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Showing NP-Card for (3s,8as)-1-hydroxy-3-methyl-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one (NP0194116)

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Record Information
Version2.0
Created at2022-09-04 11:43:01 UTC
Updated at2022-09-04 11:43:01 UTC
NP-MRD IDNP0194116
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3s,8as)-1-hydroxy-3-methyl-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one
DescriptionCyclo(L-Ala-L-Pro) 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. (3s,8as)-1-hydroxy-3-methyl-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one is found in Aspergillus fumigatus and Nigrospora oryzae. (3s,8as)-1-hydroxy-3-methyl-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one was first documented in 2016 (PMID: 26376763). Based on a literature review a small amount of articles have been published on Cyclo(L-Ala-L-Pro) (PMID: 33224231) (PMID: 28704973).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0194116 ((3s,8as)-1-hydroxy-3-methyl-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one)


  Mrv1652309042213432D          

 12 13  0  0  1  0            999 V2000
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  6  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
Download

3D MOL for NP0194116 ((3s,8as)-1-hydroxy-3-methyl-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one)

     RDKit          3D

 24 25  0  0  0  0  0  0  0  0999 V2000
    3.3459   -0.3530    0.4430 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0103   -0.3973   -0.2651 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6218    0.9659   -0.5625 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4100    1.3529   -0.7394 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0977    2.6821   -1.0235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6824    0.3951   -0.6459 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9024    0.9632    0.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6677   -0.3057    0.3831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6593   -1.4237    0.3739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3959   -0.7481    0.1798 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9419   -0.9699    0.5998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1660   -1.6211    1.6531 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6508   -1.3550    0.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3041    0.3333    1.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0858    0.0082   -0.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0880   -1.0302   -1.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2793    3.2221   -0.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0017   -0.0030   -1.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4776    1.6455   -0.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5785    1.4422    1.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4189   -0.4369   -0.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1400   -0.2715    1.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8270   -2.0281   -0.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6915   -2.0671    1.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11  2  1  0
 10  6  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  6
  5 17  1  0
  6 18  1  6
  7 19  1  0
  7 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
M  END
Download

3D SDF for NP0194116 ((3s,8as)-1-hydroxy-3-methyl-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one)


  Mrv1652309042213432D          

 12 13  0  0  1  0            999 V2000
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  6  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0194116

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1N=C(O)[C@@H]2CCCN2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H12N2O2/c1-5-8(12)10-4-2-3-6(10)7(11)9-5/h5-6H,2-4H2,1H3,(H,9,11)/t5-,6-/m0/s1

> <INCHI_KEY>
WSLYCILIEOFQPK-WDSKDSINSA-N

> <FORMULA>
C8H12N2O2

> <MOLECULAR_WEIGHT>
168.196

> <EXACT_MASS>
168.089877634

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
17.015297821891266

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,8aS)-1-hydroxy-3-methyl-3H,4H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one

> <JCHEM_LOGP>
0.019231709999999985

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.606230738921701

> <JCHEM_PKA_STRONGEST_BASIC>
1.4348624776469416

> <JCHEM_POLAR_SURFACE_AREA>
52.900000000000006

> <JCHEM_REFRACTIVITY>
42.805600000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,8aS)-1-hydroxy-3-methyl-3H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0194116 ((3s,8as)-1-hydroxy-3-methyl-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one)

Download
PDB for NP0194116 ((3s,8as)-1-hydroxy-3-methyl-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one)
HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       6.258   2.073   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.590   3.613   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.924   5.923   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6   11                                                  
CONECT   11   10    2   12                                                  
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

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3D PDB for NP0194116 ((3s,8as)-1-hydroxy-3-methyl-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one)
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SMILES for NP0194116 ((3s,8as)-1-hydroxy-3-methyl-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one)
C[C@@H]1N=C(O)[C@@H]2CCCN2C1=O
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INCHI for NP0194116 ((3s,8as)-1-hydroxy-3-methyl-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one)
InChI=1S/C8H12N2O2/c1-5-8(12)10-4-2-3-6(10)7(11)9-5/h5-6H,2-4H2,1H3,(H,9,11)/t5-,6-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC8H12N2O2
Average Mass168.1960 Da
Monoisotopic Mass168.08988 Da
IUPAC Name(3S,8aS)-1-hydroxy-3-methyl-3H,4H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one
Traditional Name(3S,8aS)-1-hydroxy-3-methyl-3H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one
CAS Registry NumberNot Available
SMILES
C[C@@H]1N=C(O)[C@@H]2CCCN2C1=O
InChI Identifier
InChI=1S/C8H12N2O2/c1-5-8(12)10-4-2-3-6(10)7(11)9-5/h5-6H,2-4H2,1H3,(H,9,11)/t5-,6-/m0/s1
InChI KeyWSLYCILIEOFQPK-WDSKDSINSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aspergillus fumigatusLOTUS Database
Nigrospora oryzaeLOTUS Database
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.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentAlpha 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
    • 

  • Secondary carboxylic acid amide
    • 

  • Lactam
    • 

  • Carboxamide group
    • 

  • Azacycle
    • 

  • Organoheterocyclic compound
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.019ChemAxon
pKa (Strongest Acidic)4.61ChemAxon
pKa (Strongest Basic)1.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.9 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity42.81 m³·mol⁻¹ChemAxon
Polarizability17.02 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10259492  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13879951  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Yang ZD, Zhang Y, Zhao WH, Shu ZM: Chemical Composition and Biological Activities of Endophytic Fungus Talaromyces Wortmannii LGT-4, Cultured in CYM Medium. Iran J Pharm Res. 2020 Spring;19(2):259-263. doi: 10.22037/ijpr.2020.1101051. [PubMed:33224231  ] 
  2. Iimura K, Furukawa T, Yamamoto T, Negishi L, Suzuki M, Sakuda S: The Mode of Action of Cyclo(l-Ala-l-Pro) in Inhibiting Aflatoxin Production of Aspergillus flavus. Toxins (Basel). 2017 Jul 12;9(7):219. doi: 10.3390/toxins9070219. [PubMed:28704973  ] 
  3. Sakuda S, Yoshinari T, Furukawa T, Jermnak U, Takagi K, Iimura K, Yamamoto T, Suzuki M, Nagasawa H: Search for aflatoxin and trichothecene production inhibitors and analysis of their modes of action. Biosci Biotechnol Biochem. 2016;80(1):43-54. doi: 10.1080/09168451.2015.1086261.  Epub 2015 Sep 17. [PubMed:26376763  ] 
  4. LOTUS database [Link]