NP-MRD: Showing NP-Card for Flazine (NP0047650)

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Record Information

Version

2.0

Created at

2022-03-17 20:43:41 UTC

Updated at

2022-03-17 20:43:41 UTC

NP-MRD ID

NP0047650

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Flazine

Description

Flazine 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 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Flazine has been detected, but not quantified in, a few different foods, such as beverages, herbs and spices, and soy beans. Flazine is found in Brucea javanica and Ophiocordyceps sinensis. This could make flazine a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307082D          

 23 26  0  0  0  0            999 V2000
    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
   -0.0925    4.7143    0.0000 O   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
    0.6895    2.6492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  0  0  0  0
  9  5  2  0  0  0  0
  9  8  1  0  0  0  0
 10  3  2  0  0  0  0
 11  7  2  0  0  0  0
 11 10  1  0  0  0  0
 12  4  2  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 14  6  2  0  0  0  0
 15 11  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  2  0  0  0  0
 17 13  1  0  0  0  0
 18 12  1  0  0  0  0
 18 15  1  0  0  0  0
 19 13  2  0  0  0  0
 19 16  1  0  0  0  0
 20  8  1  0  0  0  0
 21 17  1  0  0  0  0
 22 17  2  0  0  0  0
 23  9  1  0  0  0  0
 23 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047650

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1=CC=C(O1)C1=C2NC3=CC=CC=C3C2=CC(=N1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H12N2O4/c20-8-9-5-6-14(23-9)16-15-11(7-13(19-16)17(21)22)10-3-1-2-4-12(10)18-15/h1-7,18,20H,8H2,(H,21,22)

> <INCHI_KEY>
USBWYUYKHHILLZ-UHFFFAOYSA-N

> <FORMULA>
C17H12N2O4

> <MOLECULAR_WEIGHT>
308.2882

> <EXACT_MASS>
308.079706882

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
32.08935918608638

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.64

> <JCHEM_LOGP>
2.1626201839999997

> <ALOGPS_LOGS>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.810302584183646

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.895044051693421

> <JCHEM_PKA_STRONGEST_BASIC>
0.27944288769682946

> <JCHEM_POLAR_SURFACE_AREA>
99.35000000000001

> <JCHEM_REFRACTIVITY>
82.04799999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[5-(hydroxymethyl)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       6.917  -0.374   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.393   1.090   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.411  -0.695   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.362   2.235   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.083   5.715   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.083   4.175   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.810  -0.695   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.858   7.656   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.382   6.191   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.380   0.450   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.840   0.450   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.856   1.914   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.303  -0.374   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.382   3.699   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.364   1.914   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.858   2.235   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.727  -1.519   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       3.610   2.820   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0      -0.173   1.090   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0      -0.173   8.800   0.000  0.00  0.00           O+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       1.287   4.945   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1   10                                                       
CONECT    4    2   12                                                       
CONECT    5    6    9                                                       
CONECT    6    5   14                                                       
CONECT    7   11   13                                                       
CONECT    8    9   20                                                       
CONECT    9    5    8   23                                                  
CONECT   10    3   11   12                                                  
CONECT   11    7   10   15                                                  
CONECT   12    4   10   18                                                  
CONECT   13    7   17   19                                                  
CONECT   14    6   16   23                                                  
CONECT   15   11   16   18                                                  
CONECT   16   14   15   19                                                  
CONECT   17   13   21   22                                                  
CONECT   18   12   15                                                       
CONECT   19   13   16                                                       
CONECT   20    8                                                            
CONECT   21   17                                                            
CONECT   22   17                                                            
CONECT   23    9   14                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Value	Source
1-[5-(Hydroxymethyl)-2-furanyl]-9H-pyrido[3,4-b]indole-3-carboxylic acid, 9ci	HMDB
Flazin	HMDB
1-[5-(Hydroxymethyl)furan-2-yl]-9H-pyrido[3,4-b]indole-3-carboxylate	Generator
Flazine	MeSH

Chemical Formula

C₁₇H₁₂N₂O₄

Average Mass

308.2882 Da

Monoisotopic Mass

308.07971 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

100041-05-2

SMILES

OCC1=CC=C(O1)C1=C2NC3=CC=CC=C3C2=CC(=N1)C(O)=O

InChI Identifier

InChI=1S/C17H12N2O4/c20-8-9-5-6-14(23-9)16-15-11(7-13(19-16)17(21)22)10-3-1-2-4-12(10)18-15/h1-7,18,20H,8H2,(H,21,22)

InChI Key

USBWYUYKHHILLZ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Brucea javanica	LOTUS Database	35616633
Glycine max	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ophiocordyceps sinensis	LOTUS Database	35616633

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
Pyrrole
Furan
Azacycle
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organonitrogen compound
Organooxygen compound
Alcohol
Organic oxygen compound
Primary alcohol
Organic nitrogen compound
Organopnictogen compound
Aromatic alcohol
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

harmala alkaloid (CHEBI:69443 )

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	2.64	ALOGPS
logP	2.16	ChemAxon
logS	-3.4	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	3	ChemAxon
Polar Surface Area	99.35 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	82.05 m³·mol⁻¹	ChemAxon
Polarizability	32.09 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

HMDB0033459

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011500

KNApSAcK ID

Not Available

Chemspider ID

4526683

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5377686

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Flazine (NP0047650)

MOL for NP0047650 (Flazine)

3D MOL for NP0047650 (Flazine)

3D SDF for NP0047650 (Flazine)

3D-SDF for NP0047650 (Flazine)

PDB for NP0047650 (Flazine)

3D PDB for NP0047650 (Flazine)

SMILES for NP0047650 (Flazine)

INCHI for NP0047650 (Flazine)

Structure for NP0047650 (Flazine)

3D Structure for NP0047650 (Flazine)