NP-MRD: Showing NP-Card for Distomadine A (NP0026225)

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Record Information

Version

2.0

Created at

2021-06-19 18:08:43 UTC

Updated at

2021-06-29 23:51:38 UTC

NP-MRD ID

NP0026225

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Distomadine A

Provided By

JEOL Database JEOL Logo

Description

Distomadine A is found in Pseudodistoma aureum. Distomadine A was first documented in 2003 (Pearce, A. N., et al.). Based on a literature review very few articles have been published on 3,4-[Oxy(6-hydroxyquinoline-4,5-diyl)]-5alpha-(2-guanidinoethyl)-2,5-dihydrofuran-2-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120083D          

 38 41  0  0  0  0            999 V2000
    2.1627    0.0865   -2.7590 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0785   -1.0555   -3.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7807   -1.3379   -4.4563 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2947   -2.0780   -2.9477 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4627   -2.0583   -1.7593 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8096   -1.2497   -2.0124 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4868   -0.8582   -0.6918 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6520   -1.6958   -0.5169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7865   -0.9283   -0.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9245   -1.3535   -0.4607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3870    0.4747   -0.6531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0586    0.5021   -0.7120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3831    1.7904   -0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0016    1.9730   -0.8266 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8393    0.9195   -0.6280 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5396    3.2409   -0.9885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3130    4.3430   -1.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6965    4.2083   -1.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4866    5.2921   -1.1985 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8292    5.1180   -1.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4468    3.8940   -0.9843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6269    2.7836   -0.8742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2272    2.9170   -0.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2378    1.5509   -0.7064 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8342    0.6523   -3.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7464   -2.2511   -4.8823 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4088   -0.6675   -4.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2396   -2.9135   -3.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1920   -3.0869   -1.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0425   -1.6649   -0.9176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4852   -1.8451   -2.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5637   -0.3585   -2.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8444   -1.0032    0.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3797    0.7830   -1.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6163    3.3842   -0.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1126    5.3369   -1.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4136    6.0296   -1.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5258    3.8086   -0.9456 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0  0  0  0
 11 24  1  0  0  0  0
 11 12  2  0  0  0  0
 21 22  2  0  0  0  0
 20 19  2  0  0  0  0
 18 17  1  0  0  0  0
 17 16  2  0  0  0  0
 16 14  1  0  0  0  0
 12  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 11  1  0  0  0  0
 14 13  2  0  0  0  0
  9 10  2  0  0  0  0
 22 23  1  0  0  0  0
  7  6  1  0  0  0  0
 19 18  1  0  0  0  0
  6  5  1  0  0  0  0
 23 18  2  0  0  0  0
  5  4  1  0  0  0  0
 21 20  1  0  0  0  0
  4  2  1  0  0  0  0
  2  3  1  0  0  0  0
 22 24  1  0  0  0  0
  2  1  2  3  0  0  0
 23 13  1  0  0  0  0
 14 15  1  0  0  0  0
 21 38  1  0  0  0  0
 20 37  1  0  0  0  0
 17 36  1  0  0  0  0
 16 35  1  0  0  0  0
  7 33  1  1  0  0  0
  6 31  1  0  0  0  0
  6 32  1  0  0  0  0
  5 29  1  0  0  0  0
  5 30  1  0  0  0  0
  4 28  1  0  0  0  0
  3 26  1  0  0  0  0
  3 27  1  0  0  0  0
  1 25  1  0  0  0  0
 15 34  1  0  0  0  0
M  END

     RDKit          3D

 38 41  0  0  0  0  0  0  0  0999 V2000
    2.1627    0.0865   -2.7590 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0785   -1.0555   -3.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7807   -1.3379   -4.4563 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2947   -2.0780   -2.9477 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4627   -2.0583   -1.7593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8096   -1.2497   -2.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4868   -0.8582   -0.6918 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6520   -1.6958   -0.5169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7865   -0.9283   -0.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9245   -1.3535   -0.4607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3870    0.4747   -0.6531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0586    0.5021   -0.7120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3831    1.7904   -0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0016    1.9730   -0.8266 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8393    0.9195   -0.6280 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5396    3.2409   -0.9885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3130    4.3430   -1.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6965    4.2083   -1.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4866    5.2921   -1.1985 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8292    5.1180   -1.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4468    3.8940   -0.9843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6269    2.7836   -0.8742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2272    2.9170   -0.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2378    1.5509   -0.7064 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8342    0.6523   -3.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7464   -2.2511   -4.8823 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4088   -0.6675   -4.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2396   -2.9135   -3.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1920   -3.0869   -1.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0425   -1.6649   -0.9176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4852   -1.8451   -2.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5637   -0.3585   -2.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8444   -1.0032    0.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3797    0.7830   -1.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6163    3.3842   -0.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1126    5.3369   -1.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4136    6.0296   -1.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5258    3.8086   -0.9456 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 11 24  1  0
 11 12  2  0
 21 22  2  0
 20 19  2  0
 18 17  1  0
 17 16  2  0
 16 14  1  0
 12  7  1  0
  7  8  1  0
  8  9  1  0
  9 11  1  0
 14 13  2  0
  9 10  2  0
 22 23  1  0
  7  6  1  0
 19 18  1  0
  6  5  1  0
 23 18  2  0
  5  4  1  0
 21 20  1  0
  4  2  1  0
  2  3  1  0
 22 24  1  0
  2  1  2  3
 23 13  1  0
 14 15  1  0
 21 38  1  0
 20 37  1  0
 17 36  1  0
 16 35  1  0
  7 33  1  1
  6 31  1  0
  6 32  1  0
  5 29  1  0
  5 30  1  0
  4 28  1  0
  3 26  1  0
  3 27  1  0
  1 25  1  0
 15 34  1  0
M  END


  Mrv1652306192120083D          

 38 41  0  0  0  0            999 V2000
    2.1627    0.0865   -2.7590 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0785   -1.0555   -3.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7807   -1.3379   -4.4563 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2947   -2.0780   -2.9477 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4627   -2.0583   -1.7593 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8096   -1.2497   -2.0124 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4868   -0.8582   -0.6918 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6520   -1.6958   -0.5169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7865   -0.9283   -0.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9245   -1.3535   -0.4607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3870    0.4747   -0.6531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0586    0.5021   -0.7120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3831    1.7904   -0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0016    1.9730   -0.8266 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8393    0.9195   -0.6280 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5396    3.2409   -0.9885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3130    4.3430   -1.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6965    4.2083   -1.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4866    5.2921   -1.1985 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8292    5.1180   -1.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4468    3.8940   -0.9843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6269    2.7836   -0.8742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2272    2.9170   -0.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2378    1.5509   -0.7064 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8342    0.6523   -3.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7464   -2.2511   -4.8823 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4088   -0.6675   -4.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2396   -2.9135   -3.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1920   -3.0869   -1.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0425   -1.6649   -0.9176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4852   -1.8451   -2.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5637   -0.3585   -2.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8444   -1.0032    0.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3797    0.7830   -1.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6163    3.3842   -0.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1126    5.3369   -1.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4136    6.0296   -1.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5258    3.8086   -0.9456 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0  0  0  0
 11 24  1  0  0  0  0
 11 12  2  0  0  0  0
 21 22  2  0  0  0  0
 20 19  2  0  0  0  0
 18 17  1  0  0  0  0
 17 16  2  0  0  0  0
 16 14  1  0  0  0  0
 12  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 11  1  0  0  0  0
 14 13  2  0  0  0  0
  9 10  2  0  0  0  0
 22 23  1  0  0  0  0
  7  6  1  0  0  0  0
 19 18  1  0  0  0  0
  6  5  1  0  0  0  0
 23 18  2  0  0  0  0
  5  4  1  0  0  0  0
 21 20  1  0  0  0  0
  4  2  1  0  0  0  0
  2  3  1  0  0  0  0
 22 24  1  0  0  0  0
  2  1  2  3  0  0  0
 23 13  1  0  0  0  0
 14 15  1  0  0  0  0
 21 38  1  0  0  0  0
 20 37  1  0  0  0  0
 17 36  1  0  0  0  0
 16 35  1  0  0  0  0
  7 33  1  1  0  0  0
  6 31  1  0  0  0  0
  6 32  1  0  0  0  0
  5 29  1  0  0  0  0
  5 30  1  0  0  0  0
  4 28  1  0  0  0  0
  3 26  1  0  0  0  0
  3 27  1  0  0  0  0
  1 25  1  0  0  0  0
 15 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0026225

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C3=C(OC4=C([H])C([H])=NC(C([H])=C1[H])=C24)C(=O)O[C@@]3([H])C([H])([H])C([H])([H])N([H])C(=N[H])N([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H14N4O4/c17-16(18)20-6-4-10-13-12-8(21)2-1-7-11(12)9(3-5-19-7)23-14(13)15(22)24-10/h1-3,5,10,21H,4,6H2,(H4,17,18,20)/t10-/m0/s1

> <INCHI_KEY>
YTJQNXMCZWEMBC-JTQLQIEISA-N

> <FORMULA>
C16H14N4O4

> <MOLECULAR_WEIGHT>
326.312

> <EXACT_MASS>
326.101504947

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
32.332134504302644

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-{2-[(11S)-8-hydroxy-13-oxo-12,15-dioxa-4-azatetracyclo[7.6.1.0^{5,16}.0^{10,14}]hexadeca-1,3,5(16),6,8,10(14)-hexaen-11-yl]ethyl}guanidine

> <ALOGPS_LOGP>
0.98

> <JCHEM_LOGP>
-0.0885664072253937

> <ALOGPS_LOGS>
-3.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.94154165598642

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.437576924402

> <JCHEM_PKA_STRONGEST_BASIC>
11.9872016636057

> <JCHEM_POLAR_SURFACE_AREA>
130.55

> <JCHEM_REFRACTIVITY>
94.8959

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.76e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-{2-[(11S)-8-hydroxy-13-oxo-12,15-dioxa-4-azatetracyclo[7.6.1.0^{5,16}.0^{10,14}]hexadeca-1,3,5(16),6,8,10(14)-hexaen-11-yl]ethyl}guanidine

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 38 41  0  0  0  0  0  0  0  0999 V2000
    2.1627    0.0865   -2.7590 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0785   -1.0555   -3.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7807   -1.3379   -4.4563 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2947   -2.0780   -2.9477 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4627   -2.0583   -1.7593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8096   -1.2497   -2.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4868   -0.8582   -0.6918 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6520   -1.6958   -0.5169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7865   -0.9283   -0.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9245   -1.3535   -0.4607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3870    0.4747   -0.6531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0586    0.5021   -0.7120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3831    1.7904   -0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0016    1.9730   -0.8266 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8393    0.9195   -0.6280 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5396    3.2409   -0.9885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3130    4.3430   -1.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6965    4.2083   -1.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4866    5.2921   -1.1985 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8292    5.1180   -1.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4468    3.8940   -0.9843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6269    2.7836   -0.8742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2272    2.9170   -0.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2378    1.5509   -0.7064 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8342    0.6523   -3.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7464   -2.2511   -4.8823 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4088   -0.6675   -4.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2396   -2.9135   -3.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1920   -3.0869   -1.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0425   -1.6649   -0.9176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4852   -1.8451   -2.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5637   -0.3585   -2.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8444   -1.0032    0.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3797    0.7830   -1.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6163    3.3842   -0.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1126    5.3369   -1.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4136    6.0296   -1.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5258    3.8086   -0.9456 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 11 24  1  0
 11 12  2  0
 21 22  2  0
 20 19  2  0
 18 17  1  0
 17 16  2  0
 16 14  1  0
 12  7  1  0
  7  8  1  0
  8  9  1  0
  9 11  1  0
 14 13  2  0
  9 10  2  0
 22 23  1  0
  7  6  1  0
 19 18  1  0
  6  5  1  0
 23 18  2  0
  5  4  1  0
 21 20  1  0
  4  2  1  0
  2  3  1  0
 22 24  1  0
  2  1  2  3
 23 13  1  0
 14 15  1  0
 21 38  1  0
 20 37  1  0
 17 36  1  0
 16 35  1  0
  7 33  1  1
  6 31  1  0
  6 32  1  0
  5 29  1  0
  5 30  1  0
  4 28  1  0
  3 26  1  0
  3 27  1  0
  1 25  1  0
 15 34  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  N   UNK     0       2.163   0.087  -2.759  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.079  -1.056  -3.350  0.00  0.00           C+0
HETATM    3  N   UNK     0       2.781  -1.338  -4.456  0.00  0.00           N+0
HETATM    4  N   UNK     0       1.295  -2.078  -2.948  0.00  0.00           N+0
HETATM    5  C   UNK     0       0.463  -2.058  -1.759  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.810  -1.250  -2.012  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.487  -0.858  -0.692  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.652  -1.696  -0.517  0.00  0.00           O+0
HETATM    9  C   UNK     0      -3.787  -0.928  -0.535  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.925  -1.353  -0.461  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.387   0.475  -0.653  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.059   0.502  -0.712  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.383   1.790  -0.813  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.002   1.973  -0.827  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.839   0.920  -0.628  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.540   3.241  -0.989  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.313   4.343  -1.122  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.696   4.208  -1.085  0.00  0.00           C+0
HETATM   19  N   UNK     0      -2.487   5.292  -1.198  0.00  0.00           N+0
HETATM   20  C   UNK     0      -3.829   5.118  -1.146  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.447   3.894  -0.984  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.627   2.784  -0.874  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.227   2.917  -0.925  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.238   1.551  -0.706  0.00  0.00           O+0
HETATM   25  H   UNK     0       2.834   0.652  -3.289  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.746  -2.251  -4.882  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.409  -0.668  -4.874  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.240  -2.914  -3.511  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.192  -3.087  -1.495  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.042  -1.665  -0.918  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.485  -1.845  -2.641  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.564  -0.359  -2.601  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.844  -1.003   0.183  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.380   0.783  -1.450  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.616   3.384  -0.989  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.113   5.337  -1.241  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.414   6.030  -1.240  0.00  0.00           H+0
HETATM   38  H   UNK     0      -5.526   3.809  -0.946  0.00  0.00           H+0
CONECT    1    2   25                                                       
CONECT    2    4    3    1                                                  
CONECT    3    2   26   27                                                  
CONECT    4    5    2   28                                                  
CONECT    5    6    4   29   30                                             
CONECT    6    7    5   31   32                                             
CONECT    7   12    8    6   33                                             
CONECT    8    7    9                                                       
CONECT    9    8   11   10                                                  
CONECT   10    9                                                            
CONECT   11   24   12    9                                                  
CONECT   12   13   11    7                                                  
CONECT   13   12   14   23                                                  
CONECT   14   16   13   15                                                  
CONECT   15   14   34                                                       
CONECT   16   17   14   35                                                  
CONECT   17   18   16   36                                                  
CONECT   18   17   19   23                                                  
CONECT   19   20   18                                                       
CONECT   20   19   21   37                                                  
CONECT   21   22   20   38                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22   18   13                                                  
CONECT   24   11   22                                                       
CONECT   25    1                                                            
CONECT   26    3                                                            
CONECT   27    3                                                            
CONECT   28    4                                                            
CONECT   29    5                                                            
CONECT   30    5                                                            
CONECT   31    6                                                            
CONECT   32    6                                                            
CONECT   33    7                                                            
CONECT   34   15                                                            
CONECT   35   16                                                            
CONECT   36   17                                                            
CONECT   37   20                                                            
CONECT   38   21                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

RDKit          3D

38 41  0  0  0  0  0  0  0  0999 V2000
    2.1627    0.0865   -2.7590 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0785   -1.0555   -3.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7807   -1.3379   -4.4563 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2947   -2.0780   -2.9477 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4627   -2.0583   -1.7593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8096   -1.2497   -2.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4868   -0.8582   -0.6918 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6520   -1.6958   -0.5169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7865   -0.9283   -0.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9245   -1.3535   -0.4607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3870    0.4747   -0.6531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0586    0.5021   -0.7120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3831    1.7904   -0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0016    1.9730   -0.8266 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8393    0.9195   -0.6280 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5396    3.2409   -0.9885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3130    4.3430   -1.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6965    4.2083   -1.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4866    5.2921   -1.1985 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8292    5.1180   -1.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4468    3.8940   -0.9843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6269    2.7836   -0.8742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2272    2.9170   -0.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2378    1.5509   -0.7064 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8342    0.6523   -3.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7464   -2.2511   -4.8823 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4088   -0.6675   -4.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2396   -2.9135   -3.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1920   -3.0869   -1.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0425   -1.6649   -0.9176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4852   -1.8451   -2.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5637   -0.3585   -2.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8444   -1.0032    0.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3797    0.7830   -1.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6163    3.3842   -0.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1126    5.3369   -1.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4136    6.0296   -1.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5258    3.8086   -0.9456 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 11 24  1  0
 11 12  2  0
 21 22  2  0
 20 19  2  0
 18 17  1  0
 17 16  2  0
 16 14  1  0
 12  7  1  0
  7  8  1  0
  8  9  1  0
  9 11  1  0
 14 13  2  0
  9 10  2  0
 22 23  1  0
  7  6  1  0
 19 18  1  0
  6  5  1  0
 23 18  2  0
  5  4  1  0
 21 20  1  0
  4  2  1  0
  2  3  1  0
 22 24  1  0
  2  1  2  3
 23 13  1  0
 14 15  1  0
 21 38  1  0
 20 37  1  0
 17 36  1  0
 16 35  1  0
  7 33  1  1
  6 31  1  0
  6 32  1  0
  5 29  1  0
  5 30  1  0
  4 28  1  0
  3 26  1  0
  3 27  1  0
  1 25  1  0
 15 34  1  0
M  END

View in JSmol

Synonyms

Value	Source
3,4-[Oxy(6-hydroxyquinoline-4,5-diyl)]-5a-(2-guanidinoethyl)-2,5-dihydrofuran-2-one	Generator
3,4-[Oxy(6-hydroxyquinoline-4,5-diyl)]-5α-(2-guanidinoethyl)-2,5-dihydrofuran-2-one	Generator

Chemical Formula

C₁₆H₁₄N₄O₄

Average Mass

326.3120 Da

Monoisotopic Mass

326.10150 Da

IUPAC Name

N-{2-[(11S)-8-hydroxy-13-oxo-12,15-dioxa-4-azatetracyclo[7.6.1.0^{5,16}.0^{10,14}]hexadeca-1,3,5(16),6,8,10(14)-hexaen-11-yl]ethyl}guanidine

Traditional Name

N-{2-[(11S)-8-hydroxy-13-oxo-12,15-dioxa-4-azatetracyclo[7.6.1.0^{5,16}.0^{10,14}]hexadeca-1,3,5(16),6,8,10(14)-hexaen-11-yl]ethyl}guanidine

CAS Registry Number

Not Available

SMILES

[H]OC1=C2C3=C(OC4=C([H])C([H])=NC(C([H])=C1[H])=C24)C(=O)O[C@@]3([H])C([H])([H])C([H])([H])N([H])C(=N[H])N([H])[H]

InChI Identifier

InChI=1S/C16H14N4O4/c17-16(18)20-6-4-10-13-12-8(21)2-1-7-11(12)9(3-5-19-7)23-14(13)15(22)24-10/h1-3,5,10,21H,4,6H2,(H4,17,18,20)/t10-/m0/s1

InChI Key

YTJQNXMCZWEMBC-JTQLQIEISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pseudodistoma aureum	JEOL database	Pearce, A. N., et al, Tetrahedron Lett. 44, 3897 (2003)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyquinolines. Hydroxyquinolines are compounds containing a quinoline moiety bearing a hydroxyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Hydroxyquinolines

Direct Parent

Hydroxyquinolines

Alternative Parents

Substituents

Hydroxyquinoline
Benzopyran
Pyranopyridine
2-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyridine
Benzenoid
Heteroaromatic compound
Carboxylic acid ester
Guanidine
Lactone
Carboxylic acid derivative
Oxacycle
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	0.98	ALOGPS
logP	-0.089	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	8.44	ChemAxon
pKa (Strongest Basic)	11.99	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	130.55 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	94.9 m³·mol⁻¹	ChemAxon
Polarizability	32.33 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

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

102222288

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pearce, A. N., et al. (2003). Pearce, A. N., et al, Tetrahedron Lett. 44, 3897 (2003). Tetrahedron Lett.

Showing NP-Card for Distomadine A (NP0026225)

MOL for NP0026225 (Distomadine A)

3D MOL for NP0026225 (Distomadine A)

3D SDF for NP0026225 (Distomadine A)

3D-SDF for NP0026225 (Distomadine A)

PDB for NP0026225 (Distomadine A)

3D PDB for NP0026225 (Distomadine A)

SMILES for NP0026225 (Distomadine A)

INCHI for NP0026225 (Distomadine A)

Structure for NP0026225 (Distomadine A)

3D Structure for NP0026225 (Distomadine A)