NP-MRD: Showing NP-Card for CI-4 (NP0023081)

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Record Information

Version

2.0

Created at

2021-01-06 08:12:24 UTC

Updated at

2021-07-15 17:40:46 UTC

NP-MRD ID

NP0023081

Secondary Accession Numbers

None

Natural Product Identification

Common Name

CI-4

Provided By

NPAtlas

Description

CI-4 is found in Axinella vaceleti, Pseudomonas, Pseudomonas sp. IZ208 and Streptomyces nigra. CI-4 was first documented in 1996 (PMID: 8609091). Based on a literature review very few articles have been published on Verpacamide A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105393D          

 37 38  0  0  0  0            999 V2000
    5.6534   -0.9206   -0.3732 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3484    0.4570   -0.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3181    1.4594   -0.4513 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1661    0.8256    0.1008 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1651   -0.1923    0.3270 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8440    0.3810   -0.1780 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7669   -0.6343    0.0320 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5501   -0.1053   -0.4537 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9483    1.1080    0.2434 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3021    1.5386    0.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6515    2.6455    0.7240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3219    0.6571   -0.3303 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6715    0.7796    0.3585 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3014   -0.5632   -0.0328 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1502   -1.5049    0.2535 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9820   -0.7496   -0.1285 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6260   -1.1237   -0.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3318   -2.3635   -0.4089 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1726   -1.5350   -1.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3902   -1.3983    0.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7866    1.5597   -1.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5623    2.1028    0.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0485   -0.4407    1.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3438   -1.1110   -0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6927    1.3247    0.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9205    0.5622   -1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0166   -1.5310   -0.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6954   -0.9274    1.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4320    0.1253   -1.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2722    1.7136    0.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4364    0.8934   -1.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2610    1.6231   -0.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5534    0.7816    1.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4667   -0.5115   -1.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1985   -0.7857    0.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1794   -1.6868    1.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2548   -2.4532   -0.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  3  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17  8  1  0  0  0  0
 16 12  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  3 21  1  0  0  0  0
  3 22  1  0  0  0  0
  5 23  1  0  0  0  0
  5 24  1  0  0  0  0
  6 25  1  0  0  0  0
  6 26  1  0  0  0  0
  7 27  1  0  0  0  0
  7 28  1  0  0  0  0
  8 29  1  6  0  0  0
  9 30  1  0  0  0  0
 12 31  1  6  0  0  0
 13 32  1  0  0  0  0
 13 33  1  0  0  0  0
 14 34  1  0  0  0  0
 14 35  1  0  0  0  0
 15 36  1  0  0  0  0
 15 37  1  0  0  0  0
M  END

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
    5.6534   -0.9206   -0.3732 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3484    0.4570   -0.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3181    1.4594   -0.4513 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1661    0.8256    0.1008 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1651   -0.1923    0.3270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8440    0.3810   -0.1780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7669   -0.6343    0.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5501   -0.1053   -0.4537 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9483    1.1080    0.2434 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3021    1.5386    0.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6515    2.6455    0.7240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3219    0.6571   -0.3303 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6715    0.7796    0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3014   -0.5632   -0.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1502   -1.5049    0.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9820   -0.7496   -0.1285 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6260   -1.1237   -0.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3318   -2.3635   -0.4089 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1726   -1.5350   -1.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3902   -1.3983    0.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7866    1.5597   -1.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5623    2.1028    0.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0485   -0.4407    1.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3438   -1.1110   -0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6927    1.3247    0.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9205    0.5622   -1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0166   -1.5310   -0.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6954   -0.9274    1.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4320    0.1253   -1.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2722    1.7136    0.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4364    0.8934   -1.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2610    1.6231   -0.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5534    0.7816    1.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4667   -0.5115   -1.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1985   -0.7857    0.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1794   -1.6868    1.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2548   -2.4532   -0.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17  8  1  0
 16 12  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  6
  9 30  1  0
 12 31  1  6
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
M  END


  Mrv1652306242105393D          

 37 38  0  0  0  0            999 V2000
    5.6534   -0.9206   -0.3732 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3484    0.4570   -0.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3181    1.4594   -0.4513 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1661    0.8256    0.1008 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1651   -0.1923    0.3270 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8440    0.3810   -0.1780 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7669   -0.6343    0.0320 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5501   -0.1053   -0.4537 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9483    1.1080    0.2434 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3021    1.5386    0.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6515    2.6455    0.7240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3219    0.6571   -0.3303 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6715    0.7796    0.3585 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3014   -0.5632   -0.0328 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1502   -1.5049    0.2535 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9820   -0.7496   -0.1285 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6260   -1.1237   -0.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3318   -2.3635   -0.4089 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1726   -1.5350   -1.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3902   -1.3983    0.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7866    1.5597   -1.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5623    2.1028    0.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0485   -0.4407    1.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3438   -1.1110   -0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6927    1.3247    0.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9205    0.5622   -1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0166   -1.5310   -0.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6954   -0.9274    1.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4320    0.1253   -1.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2722    1.7136    0.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4364    0.8934   -1.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2610    1.6231   -0.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5534    0.7816    1.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4667   -0.5115   -1.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1985   -0.7857    0.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1794   -1.6868    1.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2548   -2.4532   -0.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  3  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17  8  1  0  0  0  0
 16 12  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  3 21  1  0  0  0  0
  3 22  1  0  0  0  0
  5 23  1  0  0  0  0
  5 24  1  0  0  0  0
  6 25  1  0  0  0  0
  6 26  1  0  0  0  0
  7 27  1  0  0  0  0
  7 28  1  0  0  0  0
  8 29  1  6  0  0  0
  9 30  1  0  0  0  0
 12 31  1  6  0  0  0
 13 32  1  0  0  0  0
 13 33  1  0  0  0  0
 14 34  1  0  0  0  0
 14 35  1  0  0  0  0
 15 36  1  0  0  0  0
 15 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0023081

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H19N5O2/c12-11(13)14-5-1-3-7-10(18)16-6-2-4-8(16)9(17)15-7/h7-8H,1-6H2,(H,15,17)(H4,12,13,14)/t7-,8-/m0/s1

> <INCHI_KEY>
ZRJHYOXNWCMGMW-YUMQZZPRSA-N

> <FORMULA>
C11H19N5O2

> <MOLECULAR_WEIGHT>
253.3009

> <EXACT_MASS>
253.153874877

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
27.35134245532217

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N''-{3-[(3S,8aS)-1,4-dioxo-octahydropyrrolo[1,2-a]pyrazin-3-yl]propyl}guanidine

> <ALOGPS_LOGP>
-1.52

> <JCHEM_LOGP>
-2.1277527501681073

> <ALOGPS_LOGS>
-1.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.50364969516612

> <JCHEM_PKA_STRONGEST_BASIC>
10.866131462233481

> <JCHEM_POLAR_SURFACE_AREA>
113.81

> <JCHEM_REFRACTIVITY>
65.41690000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.93e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N''-{3-[(3S,8aS)-1,4-dioxo-hexahydropyrrolo[1,2-a]pyrazin-3-yl]propyl}guanidine

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
    5.6534   -0.9206   -0.3732 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3484    0.4570   -0.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3181    1.4594   -0.4513 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1661    0.8256    0.1008 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1651   -0.1923    0.3270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8440    0.3810   -0.1780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7669   -0.6343    0.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5501   -0.1053   -0.4537 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9483    1.1080    0.2434 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3021    1.5386    0.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6515    2.6455    0.7240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3219    0.6571   -0.3303 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6715    0.7796    0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3014   -0.5632   -0.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1502   -1.5049    0.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9820   -0.7496   -0.1285 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6260   -1.1237   -0.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3318   -2.3635   -0.4089 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1726   -1.5350   -1.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3902   -1.3983    0.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7866    1.5597   -1.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5623    2.1028    0.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0485   -0.4407    1.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3438   -1.1110   -0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6927    1.3247    0.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9205    0.5622   -1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0166   -1.5310   -0.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6954   -0.9274    1.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4320    0.1253   -1.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2722    1.7136    0.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4364    0.8934   -1.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2610    1.6231   -0.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5534    0.7816    1.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4667   -0.5115   -1.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1985   -0.7857    0.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1794   -1.6868    1.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2548   -2.4532   -0.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17  8  1  0
 16 12  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  6
  9 30  1  0
 12 31  1  6
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  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       5.653  -0.921  -0.373  0.00  0.00           N+0
HETATM    2  C   UNK     0       5.348   0.457  -0.233  0.00  0.00           C+0
HETATM    3  N   UNK     0       6.318   1.459  -0.451  0.00  0.00           N+0
HETATM    4  N   UNK     0       4.166   0.826   0.101  0.00  0.00           N+0
HETATM    5  C   UNK     0       3.165  -0.192   0.327  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.844   0.381  -0.178  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.767  -0.634   0.032  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.550  -0.105  -0.454  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.948   1.108   0.243  0.00  0.00           N+0
HETATM   10  C   UNK     0      -2.302   1.539   0.246  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.652   2.646   0.724  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.322   0.657  -0.330  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.672   0.780   0.359  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.301  -0.563  -0.033  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.150  -1.505   0.254  0.00  0.00           C+0
HETATM   16  N   UNK     0      -2.982  -0.750  -0.129  0.00  0.00           N+0
HETATM   17  C   UNK     0      -1.626  -1.124  -0.331  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.332  -2.364  -0.409  0.00  0.00           O+0
HETATM   19  H   UNK     0       5.173  -1.535  -1.066  0.00  0.00           H+0
HETATM   20  H   UNK     0       6.390  -1.398   0.223  0.00  0.00           H+0
HETATM   21  H   UNK     0       6.787   1.560  -1.365  0.00  0.00           H+0
HETATM   22  H   UNK     0       6.562   2.103   0.316  0.00  0.00           H+0
HETATM   23  H   UNK     0       3.049  -0.441   1.401  0.00  0.00           H+0
HETATM   24  H   UNK     0       3.344  -1.111  -0.266  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.693   1.325   0.384  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.921   0.562  -1.277  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.017  -1.531  -0.538  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.695  -0.927   1.100  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.432   0.125  -1.539  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.272   1.714   0.768  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.436   0.893  -1.417  0.00  0.00           H+0
HETATM   32  H   UNK     0      -5.261   1.623  -0.040  0.00  0.00           H+0
HETATM   33  H   UNK     0      -4.553   0.782   1.446  0.00  0.00           H+0
HETATM   34  H   UNK     0      -5.467  -0.511  -1.130  0.00  0.00           H+0
HETATM   35  H   UNK     0      -6.199  -0.786   0.544  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.179  -1.687   1.364  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.255  -2.453  -0.313  0.00  0.00           H+0
CONECT    1    2   19   20                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2   21   22                                                  
CONECT    4    2    5                                                       
CONECT    5    4    6   23   24                                             
CONECT    6    5    7   25   26                                             
CONECT    7    6    8   27   28                                             
CONECT    8    7    9   17   29                                             
CONECT    9    8   10   30                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   16   31                                             
CONECT   13   12   14   32   33                                             
CONECT   14   13   15   34   35                                             
CONECT   15   14   16   36   37                                             
CONECT   16   15   17   12                                                  
CONECT   17   16   18    8                                                  
CONECT   18   17                                                            
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    3                                                            
CONECT   22    3                                                            
CONECT   23    5                                                            
CONECT   24    5                                                            
CONECT   25    6                                                            
CONECT   26    6                                                            
CONECT   27    7                                                            
CONECT   28    7                                                            
CONECT   29    8                                                            
CONECT   30    9                                                            
CONECT   31   12                                                            
CONECT   32   13                                                            
CONECT   33   13                                                            
CONECT   34   14                                                            
CONECT   35   14                                                            
CONECT   36   15                                                            
CONECT   37   15                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   76    0
END

RDKit          3D

37 38  0  0  0  0  0  0  0  0999 V2000
    5.6534   -0.9206   -0.3732 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3484    0.4570   -0.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3181    1.4594   -0.4513 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1661    0.8256    0.1008 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1651   -0.1923    0.3270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8440    0.3810   -0.1780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7669   -0.6343    0.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5501   -0.1053   -0.4537 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9483    1.1080    0.2434 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3021    1.5386    0.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6515    2.6455    0.7240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3219    0.6571   -0.3303 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6715    0.7796    0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3014   -0.5632   -0.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1502   -1.5049    0.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9820   -0.7496   -0.1285 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6260   -1.1237   -0.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3318   -2.3635   -0.4089 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1726   -1.5350   -1.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3902   -1.3983    0.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7866    1.5597   -1.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5623    2.1028    0.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0485   -0.4407    1.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3438   -1.1110   -0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6927    1.3247    0.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9205    0.5622   -1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0166   -1.5310   -0.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6954   -0.9274    1.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4320    0.1253   -1.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2722    1.7136    0.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4364    0.8934   -1.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2610    1.6231   -0.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5534    0.7816    1.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4667   -0.5115   -1.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1985   -0.7857    0.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1794   -1.6868    1.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2548   -2.4532   -0.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17  8  1  0
 16 12  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  6
  9 30  1  0
 12 31  1  6
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
CI 4	MeSH
Cyclo(arg-pro)	MeSH
CI-4	MeSH
Cyclo(L-arg-D-pro)	MeSH
Cyclo(arginyl-prolyl)	MeSH

Chemical Formula

C₁₁H₁₉N₅O₂

Average Mass

253.3009 Da

Monoisotopic Mass

253.15387 Da

IUPAC Name

N''-{3-[(3S,8aS)-1,4-dioxo-octahydropyrrolo[1,2-a]pyrazin-3-yl]propyl}guanidine

Traditional Name

N''-{3-[(3S,8aS)-1,4-dioxo-hexahydropyrrolo[1,2-a]pyrazin-3-yl]propyl}guanidine

CAS Registry Number

Not Available

SMILES

NC(N)=NCCC[C@@H]1NC(=O)[C@@H]2CCCN2C1=O

InChI Identifier

InChI=1S/C11H19N5O2/c12-11(13)14-5-1-3-7-10(18)16-6-2-4-8(16)9(17)15-7/h7-8H,1-6H2,(H,15,17)(H4,12,13,14)/t7-,8-/m0/s1

InChI Key

ZRJHYOXNWCMGMW-YUMQZZPRSA-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
Axinella vaceleti	LOTUS Database	35616633
Pseudomonas	NPAtlas	8609091
Pseudomonas sp. IZ208	Bacteria	KNApSAcK
Streptomyces nigra	LOTUS Database	35616633

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Dioxopiperazine
2,5-dioxopiperazine
N-alkylpiperazine
1,4-diazinane
Piperazine
Pyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Guanidine
Lactam
Secondary carboxylic acid amide
Azacycle
Carboximidamide
Organoheterocyclic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

guanidines (CHEBI:40745 )
pyrrolopyrazine (CHEBI:40745 )

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	-1.5	ALOGPS
logP	-2.1	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	11.5	ChemAxon
pKa (Strongest Basic)	10.87	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.81 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	65.42 m³·mol⁻¹	ChemAxon
Polarizability	27.35 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA002778

HMDB ID

Not Available

DrugBank ID

DB04433

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

395718

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

449095

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Izumida H, Imamura N, Sano H: A novel chitinase inhibitor from a marine bacterium, Pseudomonas sp. J Antibiot (Tokyo). 1996 Jan;49(1):76-80. doi: 10.7164/antibiotics.49.76. [PubMed:8609091 ]

Showing NP-Card for CI-4 (NP0023081)

MOL for NP0023081 (CI-4)

3D MOL for NP0023081 (CI-4)

3D SDF for NP0023081 (CI-4)

3D-SDF for NP0023081 (CI-4)

PDB for NP0023081 (CI-4)

3D PDB for NP0023081 (CI-4)

SMILES for NP0023081 (CI-4)

INCHI for NP0023081 (CI-4)

Structure for NP0023081 (CI-4)

3D Structure for NP0023081 (CI-4)