NP-MRD: Showing NP-Card for Cyclo(4-hydroxy-S-Pro-S-Trp) (NP0010395)

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Record Information

Version

1.0

Created at

2021-01-05 19:55:50 UTC

Updated at

2021-07-15 17:05:58 UTC

NP-MRD ID

NP0010395

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cyclo(4-hydroxy-S-Pro-S-Trp)

Provided By

NPAtlas

Description

(3S,8aS)-1,7-dihydroxy-3-[(1H-indol-3-yl)methyl]-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. Cyclo(4-hydroxy-S-Pro-S-Trp) is found in Streptomyces sp. It was first documented in 2011 (PMID: 21985013). Based on a literature review very few articles have been published on (3S,8aS)-1,7-dihydroxy-3-[(1H-indol-3-yl)methyl]-3H,4H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one (PMID: 34383398) (PMID: 34383397) (PMID: 34383396) (PMID: 34384147) (PMID: 34384146) (PMID: 34384145).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242107373D          

 39 42  0  0  0  0            999 V2000
    2.7760   -2.6871   -1.5795 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2325   -1.5465   -1.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8637   -1.4346   -1.8744 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0117   -0.5043   -1.1967 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7518   -1.3333   -0.1375 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6941   -0.4501    0.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5264    0.0505    1.9014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5928    0.7883    2.2045 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4751    0.8165    1.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6980    1.4366    1.0709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3742    1.2605   -0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8233    0.4802   -1.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6111   -0.1252   -0.9745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9127    0.0329    0.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7294    0.5460   -0.4685 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1186    1.5975   -0.1419 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1070    0.3976   -0.1301 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8998    0.8793    1.0136 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3139    0.6023    0.5952 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1750    0.4633    1.6802 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1639   -0.6945   -0.1814 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9462   -0.3543   -1.0336 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4500   -2.0171   -2.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7607   -0.0572   -1.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0006   -1.7652    0.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2923   -2.1717   -0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6536   -0.1521    2.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7166    1.2853    3.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1602    2.0493    1.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3362    1.7064   -0.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3599    0.3403   -2.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1485   -0.7460   -1.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6974    1.9387    1.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6835    0.2201    1.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6326    1.4003   -0.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9346   -0.1171    1.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8716   -1.4769    0.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0363   -0.9433   -0.7797 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2682    0.2847   -1.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  4 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22  2  1  0  0  0  0
 14  6  1  0  0  0  0
 22 17  1  0  0  0  0
 14  9  1  0  0  0  0
  3 23  1  0  0  0  0
  4 24  1  6  0  0  0
  5 25  1  0  0  0  0
  5 26  1  0  0  0  0
  7 27  1  0  0  0  0
  8 28  1  0  0  0  0
 10 29  1  0  0  0  0
 11 30  1  0  0  0  0
 12 31  1  0  0  0  0
 13 32  1  0  0  0  0
 18 33  1  0  0  0  0
 18 34  1  0  0  0  0
 19 35  1  6  0  0  0
 20 36  1  0  0  0  0
 21 37  1  0  0  0  0
 21 38  1  0  0  0  0
 22 39  1  6  0  0  0
M  END

     RDKit          3D

 39 42  0  0  0  0  0  0  0  0999 V2000
    2.7760   -2.6871   -1.5795 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2325   -1.5465   -1.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8637   -1.4346   -1.8744 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0117   -0.5043   -1.1967 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7518   -1.3333   -0.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6941   -0.4501    0.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5264    0.0505    1.9014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5928    0.7883    2.2045 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4751    0.8165    1.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6980    1.4366    1.0709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3742    1.2605   -0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8233    0.4802   -1.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6111   -0.1252   -0.9745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9127    0.0329    0.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7294    0.5460   -0.4685 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1186    1.5975   -0.1419 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1070    0.3976   -0.1301 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8998    0.8793    1.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3139    0.6023    0.5952 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1750    0.4633    1.6802 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1639   -0.6945   -0.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9462   -0.3543   -1.0336 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4500   -2.0171   -2.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7607   -0.0572   -1.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0006   -1.7652    0.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2923   -2.1717   -0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6536   -0.1521    2.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7166    1.2853    3.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1602    2.0493    1.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3362    1.7064   -0.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3599    0.3403   -2.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1485   -0.7460   -1.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6974    1.9387    1.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6835    0.2201    1.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6326    1.4003   -0.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9346   -0.1171    1.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8716   -1.4769    0.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0363   -0.9433   -0.7797 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2682    0.2847   -1.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  4 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22  2  1  0
 14  6  1  0
 22 17  1  0
 14  9  1  0
  3 23  1  0
  4 24  1  6
  5 25  1  0
  5 26  1  0
  7 27  1  0
  8 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 18 33  1  0
 18 34  1  0
 19 35  1  6
 20 36  1  0
 21 37  1  0
 21 38  1  0
 22 39  1  6
M  END


  Mrv1652306242107373D          

 39 42  0  0  0  0            999 V2000
    2.7760   -2.6871   -1.5795 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2325   -1.5465   -1.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8637   -1.4346   -1.8744 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0117   -0.5043   -1.1967 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7518   -1.3333   -0.1375 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6941   -0.4501    0.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5264    0.0505    1.9014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5928    0.7883    2.2045 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4751    0.8165    1.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6980    1.4366    1.0709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3742    1.2605   -0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8233    0.4802   -1.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6111   -0.1252   -0.9745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9127    0.0329    0.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7294    0.5460   -0.4685 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1186    1.5975   -0.1419 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1070    0.3976   -0.1301 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8998    0.8793    1.0136 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3139    0.6023    0.5952 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1750    0.4633    1.6802 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1639   -0.6945   -0.1814 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9462   -0.3543   -1.0336 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4500   -2.0171   -2.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7607   -0.0572   -1.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0006   -1.7652    0.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2923   -2.1717   -0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6536   -0.1521    2.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7166    1.2853    3.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1602    2.0493    1.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3362    1.7064   -0.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3599    0.3403   -2.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1485   -0.7460   -1.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6974    1.9387    1.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6835    0.2201    1.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6326    1.4003   -0.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9346   -0.1171    1.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8716   -1.4769    0.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0363   -0.9433   -0.7797 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2682    0.2847   -1.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  4 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22  2  1  0  0  0  0
 14  6  1  0  0  0  0
 22 17  1  0  0  0  0
 14  9  1  0  0  0  0
  3 23  1  0  0  0  0
  4 24  1  6  0  0  0
  5 25  1  0  0  0  0
  5 26  1  0  0  0  0
  7 27  1  0  0  0  0
  8 28  1  0  0  0  0
 10 29  1  0  0  0  0
 11 30  1  0  0  0  0
 12 31  1  0  0  0  0
 13 32  1  0  0  0  0
 18 33  1  0  0  0  0
 18 34  1  0  0  0  0
 19 35  1  6  0  0  0
 20 36  1  0  0  0  0
 21 37  1  0  0  0  0
 21 38  1  0  0  0  0
 22 39  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0010395

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C([H])([H])N2C(=O)[C@@]([H])(N([H])C(=O)[C@]2([H])C1([H])[H])C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12

> <INCHI_IDENTIFIER>
InChI=1S/C16H17N3O3/c20-10-6-14-15(21)18-13(16(22)19(14)8-10)5-9-7-17-12-4-2-1-3-11(9)12/h1-4,7,10,13-14,17,20H,5-6,8H2,(H,18,21)/t10-,13-,14-/m0/s1

> <INCHI_KEY>
NKMYDIXLLZQYJO-RYQGGHCKSA-N

> <FORMULA>
C16H17N3O3

> <MOLECULAR_WEIGHT>
299.33

> <EXACT_MASS>
299.126991419

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
30.946471494190426

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,7S,8aS)-7-hydroxy-3-[(1H-indol-3-yl)methyl]-octahydropyrrolo[1,2-a]pyrazine-1,4-dione

> <ALOGPS_LOGP>
0.21

> <JCHEM_LOGP>
-0.19298166933333338

> <ALOGPS_LOGS>
-1.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.801805802288175

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.238441018217632

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8876986217657263

> <JCHEM_POLAR_SURFACE_AREA>
85.43

> <JCHEM_REFRACTIVITY>
79.30730000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.21e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,7S,8aS)-7-hydroxy-3-(1H-indol-3-ylmethyl)-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 39 42  0  0  0  0  0  0  0  0999 V2000
    2.7760   -2.6871   -1.5795 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2325   -1.5465   -1.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8637   -1.4346   -1.8744 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0117   -0.5043   -1.1967 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7518   -1.3333   -0.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6941   -0.4501    0.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5264    0.0505    1.9014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5928    0.7883    2.2045 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4751    0.8165    1.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6980    1.4366    1.0709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3742    1.2605   -0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8233    0.4802   -1.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6111   -0.1252   -0.9745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9127    0.0329    0.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7294    0.5460   -0.4685 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1186    1.5975   -0.1419 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1070    0.3976   -0.1301 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8998    0.8793    1.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3139    0.6023    0.5952 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1750    0.4633    1.6802 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1639   -0.6945   -0.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9462   -0.3543   -1.0336 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4500   -2.0171   -2.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7607   -0.0572   -1.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0006   -1.7652    0.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2923   -2.1717   -0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6536   -0.1521    2.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7166    1.2853    3.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1602    2.0493    1.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3362    1.7064   -0.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3599    0.3403   -2.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1485   -0.7460   -1.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6974    1.9387    1.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6835    0.2201    1.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6326    1.4003   -0.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9346   -0.1171    1.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8716   -1.4769    0.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0363   -0.9433   -0.7797 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2682    0.2847   -1.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  4 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22  2  1  0
 14  6  1  0
 22 17  1  0
 14  9  1  0
  3 23  1  0
  4 24  1  6
  5 25  1  0
  5 26  1  0
  7 27  1  0
  8 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 18 33  1  0
 18 34  1  0
 19 35  1  6
 20 36  1  0
 21 37  1  0
 21 38  1  0
 22 39  1  6
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  O   UNK     0       2.776  -2.687  -1.579  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.232  -1.547  -1.496  0.00  0.00           C+0
HETATM    3  N   UNK     0       0.864  -1.435  -1.874  0.00  0.00           N+0
HETATM    4  C   UNK     0      -0.012  -0.504  -1.197  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.752  -1.333  -0.138  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.694  -0.450   0.627  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.526   0.051   1.901  0.00  0.00           C+0
HETATM    8  N   UNK     0      -2.593   0.788   2.204  0.00  0.00           N+0
HETATM    9  C   UNK     0      -3.475   0.817   1.207  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.698   1.437   1.071  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.374   1.260  -0.117  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.823   0.480  -1.129  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.611  -0.125  -0.975  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.913   0.033   0.201  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.729   0.546  -0.469  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.119   1.597  -0.142  0.00  0.00           O+0
HETATM   17  N   UNK     0       2.107   0.398  -0.130  0.00  0.00           N+0
HETATM   18  C   UNK     0       2.900   0.879   1.014  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.314   0.602   0.595  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.175   0.463   1.680  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.164  -0.695  -0.181  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.946  -0.354  -1.034  0.00  0.00           C+0
HETATM   23  H   UNK     0       0.450  -2.017  -2.649  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.761  -0.057  -1.879  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.001  -1.765   0.555  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.292  -2.172  -0.614  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.654  -0.152   2.514  0.00  0.00           H+0
HETATM   28  H   UNK     0      -2.717   1.285   3.123  0.00  0.00           H+0
HETATM   29  H   UNK     0      -5.160   2.049   1.831  0.00  0.00           H+0
HETATM   30  H   UNK     0      -6.336   1.706  -0.314  0.00  0.00           H+0
HETATM   31  H   UNK     0      -5.360   0.340  -2.071  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.148  -0.746  -1.752  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.697   1.939   1.224  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.684   0.220   1.901  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.633   1.400  -0.099  0.00  0.00           H+0
HETATM   36  H   UNK     0       5.935  -0.117   1.361  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.872  -1.477   0.556  0.00  0.00           H+0
HETATM   38  H   UNK     0       5.036  -0.943  -0.780  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.268   0.285  -1.884  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4   23                                                  
CONECT    4    3    5   15   24                                             
CONECT    5    4    6   25   26                                             
CONECT    6    5    7   14                                                  
CONECT    7    6    8   27                                                  
CONECT    8    7    9   28                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11   29                                                  
CONECT   11   10   12   30                                                  
CONECT   12   11   13   31                                                  
CONECT   13   12   14   32                                                  
CONECT   14   13    6    9                                                  
CONECT   15    4   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   22                                                  
CONECT   18   17   19   33   34                                             
CONECT   19   18   20   21   35                                             
CONECT   20   19   36                                                       
CONECT   21   19   22   37   38                                             
CONECT   22   21    2   17   39                                             
CONECT   23    3                                                            
CONECT   24    4                                                            
CONECT   25    5                                                            
CONECT   26    5                                                            
CONECT   27    7                                                            
CONECT   28    8                                                            
CONECT   29   10                                                            
CONECT   30   11                                                            
CONECT   31   12                                                            
CONECT   32   13                                                            
CONECT   33   18                                                            
CONECT   34   18                                                            
CONECT   35   19                                                            
CONECT   36   20                                                            
CONECT   37   21                                                            
CONECT   38   21                                                            
CONECT   39   22                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

RDKit          3D

39 42  0  0  0  0  0  0  0  0999 V2000
    2.7760   -2.6871   -1.5795 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2325   -1.5465   -1.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8637   -1.4346   -1.8744 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0117   -0.5043   -1.1967 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7518   -1.3333   -0.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6941   -0.4501    0.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5264    0.0505    1.9014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5928    0.7883    2.2045 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4751    0.8165    1.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6980    1.4366    1.0709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3742    1.2605   -0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8233    0.4802   -1.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6111   -0.1252   -0.9745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9127    0.0329    0.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7294    0.5460   -0.4685 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1186    1.5975   -0.1419 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1070    0.3976   -0.1301 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8998    0.8793    1.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3139    0.6023    0.5952 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1750    0.4633    1.6802 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1639   -0.6945   -0.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9462   -0.3543   -1.0336 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4500   -2.0171   -2.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7607   -0.0572   -1.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0006   -1.7652    0.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2923   -2.1717   -0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6536   -0.1521    2.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7166    1.2853    3.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1602    2.0493    1.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3362    1.7064   -0.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3599    0.3403   -2.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1485   -0.7460   -1.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6974    1.9387    1.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6835    0.2201    1.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6326    1.4003   -0.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9346   -0.1171    1.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8716   -1.4769    0.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0363   -0.9433   -0.7797 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2682    0.2847   -1.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  4 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22  2  1  0
 14  6  1  0
 22 17  1  0
 14  9  1  0
  3 23  1  0
  4 24  1  6
  5 25  1  0
  5 26  1  0
  7 27  1  0
  8 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 18 33  1  0
 18 34  1  0
 19 35  1  6
 20 36  1  0
 21 37  1  0
 21 38  1  0
 22 39  1  6
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₆H₁₇N₃O₃

Average Mass

299.3300 Da

Monoisotopic Mass

299.12699 Da

IUPAC Name

(3S,7S,8aS)-7-hydroxy-3-[(1H-indol-3-yl)methyl]-octahydropyrrolo[1,2-a]pyrazine-1,4-dione

Traditional Name

(3S,7S,8aS)-7-hydroxy-3-(1H-indol-3-ylmethyl)-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

CAS Registry Number

Not Available

SMILES

OC1C[C@@H]2N(C1)C(=O)[C@H](CC1=CNC3=CC=CC=C13)NC2=O

InChI Identifier

InChI=1S/C16H17N3O3/c20-10-6-14-15(21)18-13(16(22)19(14)8-10)5-9-7-17-12-4-2-1-3-11(9)12/h1-4,7,10,13-14,17,20H,5-6,8H2,(H,18,21)/t10?,13-,14-/m0/s1

InChI Key

NKMYDIXLLZQYJO-RYQGGHCKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces sp.	NPAtlas	21985013

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

3-alkylindole
Alpha-amino acid or derivatives
Indole or derivatives
Indole
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Cyclic carboximidic acid
Tertiary carboxylic acid amide
Pyrrolidine
Pyrrole
Secondary alcohol
Lactam
Carboxamide group
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	0.21	ALOGPS
logP	-0.19	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	11.24	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	85.43 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.31 m³·mol⁻¹	ChemAxon
Polarizability	30.95 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA004664

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

29214352

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139584395

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li B, Chen G, Bai J, Jing YK, Pei YH: A bisamide and four diketopiperazines from a marine-derived Streptomyces sp. J Asian Nat Prod Res. 2011 Dec;13(12):1146-50. doi: 10.1080/10286020.2011.617744. Epub 2011 Oct 10. [PubMed:21985013 ]
Mitchell PM: The cost-effectiveness of what in health and care?. 2021 Feb. [PubMed:34383398 ]
Authors unspecified: Ozanimod. 2012. [PubMed:34383397 ]
Authors unspecified: Ponesimod. 2012. [PubMed:34383396 ]
Lee J, Cho Y, Choi KH, Hwang I, Oh YL: Metastatic leiomyosarcoma of the thyroid gland: cytologic findings and differential diagnosis. J Pathol Transl Med. 2021 Aug 13. pii: jptm.2021.06.23. doi: 10.4132/jptm.2021.06.23. [PubMed:34384147 ]
Rossouw HM, Nagel SE, Pillay TS: Comparability of 11 different equations for estimating LDL cholesterol on different analysers. Clin Chem Lab Med. 2021 Aug 11. pii: cclm-2021-0747. doi: 10.1515/cclm-2021-0747. [PubMed:34384146 ]
Winkel P, Hilden J, Jakobsen JC, Lindschou J, Jensen GB, Kjoller E, Sajadieh A, Kastrup J, Kolmos HJ, Larsson A, Arnlov J, Bjerre M, Gluud C: A screening method to spot biomarkers that may warn of serious events in a chronic disease - illustrated by cardiological CLARICOR trial data. Clin Chem Lab Med. 2021 Aug 12. pii: cclm-2021-0333. doi: 10.1515/cclm-2021-0333. [PubMed:34384145 ]
Lombardi Y, Hiesse C, Ridel C, Touzot M: From combined heart-kidney to kidney transplantation program: what nephrologists should know about dilated cardiomyopathy. Transpl Int. 2021 Aug;34(8):1573-1575. doi: 10.1111/tri.13948. [PubMed:34384144 ]
Anderson LL, Heblinski M, Absalom NL, Hawkins NA, Bowen M, Benson MJ, Zhang F, Bahceci D, Doohan PT, Chebib M, McGregor IS, Kearney JA, Arnold JC: Cannabigerolic acid, a major biosynthetic precursor molecule in cannabis, exhibits divergent effects on seizures in mouse models of epilepsy. Br J Pharmacol. 2021 Aug 12. doi: 10.1111/bph.15661. [PubMed:34384142 ]
Kennedy LJ, Cukier S, Khoury L, Steeves D: 'You drink at home so they can go to work safely': A case study exploring alcohol marketing during the COVID-19 pandemic. Drug Alcohol Rev. 2021 Aug 12. doi: 10.1111/dar.13374. [PubMed:34384143 ]
Voerman E, Jaddoe VWV, Shokry E, Ruijter GJG, Felix JF, Koletzko B, Gaillard R: Associations of maternal and infant metabolite profiles with foetal growth and the odds of adverse birth outcomes. Pediatr Obes. 2021 Aug 12:e12844. doi: 10.1111/ijpo.12844. [PubMed:34384140 ]
Milakovic L, Hintermeier P, Liu Y, Barath E, Lercher J: Influence of intracrystalline ionic strength in MFI zeolites on aqueous phase dehydration of methylcyclohexanols. Angew Chem Int Ed Engl. 2021 Aug 12. doi: 10.1002/anie.202107947. [PubMed:34384139 ]
Chou KT, Tsai YL, Yeh WY, Chen YM, Huang N, Cheng HM: Risk of work-related injury in workers with obstructive sleep apnea: A systematic review and meta-analysis. J Sleep Res. 2021 Aug 12:e13446. doi: 10.1111/jsr.13446. [PubMed:34384138 ]

Showing NP-Card for Cyclo(4-hydroxy-S-Pro-S-Trp) (NP0010395)

MOL for NP0010395 (Cyclo(4-hydroxy-S-Pro-S-Trp))

3D MOL for NP0010395 (Cyclo(4-hydroxy-S-Pro-S-Trp))

3D SDF for NP0010395 (Cyclo(4-hydroxy-S-Pro-S-Trp))

3D-SDF for NP0010395 (Cyclo(4-hydroxy-S-Pro-S-Trp))

PDB for NP0010395 (Cyclo(4-hydroxy-S-Pro-S-Trp))

3D PDB for NP0010395 (Cyclo(4-hydroxy-S-Pro-S-Trp))

SMILES for NP0010395 (Cyclo(4-hydroxy-S-Pro-S-Trp))

INCHI for NP0010395 (Cyclo(4-hydroxy-S-Pro-S-Trp))

Structure for NP0010395 (Cyclo(4-hydroxy-S-Pro-S-Trp))

3D Structure for NP0010395 (Cyclo(4-hydroxy-S-Pro-S-Trp))