NP-MRD: Showing NP-Card for FR198248 (NP0003673)

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Record Information

Version

2.0

Created at

2020-12-09 00:51:42 UTC

Updated at

2021-07-15 16:47:04 UTC

NP-MRD ID

NP0003673

Secondary Accession Numbers

None

Natural Product Identification

Common Name

FR198248

Provided By

NPAtlas

Description

FR198248 is found in Aspergillus and Aspergillus flavipes. FR198248 was first documented in 2001 (PMID: 11372786). Based on a literature review very few articles have been published on 4-methyl-1,3-dihydro-2-benzofuran-1,5,6,7-tetrol (PMID: 20139618).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117493D          

 24 25  0  0  0  0            999 V2000
    1.5423   -2.1534    0.3829 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9320   -0.8475    0.1016 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7276    0.2116   -0.2771 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0974    0.0581   -0.3954 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1352    1.4374   -0.5390 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9165    2.5110   -0.9199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2264    1.5837   -0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8334    2.8282   -0.6849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9884    0.5038   -0.0393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4395   -0.7313    0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5441   -1.6488    0.6067 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5496   -0.7718    0.9985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4509    0.3478    0.1734 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9082    1.4975    0.8089 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4384   -2.0745    1.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8474   -2.6846   -0.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8377   -2.8254    0.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4903   -0.8483   -0.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9038    2.3919   -1.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2456    3.6009   -0.9620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8426   -2.2394   -0.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2698   -2.3095    1.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9436    0.2090   -0.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6262    1.9539    0.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10  2  1  0  0  0  0
 13  9  1  0  0  0  0
  1 15  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  4 18  1  0  0  0  0
  6 19  1  0  0  0  0
  8 20  1  0  0  0  0
 11 21  1  0  0  0  0
 11 22  1  0  0  0  0
 13 23  1  6  0  0  0
 14 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003673

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(O[H])C(O[H])=C(C2=C1[C@]([H])(O[H])OC2([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O5/c1-3-4-2-14-9(13)5(4)7(11)8(12)6(3)10/h9-13H,2H2,1H3/t9-/m1/s1

> <INCHI_KEY>
GSKYCPXSDLXGEW-UHFFFAOYSA-N

> <FORMULA>
C9H10O5

> <MOLECULAR_WEIGHT>
198.174

> <EXACT_MASS>
198.052823422

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
18.734955752343787

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R)-4-methyl-1,3-dihydro-2-benzofuran-1,5,6,7-tetrol

> <ALOGPS_LOGP>
-0.26

> <JCHEM_LOGP>
0.8387513363333332

> <ALOGPS_LOGS>
-1.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.345817373250746

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.838749588114919

> <JCHEM_PKA_STRONGEST_BASIC>
-4.377408681477938

> <JCHEM_POLAR_SURFACE_AREA>
90.15

> <JCHEM_REFRACTIVITY>
48.19350000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.45e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R)-4-methyl-1,3-dihydro-2-benzofuran-1,5,6,7-tetrol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       1.542  -2.153   0.383  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.932  -0.848   0.102  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.728   0.212  -0.277  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.097   0.058  -0.395  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.135   1.437  -0.539  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.917   2.511  -0.920  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.226   1.584  -0.420  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.833   2.828  -0.685  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.988   0.504  -0.039  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.440  -0.731   0.230  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.544  -1.649   0.607  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.550  -0.772   0.999  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.451   0.348   0.173  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.908   1.498   0.809  0.00  0.00           O+0
HETATM   15  H   UNK     0       2.438  -2.075   1.049  0.00  0.00           H+0
HETATM   16  H   UNK     0       1.847  -2.685  -0.545  0.00  0.00           H+0
HETATM   17  H   UNK     0       0.838  -2.825   0.927  0.00  0.00           H+0
HETATM   18  H   UNK     0       3.490  -0.848  -0.197  0.00  0.00           H+0
HETATM   19  H   UNK     0       2.904   2.392  -1.003  0.00  0.00           H+0
HETATM   20  H   UNK     0      -0.246   3.601  -0.962  0.00  0.00           H+0
HETATM   21  H   UNK     0      -1.843  -2.239  -0.276  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.270  -2.309   1.450  0.00  0.00           H+0
HETATM   23  H   UNK     0      -2.944   0.209  -0.802  0.00  0.00           H+0
HETATM   24  H   UNK     0      -3.626   1.954   0.331  0.00  0.00           H+0
CONECT    1    2   15   16   17                                             
CONECT    2    1    3   10                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3   18                                                       
CONECT    5    3    6    7                                                  
CONECT    6    5   19                                                       
CONECT    7    5    8    9                                                  
CONECT    8    7   20                                                       
CONECT    9    7   10   13                                                  
CONECT   10    9   11    2                                                  
CONECT   11   10   12   21   22                                             
CONECT   12   11   13                                                       
CONECT   13   12   14    9   23                                             
CONECT   14   13   24                                                       
CONECT   15    1                                                            
CONECT   16    1                                                            
CONECT   17    1                                                            
CONECT   18    4                                                            
CONECT   19    6                                                            
CONECT   20    8                                                            
CONECT   21   11                                                            
CONECT   22   11                                                            
CONECT   23   13                                                            
CONECT   24   14                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₉H₁₀O₅

Average Mass

198.1740 Da

Monoisotopic Mass

198.05282 Da

IUPAC Name

(1R)-4-methyl-1,3-dihydro-2-benzofuran-1,5,6,7-tetrol

Traditional Name

(1R)-4-methyl-1,3-dihydro-2-benzofuran-1,5,6,7-tetrol

CAS Registry Number

Not Available

SMILES

CC1=C(O)C(O)=C(O)C2=C1COC2O

InChI Identifier

InChI=1S/C9H10O5/c1-3-4-2-14-9(13)5(4)7(11)8(12)6(3)10/h9-13H,2H2,1H3

InChI Key

GSKYCPXSDLXGEW-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
Aspergillus	NPAtlas	11372786
Aspergillus flavipes	LOTUS Database	35616633

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as isocoumarans. These are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 1,3-dihydrofuran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isocoumarans

Sub Class

Not Available

Direct Parent

Isocoumarans

Alternative Parents

Substituents

Isocoumaran
Benzenoid
Hemiacetal
Oxacycle
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen 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	-0.26	ALOGPS
logP	0.84	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	8.84	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	90.15 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	48.19 m³·mol⁻¹	ChemAxon
Polarizability	18.73 Å³	ChemAxon
Number of Rings	2	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

NPAtlas ID

NPA005390

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

7991315

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nishihara Y, Takase S, Tsujii E, Hatanaka H, Hashimoto S: New anti-influenza agents, FR198248 and its derivatives. II. Characterization of FR198248, its related compounds and some derivatives. J Antibiot (Tokyo). 2001 Mar;54(3):297-303. doi: 10.7164/antibiotics.54.297. [PubMed:11372786 ]
Kwon YJ, Zheng CJ, Kim WG: Isolation and identification of FR198248, a hydroxylated 1,3-dihydroisobenzofuran, from Aspergillus flavipes as an inhibitor of peptide deformylase. Biosci Biotechnol Biochem. 2010;74(2):390-3. doi: 10.1271/bbb.90565. Epub 2010 Feb 7. [PubMed:20139618 ]

Showing NP-Card for FR198248 (NP0003673)

MOL for NP0003673 (FR198248)

3D MOL for NP0003673 (FR198248)

3D SDF for NP0003673 (FR198248)

3D-SDF for NP0003673 (FR198248)

PDB for NP0003673 (FR198248)

3D PDB for NP0003673 (FR198248)

SMILES for NP0003673 (FR198248)

INCHI for NP0003673 (FR198248)

Structure for NP0003673 (FR198248)

3D Structure for NP0003673 (FR198248)