MiMeDB: Showing metabocard for 5,7-dihydroxy-2-[1-(4-methoxy-6-oxo-6H-pyran-2-yl)-2-phenylethylamino]-[1,4]naphthoquinone (MMDBc0009825)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 02:13:45 UTC

Update Date

2022-08-31 06:30:51 UTC

Metabolite ID

MMDBc0009825

Metabolite Identification

Common Name

5,7-dihydroxy-2-[1-(4-methoxy-6-oxo-6H-pyran-2-yl)-2-phenylethylamino]-[1,4]naphthoquinone

Description

5,7-dihydroxy-2-[1-(4-methoxy-6-oxo-6h-pyran-2-yl)-2-phenylethylamino]-[1,4]naphthoquinone belongs to the class of organic compounds known as kavalactones. These are lactones, which is structurally characterized by a benzene ring and a pyranone moiety, linked to each other to form a 4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one skeleton. Based on a literature review very few articles have been published on 5,7-dihydroxy-2-[1-(4-methoxy-6-oxo-6h-pyran-2-yl)-2-phenylethylamino]-[1,4]naphthoquinone.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152104132D          

 32 35  0  0  0  0            999 V2000
    6.4302    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 C   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
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 C   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
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    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
  6  4  2  0  0  0  0
 13  5  2  0  0  0  0
 13  6  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  2  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  2  0  0  0  0
 16  8  1  0  0  0  0
 17  7  1  0  0  0  0
 18 12  2  0  0  0  0
 19  9  2  0  0  0  0
 20 12  1  0  0  0  0
 21 10  2  0  0  0  0
 21 17  1  0  0  0  0
 22 11  1  0  0  0  0
 23 16  2  0  0  0  0
 23 19  1  0  0  0  0
 23 20  1  0  0  0  0
 24 16  1  0  0  0  0
 24 18  1  0  0  0  0
 25 17  1  0  0  0  0
 25 18  1  0  0  0  0
 26 14  1  0  0  0  0
 27 19  1  0  0  0  0
 28 20  2  0  0  0  0
 29 22  2  0  0  0  0
 30 24  2  0  0  0  0
 31  1  1  0  0  0  0
 31 15  1  0  0  0  0
 32 21  1  0  0  0  0
 32 22  1  0  0  0  0
M  END


  Mrv1652305152104132D          

 32 35  0  0  0  0            999 V2000
    6.4302    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 C   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
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 C   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
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    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
  6  4  2  0  0  0  0
 13  5  2  0  0  0  0
 13  6  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  2  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  2  0  0  0  0
 16  8  1  0  0  0  0
 17  7  1  0  0  0  0
 18 12  2  0  0  0  0
 19  9  2  0  0  0  0
 20 12  1  0  0  0  0
 21 10  2  0  0  0  0
 21 17  1  0  0  0  0
 22 11  1  0  0  0  0
 23 16  2  0  0  0  0
 23 19  1  0  0  0  0
 23 20  1  0  0  0  0
 24 16  1  0  0  0  0
 24 18  1  0  0  0  0
 25 17  1  0  0  0  0
 25 18  1  0  0  0  0
 26 14  1  0  0  0  0
 27 19  1  0  0  0  0
 28 20  2  0  0  0  0
 29 22  2  0  0  0  0
 30 24  2  0  0  0  0
 31  1  1  0  0  0  0
 31 15  1  0  0  0  0
 32 21  1  0  0  0  0
 32 22  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0009825

> <DATABASE_NAME>
MIME

> <SMILES>
COC1=CC(=O)OC(=C1)C(CC1=CC=CC=C1)NC1=CC(=O)C2=C(C=C(O)C=C2O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H19NO7/c1-31-15-10-21(32-22(29)11-15)17(7-13-5-3-2-4-6-13)25-18-12-20(28)23-16(24(18)30)8-14(26)9-19(23)27/h2-6,8-12,17,25-27H,7H2,1H3

> <INCHI_KEY>
SDOTUWDXEGNQEU-UHFFFAOYSA-N

> <FORMULA>
C24H19NO7

> <MOLECULAR_WEIGHT>
433.416

> <EXACT_MASS>
433.116151956

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
43.00697282463656

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-2-{[1-(4-methoxy-2-oxo-2H-pyran-6-yl)-2-phenylethyl]amino}-1,4-dihydronaphthalene-1,4-dione

> <ALOGPS_LOGP>
3.40

> <JCHEM_LOGP>
3.0204066419999993

> <ALOGPS_LOGS>
-4.88

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.971396024386667

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.364133963697919

> <JCHEM_PKA_STRONGEST_BASIC>
-4.825064032181144

> <JCHEM_POLAR_SURFACE_AREA>
122.16

> <JCHEM_REFRACTIVITY>
119.42279999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.69e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-2-{[1-(4-methoxy-6-oxopyran-2-yl)-2-phenylethyl]amino}naphthalene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0      12.003  11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  11.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002  10.780   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.003   8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669   9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.003   6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       8.002   4.620   0.000  0.00  0.00           N+0
HETATM   26  O   UNK     0      -0.000   4.620   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      13.337   6.160   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      10.669  10.780   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      10.669   6.160   0.000  0.00  0.00           O+0
CONECT    1   31                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3   13                                                       
CONECT    6    4   13                                                       
CONECT    7   13   17                                                       
CONECT    8   14   16                                                       
CONECT    9   14   19                                                       
CONECT   10   15   21                                                       
CONECT   11   15   22                                                       
CONECT   12   18   20                                                       
CONECT   13    5    6    7                                                  
CONECT   14    8    9   26                                                  
CONECT   15   10   11   31                                                  
CONECT   16    8   23   24                                                  
CONECT   17    7   21   25                                                  
CONECT   18   12   24   25                                                  
CONECT   19    9   23   27                                                  
CONECT   20   12   23   28                                                  
CONECT   21   10   17   32                                                  
CONECT   22   11   29   32                                                  
CONECT   23   16   19   20                                                  
CONECT   24   16   18   30                                                  
CONECT   25   17   18                                                       
CONECT   26   14                                                            
CONECT   27   19                                                            
CONECT   28   20                                                            
CONECT   29   22                                                            
CONECT   30   24                                                            
CONECT   31    1   15                                                       
CONECT   32   21   22                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

Synonyms

Not Available

Molecular Formula

C₂₄H₁₉NO₇

Average Mass

433.416

Monoisotopic Mass

433.116151956

IUPAC Name

5,7-dihydroxy-2-{[1-(4-methoxy-2-oxo-2H-pyran-6-yl)-2-phenylethyl]amino}-1,4-dihydronaphthalene-1,4-dione

Traditional Name

5,7-dihydroxy-2-{[1-(4-methoxy-6-oxopyran-2-yl)-2-phenylethyl]amino}naphthalene-1,4-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)OC(=C1)C(CC1=CC=CC=C1)NC1=CC(=O)C2=C(C=C(O)C=C2O)C1=O

InChI Identifier

InChI=1S/C24H19NO7/c1-31-15-10-21(32-22(29)11-15)17(7-13-5-3-2-4-6-13)25-18-12-20(28)23-16(24(18)30)8-14(26)9-19(23)27/h2-6,8-12,17,25-27H,7H2,1H3

InChI Key

SDOTUWDXEGNQEU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kavalactones. These are lactones, which is structurally characterized by a benzene ring and a pyranone moiety, linked to each other to form a 4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Kavalactones

Sub Class

Not Available

Direct Parent

Kavalactones

Alternative Parents

Substituents

Kavalactone
Naphthoquinone
Amphetamine or derivatives
Naphthalene
Quinone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
Aralkylamine
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous ester
Vinylogous amide
Vinylogous acid
Ketone
Lactone
Secondary aliphatic amine
Enamine
Ether
Oxacycle
Organoheterocyclic compound
Secondary amine
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Amine
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0057 g/L	ALOGPS
logP	3.4	ALOGPS
logP	3.02	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	7.36	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.16 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	119.42 m³·mol⁻¹	ChemAxon
Polarizability	43.01 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	Yes	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

23076507

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

132426871

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for 5,7-dihydroxy-2-[1-(4-methoxy-6-oxo-6H-pyran-2-yl)-2-phenylethylamino]-[1,4]naphthoquinone (MMDBc0009825)

MOL for #<Metabolite:0x00007f9239076bb0>

3D MOL for #<Metabolite:0x00007f9239076bb0>

3D SDF for #<Metabolite:0x00007f9239076bb0>

3D-SDF for #<Metabolite:0x00007f9239076bb0>

PDB for #<Metabolite:0x00007f9239076bb0>

3D PDB for #<Metabolite:0x00007f9239076bb0>

SMILES for #<Metabolite:0x00007f9239076bb0>

INCHI for #<Metabolite:0x00007f9239076bb0>

Structure for #<Metabolite:0x00007f9239076bb0>

3D Structure for #<Metabolite:0x00007f9239076bb0>