NP-MRD: Showing NP-Card for 7-hydroxy-6-methylpyrimido[5,4-e][1,2,4]triazin-5-one (NP0291493)

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Record Information

Version

2.0

Created at

2022-09-09 22:36:41 UTC

Updated at

2022-09-09 22:36:41 UTC

NP-MRD ID

NP0291493

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-hydroxy-6-methylpyrimido[5,4-e][1,2,4]triazin-5-one

Description

Reumycin, also known as reumitsin, belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Reumycin is an extremely weak basic (essentially neutral) compound (based on its pKa). 7-hydroxy-6-methylpyrimido[5,4-e][1,2,4]triazin-5-one is found in Streptomyces hiroshimensis. 7-hydroxy-6-methylpyrimido[5,4-e][1,2,4]triazin-5-one was first documented in 1966 (PMID: 5907865). A pyrimidotriazine that is 6-methyl-5,6,7,8-tetrahydropyrimidotriazine with oxo groups at positions 5 and 6 (PMID: 1656661) (PMID: 3566230) (PMID: 4026251) (PMID: 4062279) (PMID: 4322358) (PMID: 4792066).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251510272D          

 13 14  0  0  0  0            999 V2000
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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
  6  7  2  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
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0291493

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(=O)NC2=NN=CN=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H5N5O2/c1-11-5(12)3-4(9-6(11)13)10-8-2-7-3/h2H,1H3,(H,9,10,13)

> <INCHI_KEY>
ZLLAXLPOOMLVRF-UHFFFAOYSA-N

> <FORMULA>
C6H5N5O2

> <MOLECULAR_WEIGHT>
179.139

> <EXACT_MASS>
179.044324421

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
15.183510133431179

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-methyl-5H,6H,7H,8H-pyrimido[5,4-e][1,2,4]triazine-5,7-dione

> <ALOGPS_LOGP>
-1.31

> <JCHEM_LOGP>
-0.3023488126666666

> <ALOGPS_LOGS>
-1.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.27600907715815

> <JCHEM_PKA_STRONGEST_BASIC>
-3.412390289231062

> <JCHEM_POLAR_SURFACE_AREA>
88.08000000000001

> <JCHEM_REFRACTIVITY>
45.1419

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.71e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-methyl-8H-pyrimido[5,4-e][1,2,4]triazine-5,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       2.667   0.000   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       5.335   0.000   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       6.668  -0.770   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       5.335  -3.080   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11    2   13                                                  
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol

Synonyms

Value	Source
1-Demethyltoxoflavin	ChEBI
6-Methyl-8H-pyrimido[5,4-e][1,2,4]triazine-5,7-dione	ChEBI
6-Methyl-pyrimido-[5,4-e]-as-triazine-5,7(6H,8H)-dione	ChEBI
Reumicine	ChEBI
Reumitsin	ChEBI
Rheumycin	ChEBI
Rheumygin	ChEBI

Chemical Formula

C₆H₅N₅O₂

Average Mass

179.1390 Da

Monoisotopic Mass

179.04432 Da

IUPAC Name

6-methyl-5H,6H,7H,8H-pyrimido[5,4-e][1,2,4]triazine-5,7-dione

Traditional Name

6-methyl-8H-pyrimido[5,4-e][1,2,4]triazine-5,7-dione

CAS Registry Number

Not Available

SMILES

CN1C(=O)NC2=NN=CN=C2C1=O

InChI Identifier

InChI=1S/C6H5N5O2/c1-11-5(12)3-4(9-6(11)13)10-8-2-7-3/h2H,1H3,(H,9,10,13)

InChI Key

ZLLAXLPOOMLVRF-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
Streptomyces hiroshimensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Pyrimidones

Alternative Parents

Substituents

Pyrimidone
Triazine
1,2,4-triazine
Heteroaromatic compound
Vinylogous amide
Lactam
Urea
Azacycle
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen 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	-1.3	ALOGPS
logP	-0.3	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	10.28	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	88.08 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	45.14 m³·mol⁻¹	ChemAxon
Polarizability	15.18 Å³	ChemAxon
Number of Rings	2	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

CPD-21062

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

121196

Good Scents ID

Not Available

References

General References

Romodanov SA, Semenova VM, Oleinik GM: [The antiblastic properties of reumycin (experimental research)]. Zh Vopr Neirokhir Im N N Burdenko. 1991 Mar-Apr;(2):13-6. [PubMed:1656661 ]
Sheina GG, Esipov SE, Ivanov AIu, Stepan'ian SG: [Structure and physicochemical properties of isolated molecules of reumycin]. Antibiot Med Biotekhnol. 1987 Feb;32(2):111-5. [PubMed:3566230 ]
Firsov AA, Geodakian SV, Terent'eva TG, Fomina IP: [Pharmacokinetics of the new antitumor antibiotic reumycin in an experiment: the prediction of the human pharmacokinetic profiles]. Antibiot Med Biotekhnol. 1985 Apr;30(4):296-301. [PubMed:4026251 ]
Firsov AA, Geodakian SV, Lichinitser MR, Shutka VIa: [Clinical pharmacokinetics of the antitumor antibiotic reumycin: an analysis of individual variability]. Antibiot Med Biotekhnol. 1985 Aug;30(8):604-8. [PubMed:4062279 ]
Shtegel'man LA: [Cytochemical analysis of the effect of antineoplastic antibiotic reumycin]. Antibiotiki. 1970 Nov;15(11):1021-5. [PubMed:4322358 ]
Esipov SE, Kolosov MN, Saburova LA: Letter: The structure of reumycin. J Antibiot (Tokyo). 1973 Sep;26(9):537-8. doi: 10.7164/antibiotics.26.537. [PubMed:4792066 ]
Liao TK, Baiocchi F, Cheng CC: Synthesis of 1-demethyltoxoflavin (8-demethylfervenulin). J Org Chem. 1966 Mar;31(3):900-2. doi: 10.1021/jo01341a061. [PubMed:5907865 ]
Svinogeeva TP, Berezina EK, Raiko LI: [Action of reumycin on the blood system in an experiment]. Antibiotiki. 1984 Jul;29(7):516-9. [PubMed:6486750 ]
LOTUS database [Link]

Showing NP-Card for 7-hydroxy-6-methylpyrimido[5,4-e][1,2,4]triazin-5-one (NP0291493)

MOL for NP0291493 (7-hydroxy-6-methylpyrimido[5,4-e][1,2,4]triazin-5-one)

3D MOL for NP0291493 (7-hydroxy-6-methylpyrimido[5,4-e][1,2,4]triazin-5-one)

3D SDF for NP0291493 (7-hydroxy-6-methylpyrimido[5,4-e][1,2,4]triazin-5-one)

3D-SDF for NP0291493 (7-hydroxy-6-methylpyrimido[5,4-e][1,2,4]triazin-5-one)

PDB for NP0291493 (7-hydroxy-6-methylpyrimido[5,4-e][1,2,4]triazin-5-one)

3D PDB for NP0291493 (7-hydroxy-6-methylpyrimido[5,4-e][1,2,4]triazin-5-one)

SMILES for NP0291493 (7-hydroxy-6-methylpyrimido[5,4-e][1,2,4]triazin-5-one)

INCHI for NP0291493 (7-hydroxy-6-methylpyrimido[5,4-e][1,2,4]triazin-5-one)

Structure for NP0291493 (7-hydroxy-6-methylpyrimido[5,4-e][1,2,4]triazin-5-one)

3D Structure for NP0291493 (7-hydroxy-6-methylpyrimido[5,4-e][1,2,4]triazin-5-one)