NP-MRD: Showing NP-Card for Acetyl-N-formyl-5-methoxykynurenamine (NP0087168)

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Record Information

Version

2.0

Created at

2022-05-11 16:42:02 UTC

Updated at

2022-05-11 16:42:02 UTC

NP-MRD ID

NP0087168

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Acetyl-N-formyl-5-methoxykynurenamine

Description

Acetyl-N-formyl-5-methoxykynurenamine, also known as AFMK or NSC 688263, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Acetyl-N-formyl-5-methoxykynurenamine is an extremely weak basic (essentially neutral) compound (based on its pKa). Acetyl-N-formyl-5-methoxykynurenamine exists in all living organisms, ranging from bacteria to humans. Acetyl-N-formyl-5-methoxykynurenamine can be biosynthesized from melatonin through the action of the enzyme indoleamine 2,3-dioxygenase 1. Acetyl-N-formyl-5-methoxykynurenamine was first documented in 2005 (PMID: 16150112). In humans, acetyl-N-formyl-5-methoxykynurenamine is involved in tryptophan metabolism.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 35  0  0  0  0  0  0  0  0999 V2000
    1.4166    3.0797    1.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5503    2.2482    1.6778 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4822    0.9548    1.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5704    0.1308    1.2695 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4908   -1.1661    0.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2804   -1.6389    0.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1906   -2.9944   -0.1820 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2814   -3.8487   -0.4580 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4633   -3.5057   -0.3704 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1751   -0.8328    0.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0869   -1.2097   -0.4486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2778   -2.3274   -0.9868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1954   -0.2141   -0.4284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4072   -0.7365   -1.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3740    0.1624   -1.2006 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4132    1.1287   -1.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2146    2.3812   -0.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4865    1.0471   -1.7387 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3202    0.4750    0.6621 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0525    3.0754    0.5353 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8207    4.1357    1.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6204    2.8519    2.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5276    0.4730    1.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3509   -1.8092    0.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2470   -3.4442   -0.2749 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0579   -4.8761   -0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8312    0.7191   -0.8585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5413   -0.0988    0.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6834   -1.7247   -0.7483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0120   -1.0791   -2.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1485   -0.5988   -2.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5762    3.2293   -0.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9055    2.3432    0.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1843    2.5408   -0.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4401    1.1289    0.6030 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 19  2  0
 19 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 10  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 19 35  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
  7 25  1  0
  8 26  1  0
  5 24  1  0
  4 23  1  0
M  END


  Mrv1652301231818222D          

 19 19  0  0  0  0            999 V2000
10000.839710002.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.553610001.5993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.266010002.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.980410001.5993    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10003.692810002.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.405110001.5993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.692810002.8368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.839710002.8368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.415510002.8368    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.702310003.2465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.989110002.8368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.4155 9999.5426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6982 9999.1277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.128710001.6011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.414210002.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.699510001.6011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.699510000.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.414110000.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.128810000.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 13  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 14  1  0  0  0  0
 18 12  1  0  0  0  0
 15  9  1  0  0  0  0
  1 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0087168

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(C(=O)CCNC(C)=O)=C(NC=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H16N2O4/c1-9(17)14-6-5-13(18)11-7-10(19-2)3-4-12(11)15-8-16/h3-4,7-8H,5-6H2,1-2H3,(H,14,17)(H,15,16)

> <INCHI_KEY>
JYWNYMJKURVPFH-UHFFFAOYSA-N

> <FORMULA>
C13H16N2O4

> <MOLECULAR_WEIGHT>
264.2771

> <EXACT_MASS>
264.11100701

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.128527652920056

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[3-(2-formamido-5-methoxyphenyl)-3-oxopropyl]acetamide

> <ALOGPS_LOGP>
0.50

> <JCHEM_LOGP>
0.34396322500000004

> <ALOGPS_LOGS>
-3.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.91444802762295

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.901185222069476

> <JCHEM_PKA_STRONGEST_BASIC>
-1.571848798118829

> <JCHEM_POLAR_SURFACE_AREA>
84.5

> <JCHEM_REFRACTIVITY>
70.79940000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.69e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[3-(2-formamido-5-methoxyphenyl)-3-oxopropyl]acetamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-JAN-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-JAN-18         0                                  
HETATM    1  C   UNK     0    8668.2348670.425   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8669.5678669.652   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8670.8978670.425   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0    8672.2308669.652   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0    8673.5608670.425   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8674.8898669.652   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8673.5608671.962   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8668.2348671.962   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0    8665.5768671.962   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0    8664.2448672.727   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8662.9138671.962   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8665.5768665.813   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    8664.2378665.038   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8666.9078669.655   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8665.5738670.426   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8664.2398669.655   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8664.2398668.115   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8665.5738667.345   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8666.9078668.115   0.000  0.00  0.00           C+0
CONECT    1    2    8   14                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    1                                                            
CONECT    9   10   15                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12   13   18                                                       
CONECT   13   12                                                            
CONECT   14   15   19    1                                                  
CONECT   15   14   16    9                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   12                                                  
CONECT   19   18   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
N-Acetyl-N-formyl-5-methoxykynurenamine	HMDB
AFMK	HMDB
Formyl-N-acetyl-5-methoxykynurenamine	HMDB
N-[3-(2-Formamido-5-methoxy-phenyl)-3-oxo-propyl]acetamide	HMDB
N1-Acetyl-N2-formyl-5-methoxykynurenine	HMDB
NSC 688263	HMDB
K1	HMDB

Chemical Formula

C₁₃H₁₆N₂O₄

Average Mass

264.2771 Da

Monoisotopic Mass

264.11101 Da

IUPAC Name

N-[3-(2-formamido-5-methoxyphenyl)-3-oxopropyl]acetamide

Traditional Name

N-[3-(2-formamido-5-methoxyphenyl)-3-oxopropyl]acetamide

CAS Registry Number

Not Available

SMILES

COC1=CC(C(=O)CCNC(C)=O)=C(NC=O)C=C1

InChI Identifier

InChI=1S/C13H16N2O4/c1-9(17)14-6-5-13(18)11-7-10(19-2)3-4-12(11)15-8-16/h3-4,7-8H,5-6H2,1-2H3,(H,14,17)(H,15,16)

InChI Key

JYWNYMJKURVPFH-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Methoxyaniline
Anilide
Phenoxy compound
Anisole
Benzoyl
Phenol ether
Methoxybenzene
N-arylamide
Aryl alkyl ketone
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Acetamide
Vinylogous amide
Secondary carboxylic acid amide
Carboxamide group
Ether
Carboxylic acid derivative
Hydrocarbon derivative
Organonitrogen compound
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

kynurenamines (CHEBI:28613 )
a small molecule (CPD-12022 )

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	0.5	ALOGPS
logP	0.34	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	13.9	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	84.5 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	70.8 m³·mol⁻¹	ChemAxon
Polarizability	27.13 Å³	ChemAxon
Number of Rings	1	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

HMDB0004259

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023355

KNApSAcK ID

Not Available

Chemspider ID

149637

KEGG Compound ID

C05642

BioCyc ID

Not Available

BiGG ID

46183

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

171161

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Silva SO, Ximenes VF, Livramento JA, Catalani LH, Campa A: High concentrations of the melatonin metabolite, N1-acetyl-N2-formyl-5-methoxykynuramine, in cerebrospinal fluid of patients with meningitis: a possible immunomodulatory mechanism. J Pineal Res. 2005 Oct;39(3):302-6. doi: 10.1111/j.1600-079X.2005.00247.x. [PubMed:16150112 ]

Showing NP-Card for Acetyl-N-formyl-5-methoxykynurenamine (NP0087168)

MOL for NP0087168 (Acetyl-N-formyl-5-methoxykynurenamine)

3D MOL for NP0087168 (Acetyl-N-formyl-5-methoxykynurenamine)

3D SDF for NP0087168 (Acetyl-N-formyl-5-methoxykynurenamine)

3D-SDF for NP0087168 (Acetyl-N-formyl-5-methoxykynurenamine)

PDB for NP0087168 (Acetyl-N-formyl-5-methoxykynurenamine)

3D PDB for NP0087168 (Acetyl-N-formyl-5-methoxykynurenamine)

SMILES for NP0087168 (Acetyl-N-formyl-5-methoxykynurenamine)

INCHI for NP0087168 (Acetyl-N-formyl-5-methoxykynurenamine)

Structure for NP0087168 (Acetyl-N-formyl-5-methoxykynurenamine)

3D Structure for NP0087168 (Acetyl-N-formyl-5-methoxykynurenamine)