NP-MRD: Showing NP-Card for 5,6-dihydroxy-1-(indol-3-ylidene)naphtho[2,1-b]furan-2-one (NP0220746)

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Record Information

Version

2.0

Created at

2022-09-05 22:08:50 UTC

Updated at

2022-09-05 22:08:50 UTC

NP-MRD ID

NP0220746

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,6-dihydroxy-1-(indol-3-ylidene)naphtho[2,1-b]furan-2-one

Description

Exophialin belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. 5,6-dihydroxy-1-(indol-3-ylidene)naphtho[2,1-b]furan-2-one is found in Exophiala dermatitidis. Based on a literature review very few articles have been published on Exophialin.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062200082D          

 25 29  0  0  0  0            999 V2000
    4.2380   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4130   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280   -1.4924    0.0000 O   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
    1.4289   -1.6500    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
   -0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280   -0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830    0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6981    1.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830    1.9619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9676    1.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6821    2.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3965    1.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3965    0.8820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6821    0.4695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9676    0.8820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
  4 15  1  0  0  0  0
 16 15  1  4  0  0  0
  2 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 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 17 25  1  0  0  0  0
M  END


  Mrv1652309062200082D          

 25 29  0  0  0  0            999 V2000
    4.2380   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4130   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280   -1.4924    0.0000 O   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
    1.4289   -1.6500    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
   -0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280   -0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830    0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6981    1.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830    1.9619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9676    1.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6821    2.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3965    1.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3965    0.8820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6821    0.4695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9676    0.8820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
  4 15  1  0  0  0  0
 16 15  1  4  0  0  0
  2 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 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 17 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0220746

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=CC2=C3C(OC(=O)C3=C3C=NC4=CC=CC=C34)=CC(O)=C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H11NO4/c22-14-7-3-5-11-17(14)15(23)8-16-18(11)19(20(24)25-16)12-9-21-13-6-2-1-4-10(12)13/h1-9,22-23H

> <INCHI_KEY>
VGIZKLWKWLGUOS-UHFFFAOYSA-N

> <FORMULA>
C20H11NO4

> <MOLECULAR_WEIGHT>
329.311

> <EXACT_MASS>
329.068807838

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
34.14584255197407

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,6-dihydroxy-1-(3H-indol-3-ylidene)-1H,2H-naphtho[2,1-b]furan-2-one

> <JCHEM_LOGP>
3.771443894333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.808048283961043

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.758139928131164

> <JCHEM_PKA_STRONGEST_BASIC>
0.5209595013001785

> <JCHEM_POLAR_SURFACE_AREA>
79.12000000000002

> <JCHEM_REFRACTIVITY>
94.1741

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5,6-dihydroxy-1-(indol-3-ylidene)naphtho[2,1-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  O   UNK     0       7.911  -1.540   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.371  -1.540   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.466  -2.786   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.466  -0.294   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.942   1.171   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.036   2.416   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       5.942   3.662   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       7.406   3.186   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.740   3.956   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.074   3.186   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.074   1.646   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.740   0.876   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.406   1.646   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   15                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14    4   16                                                  
CONECT   16   15    2   17                                                  
CONECT   17   16   18   25                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20   17                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₁NO₄

Average Mass

329.3110 Da

Monoisotopic Mass

329.06881 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OC1=CC=CC2=C3C(OC(=O)C3=C3C=NC4=CC=CC=C34)=CC(O)=C12

InChI Identifier

InChI=1S/C20H11NO4/c22-14-7-3-5-11-17(14)15(23)8-16-18(11)19(20(24)25-16)12-9-21-13-6-2-1-4-10(12)13/h1-9,22-23H

InChI Key

VGIZKLWKWLGUOS-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Exophiala dermatitidis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
1-naphthol
Naphthalene
Coumaran
Indole or derivatives
Benzofuran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Carboxylic acid ester
Oxacycle
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Carbonyl group
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78434965

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

136750314

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5,6-dihydroxy-1-(indol-3-ylidene)naphtho[2,1-b]furan-2-one (NP0220746)

MOL for NP0220746 (5,6-dihydroxy-1-(indol-3-ylidene)naphtho[2,1-b]furan-2-one)

3D MOL for NP0220746 (5,6-dihydroxy-1-(indol-3-ylidene)naphtho[2,1-b]furan-2-one)

3D SDF for NP0220746 (5,6-dihydroxy-1-(indol-3-ylidene)naphtho[2,1-b]furan-2-one)

3D-SDF for NP0220746 (5,6-dihydroxy-1-(indol-3-ylidene)naphtho[2,1-b]furan-2-one)

PDB for NP0220746 (5,6-dihydroxy-1-(indol-3-ylidene)naphtho[2,1-b]furan-2-one)

3D PDB for NP0220746 (5,6-dihydroxy-1-(indol-3-ylidene)naphtho[2,1-b]furan-2-one)

SMILES for NP0220746 (5,6-dihydroxy-1-(indol-3-ylidene)naphtho[2,1-b]furan-2-one)

INCHI for NP0220746 (5,6-dihydroxy-1-(indol-3-ylidene)naphtho[2,1-b]furan-2-one)

Structure for NP0220746 (5,6-dihydroxy-1-(indol-3-ylidene)naphtho[2,1-b]furan-2-one)

3D Structure for NP0220746 (5,6-dihydroxy-1-(indol-3-ylidene)naphtho[2,1-b]furan-2-one)