NP-MRD: Showing NP-Card for Colletopiperazine (NP0009276)

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Record Information

Version

2.0

Created at

2020-12-09 06:40:47 UTC

Updated at

2021-07-15 17:02:48 UTC

NP-MRD ID

NP0009276

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Colletopiperazine

Provided By

NPAtlas

Description

Colletopiperazine belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole. Colletopiperazine is found in Colletotrichum gloeosporioides. Colletopiperazine was first documented in 2010 (PMID: 20541231). Based on a literature review very few articles have been published on Colletopiperazine.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106343D          

 37 39  0  0  0  0            999 V2000
   -2.8339   -0.5812    2.3543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2556   -0.7780    0.6273 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9641   -0.2474   -0.5020 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4950   -0.4869   -1.9197 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8079   -1.8316   -2.1080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7171   -1.0097   -0.3543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6870   -2.2526   -0.1370 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5288   -0.3329   -0.4580 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8169   -0.5005    0.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2601   -1.4843    0.9881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4085   -2.4902    1.3998 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5701   -1.4187    1.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4427   -0.4358    1.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9816    0.5328    0.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6795    0.5206   -0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9449    1.4303   -1.2045 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5996    0.8281   -1.3612 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5117    1.7157   -1.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4345    2.9477   -1.2504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6610    1.1621   -0.3777 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5174    2.0596    0.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0016    0.4444    2.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8245   -0.9638    2.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5447   -1.2326    2.9443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4769    0.0624   -2.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7841   -0.1921   -2.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1225   -2.3147   -2.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6465   -3.2309    2.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9517   -2.1786    2.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4787   -0.4140    1.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6133    1.3407   -0.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9456    2.4742   -0.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5317    1.4325   -2.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4888    0.5104   -2.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7771    2.9135   -0.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4380    1.5316    0.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0346    2.4697    1.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20  3  1  0  0  0  0
 17  8  1  0  0  0  0
 15  9  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  4 25  1  0  0  0  0
  4 26  1  0  0  0  0
  5 27  1  0  0  0  0
 11 28  1  0  0  0  0
 12 29  1  0  0  0  0
 13 30  1  0  0  0  0
 14 31  1  0  0  0  0
 16 32  1  0  0  0  0
 16 33  1  0  0  0  0
 17 34  1  6  0  0  0
 21 35  1  0  0  0  0
 21 36  1  0  0  0  0
 21 37  1  0  0  0  0
M  END

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
   -2.8339   -0.5812    2.3543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2556   -0.7780    0.6273 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9641   -0.2474   -0.5020 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4950   -0.4869   -1.9197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8079   -1.8316   -2.1080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7171   -1.0097   -0.3543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6870   -2.2526   -0.1370 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5288   -0.3329   -0.4580 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8169   -0.5005    0.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2601   -1.4843    0.9881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4085   -2.4902    1.3998 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5701   -1.4187    1.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4427   -0.4358    1.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9816    0.5328    0.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6795    0.5206   -0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9449    1.4303   -1.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5996    0.8281   -1.3612 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5117    1.7157   -1.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4345    2.9477   -1.2504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6610    1.1621   -0.3777 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5174    2.0596    0.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0016    0.4444    2.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8245   -0.9638    2.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5447   -1.2326    2.9443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4769    0.0624   -2.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7841   -0.1921   -2.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1225   -2.3147   -2.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6465   -3.2309    2.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9517   -2.1786    2.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4787   -0.4140    1.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6133    1.3407   -0.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9456    2.4742   -0.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5317    1.4325   -2.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4888    0.5104   -2.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7771    2.9135   -0.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4380    1.5316    0.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0346    2.4697    1.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20  3  1  0
 17  8  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  6
 21 35  1  0
 21 36  1  0
 21 37  1  0
M  END


  Mrv1652306242106343D          

 37 39  0  0  0  0            999 V2000
   -2.8339   -0.5812    2.3543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2556   -0.7780    0.6273 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9641   -0.2474   -0.5020 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4950   -0.4869   -1.9197 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8079   -1.8316   -2.1080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7171   -1.0097   -0.3543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6870   -2.2526   -0.1370 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5288   -0.3329   -0.4580 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8169   -0.5005    0.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2601   -1.4843    0.9881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4085   -2.4902    1.3998 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5701   -1.4187    1.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4427   -0.4358    1.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9816    0.5328    0.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6795    0.5206   -0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9449    1.4303   -1.2045 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5996    0.8281   -1.3612 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5117    1.7157   -1.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4345    2.9477   -1.2504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6610    1.1621   -0.3777 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5174    2.0596    0.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0016    0.4444    2.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8245   -0.9638    2.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5447   -1.2326    2.9443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4769    0.0624   -2.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7841   -0.1921   -2.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1225   -2.3147   -2.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6465   -3.2309    2.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9517   -2.1786    2.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4787   -0.4140    1.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6133    1.3407   -0.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9456    2.4742   -0.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5317    1.4325   -2.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4888    0.5104   -2.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7771    2.9135   -0.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4380    1.5316    0.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0346    2.4697    1.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20  3  1  0  0  0  0
 17  8  1  0  0  0  0
 15  9  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  4 25  1  0  0  0  0
  4 26  1  0  0  0  0
  5 27  1  0  0  0  0
 11 28  1  0  0  0  0
 12 29  1  0  0  0  0
 13 30  1  0  0  0  0
 14 31  1  0  0  0  0
 16 32  1  0  0  0  0
 16 33  1  0  0  0  0
 17 34  1  6  0  0  0
 21 35  1  0  0  0  0
 21 36  1  0  0  0  0
 21 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0009276

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2N3C(=O)[C@@](SC([H])([H])[H])(N(C(=O)[C@@]3([H])C([H])([H])C2=C([H])C([H])=C1[H])C([H])([H])[H])C([H])([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C14H16N2O4S/c1-15-12(19)9-6-8-4-3-5-10(18)11(8)16(9)13(20)14(15,7-17)21-2/h3-5,9,17-18H,6-7H2,1-2H3/t9-,14-/m1/s1

> <INCHI_KEY>
HLTTVBPDCRSKFJ-IWSPRGBSSA-N

> <FORMULA>
C14H16N2O4S

> <MOLECULAR_WEIGHT>
308.35

> <EXACT_MASS>
308.083078177

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
30.623887562313392

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,10aR)-6-hydroxy-3-(hydroxymethyl)-2-methyl-3-(methylsulfanyl)-1H,2H,3H,4H,10H,10aH-pyrazino[1,2-a]indole-1,4-dione

> <ALOGPS_LOGP>
0.12

> <JCHEM_LOGP>
0.7582057019999999

> <ALOGPS_LOGS>
-1.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.166300262551786

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.580450197800197

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1542499245361633

> <JCHEM_POLAR_SURFACE_AREA>
81.08

> <JCHEM_REFRACTIVITY>
78.5718

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.10e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,10aR)-6-hydroxy-3-(hydroxymethyl)-2-methyl-3-(methylsulfanyl)-10H,10aH-pyrazino[1,2-a]indole-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
   -2.8339   -0.5812    2.3543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2556   -0.7780    0.6273 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9641   -0.2474   -0.5020 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4950   -0.4869   -1.9197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8079   -1.8316   -2.1080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7171   -1.0097   -0.3543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6870   -2.2526   -0.1370 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5288   -0.3329   -0.4580 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8169   -0.5005    0.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2601   -1.4843    0.9881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4085   -2.4902    1.3998 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5701   -1.4187    1.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4427   -0.4358    1.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9816    0.5328    0.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6795    0.5206   -0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9449    1.4303   -1.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5996    0.8281   -1.3612 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5117    1.7157   -1.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4345    2.9477   -1.2504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6610    1.1621   -0.3777 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5174    2.0596    0.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0016    0.4444    2.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8245   -0.9638    2.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5447   -1.2326    2.9443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4769    0.0624   -2.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7841   -0.1921   -2.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1225   -2.3147   -2.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6465   -3.2309    2.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9517   -2.1786    2.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4787   -0.4140    1.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6133    1.3407   -0.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9456    2.4742   -0.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5317    1.4325   -2.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4888    0.5104   -2.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7771    2.9135   -0.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4380    1.5316    0.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0346    2.4697    1.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20  3  1  0
 17  8  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  6
 21 35  1  0
 21 36  1  0
 21 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  C   UNK     0      -2.834  -0.581   2.354  0.00  0.00           C+0
HETATM    2  S   UNK     0      -3.256  -0.778   0.627  0.00  0.00           S+0
HETATM    3  C   UNK     0      -1.964  -0.247  -0.502  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.495  -0.487  -1.920  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.808  -1.832  -2.108  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.717  -1.010  -0.354  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.687  -2.253  -0.137  0.00  0.00           O+0
HETATM    8  N   UNK     0       0.529  -0.333  -0.458  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.817  -0.500   0.127  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.260  -1.484   0.988  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.409  -2.490   1.400  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.570  -1.419   1.413  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.443  -0.436   1.025  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.982   0.533   0.168  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.680   0.521  -0.292  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.945   1.430  -1.204  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.600   0.828  -1.361  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.512   1.716  -1.002  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.435   2.948  -1.250  0.00  0.00           O+0
HETATM   20  N   UNK     0      -1.661   1.162  -0.378  0.00  0.00           N+0
HETATM   21  C   UNK     0      -2.517   2.060   0.387  0.00  0.00           C+0
HETATM   22  H   UNK     0      -3.002   0.444   2.739  0.00  0.00           H+0
HETATM   23  H   UNK     0      -1.825  -0.964   2.614  0.00  0.00           H+0
HETATM   24  H   UNK     0      -3.545  -1.233   2.944  0.00  0.00           H+0
HETATM   25  H   UNK     0      -3.477   0.062  -2.018  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.784  -0.192  -2.696  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.123  -2.315  -2.618  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.647  -3.231   2.014  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.952  -2.179   2.092  0.00  0.00           H+0
HETATM   30  H   UNK     0       5.479  -0.414   1.383  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.613   1.341  -0.181  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.946   2.474  -0.854  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.532   1.433  -2.167  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.489   0.510  -2.421  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.777   2.914  -0.272  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.438   1.532   0.644  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.035   2.470   1.274  0.00  0.00           H+0
CONECT    1    2   22   23   24                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    6   20                                             
CONECT    4    3    5   25   26                                             
CONECT    5    4   27                                                       
CONECT    6    3    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   17                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10   28                                                       
CONECT   12   10   13   29                                                  
CONECT   13   12   14   30                                                  
CONECT   14   13   15   31                                                  
CONECT   15   14   16    9                                                  
CONECT   16   15   17   32   33                                             
CONECT   17   16   18    8   34                                             
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21    3                                                  
CONECT   21   20   35   36   37                                             
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    4                                                            
CONECT   26    4                                                            
CONECT   27    5                                                            
CONECT   28   11                                                            
CONECT   29   12                                                            
CONECT   30   13                                                            
CONECT   31   14                                                            
CONECT   32   16                                                            
CONECT   33   16                                                            
CONECT   34   17                                                            
CONECT   35   21                                                            
CONECT   36   21                                                            
CONECT   37   21                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

RDKit          3D

37 39  0  0  0  0  0  0  0  0999 V2000
   -2.8339   -0.5812    2.3543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2556   -0.7780    0.6273 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9641   -0.2474   -0.5020 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4950   -0.4869   -1.9197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8079   -1.8316   -2.1080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7171   -1.0097   -0.3543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6870   -2.2526   -0.1370 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5288   -0.3329   -0.4580 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8169   -0.5005    0.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2601   -1.4843    0.9881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4085   -2.4902    1.3998 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5701   -1.4187    1.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4427   -0.4358    1.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9816    0.5328    0.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6795    0.5206   -0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9449    1.4303   -1.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5996    0.8281   -1.3612 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5117    1.7157   -1.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4345    2.9477   -1.2504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6610    1.1621   -0.3777 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5174    2.0596    0.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0016    0.4444    2.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8245   -0.9638    2.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5447   -1.2326    2.9443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4769    0.0624   -2.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7841   -0.1921   -2.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1225   -2.3147   -2.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6465   -3.2309    2.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9517   -2.1786    2.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4787   -0.4140    1.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6133    1.3407   -0.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9456    2.4742   -0.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5317    1.4325   -2.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4888    0.5104   -2.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7771    2.9135   -0.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4380    1.5316    0.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0346    2.4697    1.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20  3  1  0
 17  8  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  6
 21 35  1  0
 21 36  1  0
 21 37  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(3R)-6-Hydroxy-3-(hydroxymethyl)-2-methyl-3-(methylsulphanyl)-1H,2H,3H,4H,10H,10ah-pyrazino[1,2-a]indole-1,4-dione	Generator

Chemical Formula

C₁₄H₁₆N₂O₄S

Average Mass

308.3500 Da

Monoisotopic Mass

308.08308 Da

IUPAC Name

(3R,10aR)-6-hydroxy-3-(hydroxymethyl)-2-methyl-3-(methylsulfanyl)-1H,2H,3H,4H,10H,10aH-pyrazino[1,2-a]indole-1,4-dione

Traditional Name

(3R,10aR)-6-hydroxy-3-(hydroxymethyl)-2-methyl-3-(methylsulfanyl)-10H,10aH-pyrazino[1,2-a]indole-1,4-dione

CAS Registry Number

Not Available

SMILES

CS[C@@]1(CO)N(C)C(=O)C2CC3=C(N2C1=O)C(O)=CC=C3

InChI Identifier

InChI=1S/C14H16N2O4S/c1-15-12(19)9-6-8-4-3-5-10(18)11(8)16(9)13(20)14(15,7-17)21-2/h3-5,9,17-18H,6-7H2,1-2H3/t9?,14-/m1/s1

InChI Key

HLTTVBPDCRSKFJ-IWSPRGBSSA-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
Colletotrichum gloeosporioides	NPAtlas	20541231

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolecarboxylic acids and derivatives

Direct Parent

Indolecarboxylic acids and derivatives

Alternative Parents

Substituents

Indolecarboxylic acid derivative
Alpha-amino acid or derivatives
Thiodioxopiperazine
Dioxopiperazine
2,5-dioxopiperazine
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
N-methylpiperazine
N-alkylpiperazine
1,4-diazinane
Piperazine
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Dialkylthioether
Azacycle
Carboxylic acid derivative
Sulfenyl compound
Hemithioaminal
Thioether
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organosulfur compound
Organic nitrogen compound
Primary alcohol
Hydrocarbon derivative
Alcohol
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	0.12	ALOGPS
logP	0.76	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	8.58	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	81.08 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.57 m³·mol⁻¹	ChemAxon
Polarizability	30.62 Å³	ChemAxon
Number of Rings	3	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

NPAtlas ID

NPA009758

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78442625

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139585799

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Guimaraes DO, Borges WS, Vieira NJ, de Oliveira LF, da Silva CH, Lopes NP, Dias LG, Duran-Patron R, Collado IG, Pupo MT: Diketopiperazines produced by endophytic fungi found in association with two Asteraceae species. Phytochemistry. 2010 Aug;71(11-12):1423-9. doi: 10.1016/j.phytochem.2010.05.012. Epub 2010 Jun 10. [PubMed:20541231 ]

Showing NP-Card for Colletopiperazine (NP0009276)

MOL for NP0009276 (Colletopiperazine)

3D MOL for NP0009276 (Colletopiperazine)

3D SDF for NP0009276 (Colletopiperazine)

3D-SDF for NP0009276 (Colletopiperazine)

PDB for NP0009276 (Colletopiperazine)

3D PDB for NP0009276 (Colletopiperazine)

SMILES for NP0009276 (Colletopiperazine)

INCHI for NP0009276 (Colletopiperazine)

Structure for NP0009276 (Colletopiperazine)

3D Structure for NP0009276 (Colletopiperazine)