 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1696   -1.4419   -0.4660 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5011   -2.4906   -1.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3079   -3.4426   -1.1662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2547   -2.2971   -2.6428 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4870   -1.5454   -2.0744 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8618   -0.6783   -1.0707 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4566    0.5140   -1.6472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8477   -1.2929    1.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6489   -2.2687    0.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8825    0.9669   -1.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2698   -0.7319   -1.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7207    2.2802   -0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7984    2.4975    0.5232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8257    0.5837    1.7550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6001   -1.5366    1.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4667   -1.8091    0.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8084    3.5044    1.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7680    3.8873    2.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3036    3.7614    2.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0824    0.7854    2.1534 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3856   -1.8677    1.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4039   -0.9313   -1.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7633   -1.0413   -1.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7775   -2.0290    0.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6783    0.0349    1.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7156    1.0485    0.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8104   -1.0300    0.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9436    0.7791    1.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6400    2.1027   -1.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5894   -3.2435   -3.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2659   -1.6323   -3.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9935   -1.0268   -2.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1424   -2.3548   -1.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6575    1.3044   -1.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 18 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33  2  1  0  0  0  0
  9  4  1  0  0  0  0
 17 10  1  0  0  0  0
 33 28  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  3 37  1  0  0  0  0
  3 38  1  0  0  0  0
  5 39  1  0  0  0  0
  6 40  1  0  0  0  0
  7 41  1  0  0  0  0
  8 42  1  0  0  0  0
  9 43  1  0  0  0  0
 12 44  1  0  0  0  0
 13 45  1  0  0  0  0
 15 46  1  0  0  0  0
 16 47  1  0  0  0  0
 18 48  1  1  0  0  0
 21 49  1  0  0  0  0
 22 50  1  0  0  0  0
 22 51  1  0  0  0  0
 23 52  1  0  0  0  0
 23 53  1  0  0  0  0
 24 54  1  0  0  0  0
 24 55  1  0  0  0  0
 27 56  1  0  0  0  0
 31 57  1  0  0  0  0
 31 58  1  0  0  0  0
 32 59  1  0  0  0  0
 32 60  1  0  0  0  0
 34 61  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0020083

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])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/C24H27N3O7/c25-23(13-14-5-2-1-3-6-14)20-16(11-15(28)12-17(20)29)21(22(33)26-10-4-7-19(31)32)27-18(30)8-9-24(23,27)34/h1-3,5-6,11-12,21,28-29,34H,4,7-10,13,25H2,(H,26,33)(H,31,32)/t21-,23+,24-/m1/s1

> <INCHI_KEY>
CDFQOHHGTNUFPU-UHFFFAOYSA-N

> <FORMULA>
C24H27N3O7

> <MOLECULAR_WEIGHT>
469.494

> <EXACT_MASS>
469.184900221

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
47.8250352860205

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-{[(5R,10S,10aR)-10-amino-10-benzyl-7,9,10a-trihydroxy-3-oxo-1H,2H,3H,5H,10H,10aH-pyrrolo[1,2-b]isoquinolin-5-yl]formamido}butanoic acid

> <ALOGPS_LOGP>
-0.03

> <JCHEM_LOGP>
-1.8039084162535488

> <ALOGPS_LOGS>
-3.06

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.882048728407788

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.242059545863688

> <JCHEM_PKA_STRONGEST_BASIC>
8.870327538515173

> <JCHEM_POLAR_SURFACE_AREA>
173.42

> <JCHEM_REFRACTIVITY>
120.49649999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.09e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{[(5R,10S,10aR)-10-amino-10-benzyl-7,9,10a-trihydroxy-3-oxo-1H,2H,5H-pyrrolo[1,2-b]isoquinolin-5-yl]formamido}butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 61 64  0  0  0  0  0  0  0  0999 V2000
   -2.0400   -1.4301    0.9026 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8764   -0.2204    0.0685 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0872    0.0488   -0.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3793    0.2302   -0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0740    1.3863   -0.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3044    1.5628    0.5628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8627    0.5135    1.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1618   -0.6782    1.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9519   -0.8518    0.6228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0748    0.7331    0.7870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3566    2.0285    1.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5625    2.5711    0.8316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4903    2.8705    1.8325 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7381    2.3890    2.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6443    3.1851    2.8628 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0781    1.0966    1.8432 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2164    0.2690    1.1666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6943   -1.1054    0.8495 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1840   -1.1374    0.8278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7919   -1.2603    1.9121 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9537   -1.0358   -0.3573 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3871   -1.0695   -0.3516 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0015    0.0388    0.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5106   -0.0395    0.4349 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9684    0.0734   -0.9686 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0452   -0.8807   -1.7737 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3394    1.3535   -1.4107 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1696   -1.4419   -0.4660 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5011   -2.4906   -1.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3079   -3.4426   -1.1662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2547   -2.2971   -2.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4870   -1.5454   -2.0744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8618   -0.6783   -1.0707 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4566    0.5140   -1.6472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8477   -1.2929    1.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6489   -2.2687    0.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8825    0.9669   -1.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2698   -0.7319   -1.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7207    2.2802   -0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7984    2.4975    0.5232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8257    0.5837    1.7550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6001   -1.5366    1.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4667   -1.8091    0.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8084    3.5044    1.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7680    3.8873    2.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3036    3.7614    2.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0824    0.7854    2.1534 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3856   -1.8677    1.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4039   -0.9313   -1.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7633   -1.0413   -1.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7775   -2.0290    0.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6783    0.0349    1.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7156    1.0485    0.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8104   -1.0300    0.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9436    0.7791    1.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6400    2.1027   -1.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5894   -3.2435   -3.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2659   -1.6323   -3.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9935   -1.0268   -2.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1424   -2.3548   -1.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6575    1.3044   -1.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  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  1  0
 25 26  2  0
 25 27  1  0
 18 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  6
 33  2  1  0
  9  4  1  0
 17 10  1  0
 33 28  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  5 39  1  0
  6 40  1  0
  7 41  1  0
  8 42  1  0
  9 43  1  0
 12 44  1  0
 13 45  1  0
 15 46  1  0
 16 47  1  0
 18 48  1  1
 21 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  0
 24 55  1  0
 27 56  1  0
 31 57  1  0
 31 58  1  0
 32 59  1  0
 32 60  1  0
 34 61  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      -2.040  -1.430   0.903  0.00  0.00           N+0
HETATM    2  C   UNK     0      -1.876  -0.220   0.069  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.087   0.049  -0.697  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.379   0.230  -0.069  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.074   1.386  -0.072  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.304   1.563   0.563  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.863   0.514   1.236  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.162  -0.678   1.246  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.952  -0.852   0.623  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.075   0.733   0.787  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.357   2.029   1.148  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.563   2.571   0.832  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.490   2.870   1.833  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.738   2.389   2.179  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.644   3.185   2.863  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.078   1.097   1.843  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.216   0.269   1.167  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.694  -1.105   0.850  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.184  -1.137   0.828  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.792  -1.260   1.912  0.00  0.00           O+0
HETATM   21  N   UNK     0       2.954  -1.036  -0.357  0.00  0.00           N+0
HETATM   22  C   UNK     0       4.387  -1.069  -0.352  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.002   0.039   0.452  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.511  -0.040   0.435  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.968   0.073  -0.969  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.045  -0.881  -1.774  0.00  0.00           O+0
HETATM   27  O   UNK     0       7.339   1.353  -1.411  0.00  0.00           O+0
HETATM   28  N   UNK     0       0.170  -1.442  -0.466  0.00  0.00           N+0
HETATM   29  C   UNK     0       0.501  -2.491  -1.380  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.308  -3.443  -1.166  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.255  -2.297  -2.643  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.487  -1.545  -2.074  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.862  -0.678  -1.071  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.457   0.514  -1.647  0.00  0.00           O+0
HETATM   35  H   UNK     0      -1.848  -1.293   1.887  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.649  -2.269   0.519  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.882   0.967  -1.348  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.270  -0.732  -1.511  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.721   2.280  -0.609  0.00  0.00           H+0
HETATM   40  H   UNK     0      -6.798   2.498   0.523  0.00  0.00           H+0
HETATM   41  H   UNK     0      -7.826   0.584   1.755  0.00  0.00           H+0
HETATM   42  H   UNK     0      -6.600  -1.537   1.786  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.467  -1.809   0.675  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.808   3.504   1.073  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.768   3.887   2.093  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.304   3.761   2.348  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.082   0.785   2.153  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.386  -1.868   1.573  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.404  -0.931  -1.250  0.00  0.00           H+0
HETATM   50  H   UNK     0       4.763  -1.041  -1.404  0.00  0.00           H+0
HETATM   51  H   UNK     0       4.777  -2.029   0.081  0.00  0.00           H+0
HETATM   52  H   UNK     0       4.678   0.035   1.502  0.00  0.00           H+0
HETATM   53  H   UNK     0       4.716   1.048   0.063  0.00  0.00           H+0
HETATM   54  H   UNK     0       6.810  -1.030   0.868  0.00  0.00           H+0
HETATM   55  H   UNK     0       6.944   0.779   1.048  0.00  0.00           H+0
HETATM   56  H   UNK     0       6.640   2.103  -1.428  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.589  -3.244  -3.093  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.266  -1.632  -3.360  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.994  -1.027  -2.929  0.00  0.00           H+0
HETATM   60  H   UNK     0      -2.142  -2.355  -1.721  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.658   1.304  -1.118  0.00  0.00           H+0
CONECT    1    2   35   36                                                  
CONECT    2    1    3   10   33                                             
CONECT    3    2    4   37   38                                             
CONECT    4    3    5    9                                                  
CONECT    5    4    6   39                                                  
CONECT    6    5    7   40                                                  
CONECT    7    6    8   41                                                  
CONECT    8    7    9   42                                                  
CONECT    9    8    4   43                                                  
CONECT   10    2   11   17                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11   44                                                       
CONECT   13   11   14   45                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   46                                                       
CONECT   16   14   17   47                                                  
CONECT   17   16   18   10                                                  
CONECT   18   17   19   28   48                                             
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   49                                                  
CONECT   22   21   23   50   51                                             
CONECT   23   22   24   52   53                                             
CONECT   24   23   25   54   55                                             
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   56                                                       
CONECT   28   18   29   33                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   57   58                                             
CONECT   32   31   33   59   60                                             
CONECT   33   32   34    2   28                                             
CONECT   34   33   61                                                       
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    3                                                            
CONECT   38    3                                                            
CONECT   39    5                                                            
CONECT   40    6                                                            
CONECT   41    7                                                            
CONECT   42    8                                                            
CONECT   43    9                                                            
CONECT   44   12                                                            
CONECT   45   13                                                            
CONECT   46   15                                                            
CONECT   47   16                                                            
CONECT   48   18                                                            
CONECT   49   21                                                            
CONECT   50   22                                                            
CONECT   51   22                                                            
CONECT   52   23                                                            
CONECT   53   23                                                            
CONECT   54   24                                                            
CONECT   55   24                                                            
CONECT   56   27                                                            
CONECT   57   31                                                            
CONECT   58   31                                                            
CONECT   59   32                                                            
CONECT   60   32                                                            
CONECT   61   34                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  128    0
END

RDKit          3D

61 64  0  0  0  0  0  0  0  0999 V2000
   -2.0400   -1.4301    0.9026 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8764   -0.2204    0.0685 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0872    0.0488   -0.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3793    0.2302   -0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0740    1.3863   -0.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3044    1.5628    0.5628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8627    0.5135    1.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1618   -0.6782    1.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9519   -0.8518    0.6228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0748    0.7331    0.7870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3566    2.0285    1.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5625    2.5711    0.8316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4903    2.8705    1.8325 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7381    2.3890    2.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6443    3.1851    2.8628 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0781    1.0966    1.8432 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2164    0.2690    1.1666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6943   -1.1054    0.8495 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1840   -1.1374    0.8278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7919   -1.2603    1.9121 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9537   -1.0358   -0.3573 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3871   -1.0695   -0.3516 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0015    0.0388    0.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5106   -0.0395    0.4349 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9684    0.0734   -0.9686 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0452   -0.8807   -1.7737 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3394    1.3535   -1.4107 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1696   -1.4419   -0.4660 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5011   -2.4906   -1.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3079   -3.4426   -1.1662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2547   -2.2971   -2.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4870   -1.5454   -2.0744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8618   -0.6783   -1.0707 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4566    0.5140   -1.6472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8477   -1.2929    1.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6489   -2.2687    0.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8825    0.9669   -1.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2698   -0.7319   -1.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7207    2.2802   -0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7984    2.4975    0.5232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8257    0.5837    1.7550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6001   -1.5366    1.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4667   -1.8091    0.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8084    3.5044    1.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7680    3.8873    2.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3036    3.7614    2.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0824    0.7854    2.1534 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3856   -1.8677    1.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4039   -0.9313   -1.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7633   -1.0413   -1.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7775   -2.0290    0.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6783    0.0349    1.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7156    1.0485    0.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8104   -1.0300    0.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9436    0.7791    1.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6400    2.1027   -1.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5894   -3.2435   -3.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2659   -1.6323   -3.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9935   -1.0268   -2.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1424   -2.3548   -1.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6575    1.3044   -1.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  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  1  0
 25 26  2  0
 25 27  1  0
 18 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  6
 33  2  1  0
  9  4  1  0
 17 10  1  0
 33 28  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  5 39  1  0
  6 40  1  0
  7 41  1  0
  8 42  1  0
  9 43  1  0
 12 44  1  0
 13 45  1  0
 15 46  1  0
 16 47  1  0
 18 48  1  1
 21 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  0
 24 55  1  0
 27 56  1  0
 31 57  1  0
 31 58  1  0
 32 59  1  0
 32 60  1  0
 34 61  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
4-[({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]butanoate	Generator

Chemical Formula

C₂₄H₂₇N₃O₇

Average Mass

469.4940 Da

Monoisotopic Mass

469.18490 Da

IUPAC Name

4-{[(5R,10S,10aR)-10-amino-10-benzyl-7,9,10a-trihydroxy-3-oxo-1H,2H,3H,5H,10H,10aH-pyrrolo[1,2-b]isoquinolin-5-yl]formamido}butanoic acid

Traditional Name

4-{[(5R,10S,10aR)-10-amino-10-benzyl-7,9,10a-trihydroxy-3-oxo-1H,2H,5H-pyrrolo[1,2-b]isoquinolin-5-yl]formamido}butanoic 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)NCCCC(O)=O

InChI Identifier

InChI=1S/C24H27N3O7/c25-23(13-14-5-2-1-3-6-14)20-16(11-15(28)12-17(20)29)21(22(33)26-10-4-7-19(31)32)27-18(30)8-9-24(23,27)34/h1-3,5-6,11-12,21,28-29,34H,4,7-10,13,25H2,(H,26,33)(H,31,32)

InChI Key

CDFQOHHGTNUFPU-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 benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Benzylisoquinolines

Direct Parent

Benzylisoquinolines

Alternative Parents

Substituents

Benzylisoquinoline
Delta amino acid or derivatives
Gamma 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
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	-0.03	ALOGPS
logP	-1.8	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.24	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	7	ChemAxon
Refractivity	120.5 m³·mol⁻¹	ChemAxon
Polarizability	47.83 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

NPA025691

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

146682170

PDB ID

Not Available

ChEBI ID

156391

Good Scents ID

Not Available

References

General References

Showing NP-Card for Perquinoline A (NP0020083)

MOL for NP0020083 (Perquinoline A)

3D MOL for NP0020083 (Perquinoline A)

3D SDF for NP0020083 (Perquinoline A)

3D-SDF for NP0020083 (Perquinoline A)

PDB for NP0020083 (Perquinoline A)

3D PDB for NP0020083 (Perquinoline A)

SMILES for NP0020083 (Perquinoline A)

INCHI for NP0020083 (Perquinoline A)

Structure for NP0020083 (Perquinoline A)

3D Structure for NP0020083 (Perquinoline A)