MiMeDB: Showing metabocard for nor-toralactone (MMDBc0056225)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 20:20:00 UTC

Update Date

2022-08-12 20:09:38 UTC

Metabolite ID

MMDBc0056225

Metabolite Identification

Common Name

nor-toralactone

Description

3-Methyl-7,9,10-trihydroxy-1H-naphtho[2,3-c]pyran-1-one belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. 3-Methyl-7,9,10-trihydroxy-1H-naphtho[2,3-c]pyran-1-one is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on 3-Methyl-7,9,10-trihydroxy-1H-naphtho[2,3-c]pyran-1-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172222202D          

 19 21  0  0  0  0            999 V2000
    0.7145   -1.2375    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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    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
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   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
  6  1  1  0  0  0  0
  6  2  2  0  0  0  0
  7  2  1  0  0  0  0
  7  3  2  0  0  0  0
  8  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  4  1  0  0  0  0
  9  5  2  0  0  0  0
 10  5  1  0  0  0  0
 11  8  1  0  0  0  0
 11 10  2  0  0  0  0
 12  7  1  0  0  0  0
 13 11  1  0  0  0  0
 13 12  2  0  0  0  0
 14 12  1  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17 13  1  0  0  0  0
 18 14  2  0  0  0  0
 19  6  1  0  0  0  0
 19 14  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0056225

> <DATABASE_NAME>
MIME

> <SMILES>
CC1=CC2=CC3=CC(O)=CC(O)=C3C(O)=C2C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C14H10O5/c1-6-2-7-3-8-4-9(15)5-10(16)11(8)13(17)12(7)14(18)19-6/h2-5,15-17H,1H3

> <INCHI_KEY>
CHFXJVIAQRGNOY-UHFFFAOYSA-N

> <FORMULA>
C14H10O5

> <MOLECULAR_WEIGHT>
258.229

> <EXACT_MASS>
258.052823422

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
25.369366365482254

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7,9,10-trihydroxy-3-methyl-1H-benzo[g]isochromen-1-one

> <JCHEM_LOGP>
2.984243833

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.441059946633064

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.432823085807717

> <JCHEM_PKA_STRONGEST_BASIC>
-4.482573556873565

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
69.69800000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
7,9,10-trihydroxy-3-methylbenzo[g]isochromen-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    6    7                                                       
CONECT    3    7    8                                                       
CONECT    4    8    9                                                       
CONECT    5    9   10                                                       
CONECT    6    1    2   19                                                  
CONECT    7    2    3   12                                                  
CONECT    8    3    4   11                                                  
CONECT    9    4    5   15                                                  
CONECT   10    5   11   16                                                  
CONECT   11    8   10   13                                                  
CONECT   12    7   13   14                                                  
CONECT   13   11   12   17                                                  
CONECT   14   12   18   19                                                  
CONECT   15    9                                                            
CONECT   16   10                                                            
CONECT   17   13                                                            
CONECT   18   14                                                            
CONECT   19    6   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

Synonyms

Value	Source
7,9,10-Trihydroxy-3-methyl-1H-naphtho[2,3-c]pyran-1-one	ChEBI

Molecular Formula

C₁₄H₁₀O₅

Average Mass

258.229

Monoisotopic Mass

258.052823422

IUPAC Name

7,9,10-trihydroxy-3-methyl-1H-benzo[g]isochromen-1-one

Traditional Name

7,9,10-trihydroxy-3-methylbenzo[g]isochromen-1-one

CAS Registry Number

Not Available

SMILES

CC1=CC2=CC3=CC(O)=CC(O)=C3C(O)=C2C(=O)O1

InChI Identifier

InChI=1S/C14H10O5/c1-6-2-7-3-8-4-9(15)5-10(16)11(8)13(17)12(7)14(18)19-6/h2-5,15-17H,1H3

InChI Key

CHFXJVIAQRGNOY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Substituents

Naphthopyranone
Isocoumarin
2-naphthol
1-naphthol
Benzopyran
Naphthalene
2-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Lactone
Polyol
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen 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
logP	2.98	ChemAxon
pKa (Strongest Acidic)	8.43	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.7 m³·mol⁻¹	ChemAxon
Polarizability	25.37 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

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	3

Exposure Sources

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

8054003

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9878326

PDB ID

Not Available

ChEBI ID

146018

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for nor-toralactone (MMDBc0056225)

MOL for #<Metabolite:0x00007fdb2f0d88a8>

3D MOL for #<Metabolite:0x00007fdb2f0d88a8>

3D SDF for #<Metabolite:0x00007fdb2f0d88a8>

3D-SDF for #<Metabolite:0x00007fdb2f0d88a8>

PDB for #<Metabolite:0x00007fdb2f0d88a8>

3D PDB for #<Metabolite:0x00007fdb2f0d88a8>

SMILES for #<Metabolite:0x00007fdb2f0d88a8>

INCHI for #<Metabolite:0x00007fdb2f0d88a8>

Structure for #<Metabolite:0x00007fdb2f0d88a8>

3D Structure for #<Metabolite:0x00007fdb2f0d88a8>