NP-MRD: Showing NP-Card for Flazine methyl ether (NP0047649)

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Record Information

Version

1.0

Created at

2022-03-17 20:43:40 UTC

Updated at

2022-03-17 20:43:40 UTC

NP-MRD ID

NP0047649

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Flazine methyl ether

Description

Flazine methyl ether, also known as proadifen or BCTB, belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole. Flazine methyl ether is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Flazine methyl ether is found, on average, in the highest concentration within blackcurrants. Flazine methyl ether has also been detected, but not quantified in, fruits. This could make flazine methyl ether a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307082D          

 24 27  0  0  0  0            999 V2000
    0.1624    5.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5800    3.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5800    2.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595    4.1012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2046    3.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2046    1.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896   -0.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339    1.5105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.5840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1966   -0.6422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1347   -1.5983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    4.7143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6895    2.6492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  7  6  1  0  0  0  0
 10  6  2  0  0  0  0
 10  9  1  0  0  0  0
 11  4  2  0  0  0  0
 12  8  2  0  0  0  0
 12 11  1  0  0  0  0
 13  5  2  0  0  0  0
 13 11  1  0  0  0  0
 14  8  1  0  0  0  0
 15  7  2  0  0  0  0
 16 12  1  0  0  0  0
 17 15  1  0  0  0  0
 17 16  2  0  0  0  0
 18 14  1  0  0  0  0
 19 13  1  0  0  0  0
 19 16  1  0  0  0  0
 20 14  2  0  0  0  0
 20 17  1  0  0  0  0
 21 18  1  0  0  0  0
 22 18  2  0  0  0  0
 23  1  1  0  0  0  0
 23  9  1  0  0  0  0
 24 10  1  0  0  0  0
 24 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047649

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COCC1=CC=C(O1)C1=C2NC3=CC=CC=C3C2=CC(=N1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H14N2O4/c1-23-9-10-6-7-15(24-10)17-16-12(8-14(20-17)18(21)22)11-4-2-3-5-13(11)19-16/h2-8,19H,9H2,1H3,(H,21,22)

> <INCHI_KEY>
DTVVELLZKPXBHH-UHFFFAOYSA-N

> <FORMULA>
C18H14N2O4

> <MOLECULAR_WEIGHT>
322.3148

> <EXACT_MASS>
322.095356946

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
34.325414803713684

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[5-(methoxymethyl)furan-2-yl]-9H-pyrido[3,4-b]indole-3-carboxylic acid

> <ALOGPS_LOGP>
3.23

> <JCHEM_LOGP>
2.8057466876666664

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.868772367209985

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.895036074921488

> <JCHEM_PKA_STRONGEST_BASIC>
0.2793821659274064

> <JCHEM_POLAR_SURFACE_AREA>
88.35

> <JCHEM_REFRACTIVITY>
86.7992

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.10e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[5-(methoxymethyl)furan-2-yl]-9H-pyrido[3,4-b]indole-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.303  10.265   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.917  -0.374   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.393   1.090   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.411  -0.695   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.362   2.235   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.083   5.715   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.083   4.175   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.810  -0.695   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.858   7.656   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.382   6.191   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.380   0.450   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.840   0.450   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.856   1.914   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.303  -0.374   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.382   3.699   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.364   1.914   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.858   2.235   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.727  -1.519   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       3.610   2.820   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0      -0.173   1.090   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0      -2.234  -1.199   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.251  -2.983   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.173   8.800   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       1.287   4.945   0.000  0.00  0.00           O+0
CONECT    1   23                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2   11                                                       
CONECT    5    3   13                                                       
CONECT    6    7   10                                                       
CONECT    7    6   15                                                       
CONECT    8   12   14                                                       
CONECT    9   10   23                                                       
CONECT   10    6    9   24                                                  
CONECT   11    4   12   13                                                  
CONECT   12    8   11   16                                                  
CONECT   13    5   11   19                                                  
CONECT   14    8   18   20                                                  
CONECT   15    7   17   24                                                  
CONECT   16   12   17   19                                                  
CONECT   17   15   16   20                                                  
CONECT   18   14   21   22                                                  
CONECT   19   13   16                                                       
CONECT   20   14   17                                                       
CONECT   21   18                                                            
CONECT   22   18                                                            
CONECT   23    1    9                                                       
CONECT   24   10   15                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Value	Source
2-(Diethylamino)ethyl 2,2-diphenylpentanoate	HMDB
2-(Diethylamino)ethyl 2,2-diphenylvalerate hydrochloride	HMDB
2-Diethylaminoethyl propyldiphenylacetate	HMDB
2-Diethylaminoethyl-2,2-diphenylvalerate	HMDB
Acetic acid, propyldiphenyl-, 2-(diethylamino)ethyl ester	HMDB
BCTB	HMDB
Diethylaminoethyldiphenylpropyl acetate	HMDB
Ethyl aprofen	HMDB
O-Methylflazine	HMDB
Proadifen	HMDB
Proadifene	HMDB
Proadifeno	HMDB
Proadifenum	HMDB
Propyladiphenin	HMDB
SKF-525a Hydrochloride	HMDB
Valeric acid, 2,2-diphenyl-, 2-(diethylamino)ethyl ester	HMDB
1-[5-(Methoxymethyl)furan-2-yl]-9H-pyrido[3,4-b]indole-3-carboxylate	Generator

Chemical Formula

C₁₈H₁₄N₂O₄

Average Mass

322.3148 Da

Monoisotopic Mass

322.09536 Da

IUPAC Name

1-[5-(methoxymethyl)furan-2-yl]-9H-pyrido[3,4-b]indole-3-carboxylic acid

Traditional Name

1-[5-(methoxymethyl)furan-2-yl]-9H-pyrido[3,4-b]indole-3-carboxylic acid

CAS Registry Number

159898-11-0

SMILES

COCC1=CC=C(O1)C1=C2NC3=CC=CC=C3C2=CC(=N1)C(O)=O

InChI Identifier

InChI=1S/C18H14N2O4/c1-23-9-10-6-7-15(24-10)17-16-12(8-14(20-17)18(21)22)11-4-2-3-5-13(11)19-16/h2-8,19H,9H2,1H3,(H,21,22)

InChI Key

DTVVELLZKPXBHH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ribes nigrum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Harmala alkaloids

Sub Class

Not Available

Direct Parent

Harmala alkaloids

Alternative Parents

Substituents

Harman
Beta-carboline
Pyridoindole
Indole
Indole or derivatives
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Benzenoid
Pyridine
Heteroaromatic compound
Furan
Pyrrole
Azacycle
Oxacycle
Dialkyl ether
Ether
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic oxide
Organic oxygen compound
Organopnictogen 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	3.23	ALOGPS
logP	2.81	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	3.9	ChemAxon
pKa (Strongest Basic)	0.28	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	88.35 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	86.8 m³·mol⁻¹	ChemAxon
Polarizability	34.33 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

HMDB ID

HMDB0033457

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011498

KNApSAcK ID

Not Available

Chemspider ID

30777003

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751427

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Flazine methyl ether (NP0047649)

MOL for NP0047649 (Flazine methyl ether)

3D MOL for NP0047649 (Flazine methyl ether)

3D SDF for NP0047649 (Flazine methyl ether)

3D-SDF for NP0047649 (Flazine methyl ether)

PDB for NP0047649 (Flazine methyl ether)

3D PDB for NP0047649 (Flazine methyl ether)

SMILES for NP0047649 (Flazine methyl ether)

INCHI for NP0047649 (Flazine methyl ether)

Structure for NP0047649 (Flazine methyl ether)

3D Structure for NP0047649 (Flazine methyl ether)