NP-MRD: Showing NP-Card for (3R,8aR)-3-isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione (NP0331497)

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Record Information

Version

1.0

Created at

2023-02-08 04:01:53 UTC

Updated at

2024-05-12 01:15:22 UTC

NP-MRD ID

NP0331497

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3R,8aR)-3-isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione

Description

(3R,8aR)-1-hydroxy-3-(2-methylpropyl)-3H,4H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one 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. Based on a literature review very few articles have been published on (3R,8aR)-1-hydroxy-3-(2-methylpropyl)-3H,4H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118153D          

 33 34  0  0  0  0            999 V2000
   -3.5737   -0.0478    0.7378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6104   -0.0010   -0.4279 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1610    1.3953   -0.6800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5457   -1.0312   -0.3642 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6382   -1.0197    0.8044 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3036   -2.1150    0.6280 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6380   -1.9476    0.2525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3024   -2.9420   -0.1234 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2643   -0.6361    0.2922 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9719   -0.2269   -0.9674 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1766    1.2695   -0.7141 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0010    1.7084    0.1165 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3454    0.4581    0.5289 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470    0.2610    1.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4978    1.1588    1.7721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1889    0.8903    0.6643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0942   -0.0406    1.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2964   -0.8839    0.6047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2529   -0.3000   -1.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0819    1.5092   -0.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5236    2.0509    0.1536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6651    1.8375   -1.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -2.0335   -0.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0013   -1.0139   -1.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2283   -1.2677    1.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0578   -3.0737    0.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0478   -0.6400    1.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9304   -0.7627   -1.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3324   -0.3841   -1.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2446    1.8123   -1.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1496    1.3930   -0.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588    2.2742    0.9902 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3660    2.3490   -0.4989 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  1  0  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  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14  5  1  0  0  0  0
 13  9  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  2 19  1  6  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
  3 22  1  0  0  0  0
  4 23  1  0  0  0  0
  4 24  1  0  0  0  0
  5 25  1  1  0  0  0
  6 26  1  0  0  0  0
  9 27  1  1  0  0  0
 10 28  1  0  0  0  0
 10 29  1  0  0  0  0
 11 30  1  0  0  0  0
 11 31  1  0  0  0  0
 12 32  1  0  0  0  0
 12 33  1  0  0  0  0
M  END

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
   -3.5737   -0.0478    0.7378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6104   -0.0010   -0.4279 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1610    1.3953   -0.6800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5457   -1.0312   -0.3642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6382   -1.0197    0.8044 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3036   -2.1150    0.6280 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6380   -1.9476    0.2525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3024   -2.9420   -0.1234 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2643   -0.6361    0.2922 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9719   -0.2269   -0.9674 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1766    1.2695   -0.7141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0010    1.7084    0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3454    0.4581    0.5289 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470    0.2610    1.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4978    1.1588    1.7721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1889    0.8903    0.6643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0942   -0.0406    1.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2964   -0.8839    0.6047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2529   -0.3000   -1.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0819    1.5092   -0.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5236    2.0509    0.1536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6651    1.8375   -1.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -2.0335   -0.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0013   -1.0139   -1.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2283   -1.2677    1.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0578   -3.0737    0.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0478   -0.6400    1.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9304   -0.7627   -1.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3324   -0.3841   -1.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2446    1.8123   -1.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1496    1.3930   -0.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588    2.2742    0.9902 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3660    2.3490   -0.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14  5  1  0
 13  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  6
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  1
  6 26  1  0
  9 27  1  1
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
M  END


  Mrv1652306242118153D          

 33 34  0  0  0  0            999 V2000
   -3.5737   -0.0478    0.7378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6104   -0.0010   -0.4279 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1610    1.3953   -0.6800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5457   -1.0312   -0.3642 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6382   -1.0197    0.8044 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3036   -2.1150    0.6280 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6380   -1.9476    0.2525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3024   -2.9420   -0.1234 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2643   -0.6361    0.2922 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9719   -0.2269   -0.9674 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1766    1.2695   -0.7141 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0010    1.7084    0.1165 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3454    0.4581    0.5289 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470    0.2610    1.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4978    1.1588    1.7721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1889    0.8903    0.6643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0942   -0.0406    1.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2964   -0.8839    0.6047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2529   -0.3000   -1.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0819    1.5092   -0.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5236    2.0509    0.1536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6651    1.8375   -1.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -2.0335   -0.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0013   -1.0139   -1.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2283   -1.2677    1.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0578   -3.0737    0.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0478   -0.6400    1.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9304   -0.7627   -1.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3324   -0.3841   -1.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2446    1.8123   -1.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1496    1.3930   -0.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588    2.2742    0.9902 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3660    2.3490   -0.4989 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  1  0  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  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14  5  1  0  0  0  0
 13  9  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  2 19  1  6  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
  3 22  1  0  0  0  0
  4 23  1  0  0  0  0
  4 24  1  0  0  0  0
  5 25  1  1  0  0  0
  6 26  1  0  0  0  0
  9 27  1  1  0  0  0
 10 28  1  0  0  0  0
 10 29  1  0  0  0  0
 11 30  1  0  0  0  0
 11 31  1  0  0  0  0
 12 32  1  0  0  0  0
 12 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331497

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N1C(=O)[C@]2([H])N(C(=O)[C@@]1([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])C2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C11H18N2O2/c1-7(2)6-8-11(15)13-5-3-4-9(13)10(14)12-8/h7-9H,3-6H2,1-2H3,(H,12,14)/t8-,9-/m1/s1

> <INCHI_KEY>
SZJNCZMRZAUNQT-RKDXNWHRSA-N

> <FORMULA>
C11H18N2O2

> <MOLECULAR_WEIGHT>
210.277

> <EXACT_MASS>
210.136827828

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
22.657210815203133

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,8aR)-3-(2-methylpropyl)-octahydropyrrolo[1,2-a]pyrazine-1,4-dione

> <ALOGPS_LOGP>
0.21

> <JCHEM_LOGP>
0.4537377393333338

> <ALOGPS_LOGS>
-0.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.205506707721693

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.471552352464668

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3932305414786508

> <JCHEM_POLAR_SURFACE_AREA>
49.410000000000004

> <JCHEM_REFRACTIVITY>
55.95750000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.46e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,8aR)-3-(2-methylpropyl)-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
   -3.5737   -0.0478    0.7378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6104   -0.0010   -0.4279 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1610    1.3953   -0.6800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5457   -1.0312   -0.3642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6382   -1.0197    0.8044 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3036   -2.1150    0.6280 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6380   -1.9476    0.2525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3024   -2.9420   -0.1234 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2643   -0.6361    0.2922 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9719   -0.2269   -0.9674 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1766    1.2695   -0.7141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0010    1.7084    0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3454    0.4581    0.5289 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470    0.2610    1.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4978    1.1588    1.7721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1889    0.8903    0.6643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0942   -0.0406    1.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2964   -0.8839    0.6047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2529   -0.3000   -1.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0819    1.5092   -0.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5236    2.0509    0.1536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6651    1.8375   -1.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -2.0335   -0.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0013   -1.0139   -1.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2283   -1.2677    1.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0578   -3.0737    0.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0478   -0.6400    1.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9304   -0.7627   -1.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3324   -0.3841   -1.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2446    1.8123   -1.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1496    1.3930   -0.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588    2.2742    0.9902 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3660    2.3490   -0.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14  5  1  0
 13  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  6
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  1
  6 26  1  0
  9 27  1  1
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  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  C   UNK     0      -3.574  -0.048   0.738  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.610  -0.001  -0.428  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.161   1.395  -0.680  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.546  -1.031  -0.364  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.638  -1.020   0.804  0.00  0.00           C+0
HETATM    6  N   UNK     0       0.304  -2.115   0.628  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.638  -1.948   0.253  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.302  -2.942  -0.123  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.264  -0.636   0.292  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.972  -0.227  -0.967  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.177   1.270  -0.714  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.001   1.708   0.117  0.00  0.00           C+0
HETATM   13  N   UNK     0       1.345   0.458   0.529  0.00  0.00           N+0
HETATM   14  C   UNK     0       0.047   0.261   1.076  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.498   1.159   1.772  0.00  0.00           O+0
HETATM   16  H   UNK     0      -4.189   0.890   0.664  0.00  0.00           H+0
HETATM   17  H   UNK     0      -3.094  -0.041   1.713  0.00  0.00           H+0
HETATM   18  H   UNK     0      -4.296  -0.884   0.605  0.00  0.00           H+0
HETATM   19  H   UNK     0      -3.253  -0.300  -1.315  0.00  0.00           H+0
HETATM   20  H   UNK     0      -1.082   1.509  -0.885  0.00  0.00           H+0
HETATM   21  H   UNK     0      -2.524   2.051   0.154  0.00  0.00           H+0
HETATM   22  H   UNK     0      -2.665   1.837  -1.590  0.00  0.00           H+0
HETATM   23  H   UNK     0      -2.063  -2.034  -0.358  0.00  0.00           H+0
HETATM   24  H   UNK     0      -1.001  -1.014  -1.339  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.228  -1.268   1.714  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.058  -3.074   0.796  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.048  -0.640   1.105  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.930  -0.763  -1.023  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.332  -0.384  -1.861  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.245   1.812  -1.663  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.150   1.393  -0.169  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.359   2.274   0.990  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.366   2.349  -0.499  0.00  0.00           H+0
CONECT    1    2   16   17   18                                             
CONECT    2    1    3    4   19                                             
CONECT    3    2   20   21   22                                             
CONECT    4    2    5   23   24                                             
CONECT    5    4    6   14   25                                             
CONECT    6    5    7   26                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   13   27                                             
CONECT   10    9   11   28   29                                             
CONECT   11   10   12   30   31                                             
CONECT   12   11   13   32   33                                             
CONECT   13   12   14    9                                                  
CONECT   14   13   15    5                                                  
CONECT   15   14                                                            
CONECT   16    1                                                            
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    2                                                            
CONECT   20    3                                                            
CONECT   21    3                                                            
CONECT   22    3                                                            
CONECT   23    4                                                            
CONECT   24    4                                                            
CONECT   25    5                                                            
CONECT   26    6                                                            
CONECT   27    9                                                            
CONECT   28   10                                                            
CONECT   29   10                                                            
CONECT   30   11                                                            
CONECT   31   11                                                            
CONECT   32   12                                                            
CONECT   33   12                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

RDKit          3D

33 34  0  0  0  0  0  0  0  0999 V2000
   -3.5737   -0.0478    0.7378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6104   -0.0010   -0.4279 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1610    1.3953   -0.6800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5457   -1.0312   -0.3642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6382   -1.0197    0.8044 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3036   -2.1150    0.6280 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6380   -1.9476    0.2525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3024   -2.9420   -0.1234 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2643   -0.6361    0.2922 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9719   -0.2269   -0.9674 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1766    1.2695   -0.7141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0010    1.7084    0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3454    0.4581    0.5289 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470    0.2610    1.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4978    1.1588    1.7721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1889    0.8903    0.6643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0942   -0.0406    1.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2964   -0.8839    0.6047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2529   -0.3000   -1.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0819    1.5092   -0.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5236    2.0509    0.1536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6651    1.8375   -1.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -2.0335   -0.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0013   -1.0139   -1.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2283   -1.2677    1.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0578   -3.0737    0.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0478   -0.6400    1.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9304   -0.7627   -1.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3324   -0.3841   -1.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2446    1.8123   -1.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1496    1.3930   -0.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588    2.2742    0.9902 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3660    2.3490   -0.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14  5  1  0
 13  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  6
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  1
  6 26  1  0
  9 27  1  1
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₈N₂O₂

Average Mass

210.2770 Da

Monoisotopic Mass

210.13683 Da

IUPAC Name

(3R,8aR)-3-(2-methylpropyl)-octahydropyrrolo[1,2-a]pyrazine-1,4-dione

Traditional Name

(3R,8aR)-3-(2-methylpropyl)-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

CAS Registry Number

Not Available

SMILES

[H]N1C(=O)[C@]2([H])N(C(=O)[C@@]1([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])C2([H])[H]

InChI Identifier

InChI=1S/C11H18N2O2/c1-7(2)6-8-11(15)13-5-3-4-9(13)10(14)12-8/h7-9H,3-6H2,1-2H3,(H,12,14)/t8-,9-/m1/s1

InChI Key

SZJNCZMRZAUNQT-RKDXNWHRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, simulated)	Not Available	Not Available	Not Available	2024-05-11	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
fungicidicus SYH3		Not Available

Chemical Taxonomy

Description

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
Lactam
Secondary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.21	ALOGPS
logP	0.45	ChemAxon
logS	-0.67	ALOGPS
pKa (Strongest Acidic)	11.47	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.41 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	55.96 m³·mol⁻¹	ChemAxon
Polarizability	22.66 Å³	ChemAxon
Number of Rings	2	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

808691

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

927566

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu H, An M, Si H, Shan Y, Xu C, Hu G, Xie Y, Liu D, Li S, Qiu R, Zhang C, Wu Y: Identification of Cyclic Dipeptides and a New Compound (6-(5-Hydroxy-6-methylheptyl)-5,6-dihydro-2H-pyran-2-one) Produced by Streptomyces fungicidicus against Alternaria solani. Molecules. 2022 Sep 1;27(17):5649. doi: 10.3390/molecules27175649. [PubMed:36080412 ]

Showing NP-Card for (3R,8aR)-3-isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione (NP0331497)

MOL for NP0331497 ((3R,8aR)-3-isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione)

3D MOL for NP0331497 ((3R,8aR)-3-isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione)

3D SDF for NP0331497 ((3R,8aR)-3-isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione)

3D-SDF for NP0331497 ((3R,8aR)-3-isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione)

PDB for NP0331497 ((3R,8aR)-3-isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione)

3D PDB for NP0331497 ((3R,8aR)-3-isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione)

SMILES for NP0331497 ((3R,8aR)-3-isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione)

INCHI for NP0331497 ((3R,8aR)-3-isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione)

Structure for NP0331497 ((3R,8aR)-3-isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione)

3D Structure for NP0331497 ((3R,8aR)-3-isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione)