NP-MRD: Showing NP-Card for 10a-hydroxy-3-(hydroxymethyl)-2-methyl-3h,10h-pyrazino[1,2-a]indole-1,4-dione (NP0287617)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 16:52:04 UTC

Updated at

2022-09-09 16:52:04 UTC

NP-MRD ID

NP0287617

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10a-hydroxy-3-(hydroxymethyl)-2-methyl-3h,10h-pyrazino[1,2-a]indole-1,4-dione

Description

10A-hydroxy-3-(hydroxymethyl)-2-methyl-1H,2H,3H,4H,10H,10aH-pyrazino[1,2-a]indole-1,4-dione 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. 10a-hydroxy-3-(hydroxymethyl)-2-methyl-3h,10h-pyrazino[1,2-a]indole-1,4-dione is found in Aspergillus cejpii. Based on a literature review very few articles have been published on 10a-hydroxy-3-(hydroxymethyl)-2-methyl-1H,2H,3H,4H,10H,10aH-pyrazino[1,2-a]indole-1,4-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
   -3.6549   -0.9642   -0.2815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2609   -0.5049   -0.3006 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1911   -1.3750   -0.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3938   -2.4014   -1.2497 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1333   -1.0877    0.0209 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1513   -1.5173    1.3436 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2746   -1.6955   -0.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4086   -0.7824   -0.3993 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7906   -0.9161   -0.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6061    0.1261   -0.0938 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0909    1.3403    0.3469 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7125    1.4423    0.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8735    0.4030    0.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4473    0.3256    0.0169 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6222    1.2619    0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3064    2.4758    0.0399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0369    0.8995   -0.0568 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8192    1.2835    1.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6837    2.6171    1.5105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0561   -0.9172    0.7629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7150   -2.0449   -0.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2775   -0.4138   -1.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4613   -2.3098    1.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4758   -2.7342   -0.4160 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0628   -1.6390   -1.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1542   -1.8738   -0.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6862    0.0056   -0.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7443    2.1428    0.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2835    2.3957    0.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4911    1.4804   -0.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4837    0.6396    1.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9063    1.1272    0.9210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5354    3.2108    0.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 17  1  0
 17 18  1  0
 18 19  1  0
 17 15  1  0
 15 16  2  0
 15 14  1  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
 11 10  2  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  5  1  0
  5  6  1  1
  5  3  1  0
  3  4  2  0
  3  2  1  0
  5 14  1  0
  8 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 17 30  1  6
 18 31  1  0
 18 32  1  0
 19 33  1  0
 12 29  1  0
 11 28  1  0
 10 27  1  0
  9 26  1  0
  7 24  1  0
  7 25  1  0
  6 23  1  0
M  END


  Mrv1652309092218522D          

 19 21  0  0  0  0            999 V2000
    0.9130   -0.8764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7200   -1.0479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720   -0.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0171    0.3498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9075    0.2006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7464   -0.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4139   -0.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2208   -0.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7729   -1.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5179   -1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7110   -2.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1589   -1.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339   -1.3910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7819   -2.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0368   -2.7887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9749   -1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4229   -2.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6778   -3.2303    0.0000 O   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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0287617

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(CO)C(=O)N2C3=CC=CC=C3CC2(O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H14N2O4/c1-14-10(7-16)11(17)15-9-5-3-2-4-8(9)6-13(15,19)12(14)18/h2-5,10,16,19H,6-7H2,1H3

> <INCHI_KEY>
FHJQHCKBAXMQOE-UHFFFAOYSA-N

> <FORMULA>
C13H14N2O4

> <MOLECULAR_WEIGHT>
262.265

> <EXACT_MASS>
262.095356939

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
25.86675555965913

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-0.5977531196666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.20280130977198

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.88726214623374

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8480716293560517

> <JCHEM_POLAR_SURFACE_AREA>
81.08000000000001

> <JCHEM_REFRACTIVITY>
65.92330000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       1.704  -1.636   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       3.211  -1.956   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       4.241  -0.812   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.765   0.653   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.747  -1.132   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.427   0.374   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.993  -0.227   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.239  -1.132   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.746  -0.812   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.776  -1.956   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.300  -3.421   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.794  -3.741   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.763  -2.597   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       6.223  -2.597   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       5.193  -3.741   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.669  -5.206   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.687  -3.421   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.656  -4.565   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.132  -6.030   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   14                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13    5   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    2   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₄N₂O₄

Average Mass

262.2650 Da

Monoisotopic Mass

262.09536 Da

IUPAC Name

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

Traditional Name

10a-hydroxy-3-(hydroxymethyl)-2-methyl-3H,10H-pyrazino[1,2-a]indole-1,4-dione

CAS Registry Number

Not Available

SMILES

CN1C(CO)C(=O)N2C3=CC=CC=C3CC2(O)C1=O

InChI Identifier

InChI=1S/C13H14N2O4/c1-14-10(7-16)11(17)15-9-5-3-2-4-8(9)6-13(15,19)12(14)18/h2-5,10,16,19H,6-7H2,1H3

InChI Key

FHJQHCKBAXMQOE-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Aspergillus cejpii	LOTUS Database	35616633

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
Dioxopiperazine
2,5-dioxopiperazine
N-methylpiperazine
N-alkylpiperazine
1,4-diazinane
Piperazine
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Azacycle
Alkanolamine
Carboxylic acid derivative
Organic oxide
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Alcohol
Organooxygen compound
Primary alcohol
Carbonyl group
Hydrocarbon derivative
Organic nitrogen compound
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	-0.6	ChemAxon
pKa (Strongest Acidic)	10.89	ChemAxon
pKa (Strongest Basic)	-2.8	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	1	ChemAxon
Refractivity	65.92 m³·mol⁻¹	ChemAxon
Polarizability	25.87 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163065300

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10a-hydroxy-3-(hydroxymethyl)-2-methyl-3h,10h-pyrazino[1,2-a]indole-1,4-dione (NP0287617)

MOL for NP0287617 (10a-hydroxy-3-(hydroxymethyl)-2-methyl-3h,10h-pyrazino[1,2-a]indole-1,4-dione)

3D MOL for NP0287617 (10a-hydroxy-3-(hydroxymethyl)-2-methyl-3h,10h-pyrazino[1,2-a]indole-1,4-dione)

3D SDF for NP0287617 (10a-hydroxy-3-(hydroxymethyl)-2-methyl-3h,10h-pyrazino[1,2-a]indole-1,4-dione)

3D-SDF for NP0287617 (10a-hydroxy-3-(hydroxymethyl)-2-methyl-3h,10h-pyrazino[1,2-a]indole-1,4-dione)

PDB for NP0287617 (10a-hydroxy-3-(hydroxymethyl)-2-methyl-3h,10h-pyrazino[1,2-a]indole-1,4-dione)

3D PDB for NP0287617 (10a-hydroxy-3-(hydroxymethyl)-2-methyl-3h,10h-pyrazino[1,2-a]indole-1,4-dione)

SMILES for NP0287617 (10a-hydroxy-3-(hydroxymethyl)-2-methyl-3h,10h-pyrazino[1,2-a]indole-1,4-dione)

INCHI for NP0287617 (10a-hydroxy-3-(hydroxymethyl)-2-methyl-3h,10h-pyrazino[1,2-a]indole-1,4-dione)

Structure for NP0287617 (10a-hydroxy-3-(hydroxymethyl)-2-methyl-3h,10h-pyrazino[1,2-a]indole-1,4-dione)

3D Structure for NP0287617 (10a-hydroxy-3-(hydroxymethyl)-2-methyl-3h,10h-pyrazino[1,2-a]indole-1,4-dione)