NP-MRD: Showing NP-Card for avicennone D (NP0032997)

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Record Information

Version

2.0

Created at

2021-06-19 23:39:45 UTC

Updated at

2021-06-30 00:02:31 UTC

NP-MRD ID

NP0032997

Secondary Accession Numbers

None

Natural Product Identification

Common Name

avicennone D

Provided By

JEOL Database JEOL Logo

Description

6-Hydroxy-4H,9H-naphtho[2,3-b]furan-4,9-dione 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. avicennone D is found in Avicennia marina. avicennone D was first documented in 2007 (Han, L., et al.). Based on a literature review very few articles have been published on 6-hydroxy-4H,9H-naphtho[2,3-b]furan-4,9-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101393D          

 22 24  0  0  0  0            999 V2000
    1.8614   -0.2889   -0.3110 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2647   -0.0849   -1.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1070    0.5147   -1.3695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7003    0.8410   -0.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9744    1.3992   -0.1267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5897    1.7320    1.0426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6681    1.6384   -1.3093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0859    1.3170   -2.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8036    0.7539   -2.5750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1969    0.4163   -3.9017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8131    0.6295   -4.9386 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1176   -0.1537   -3.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8360   -0.5273   -4.8991 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0170   -1.0185   -4.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0572   -0.9613   -3.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8221   -0.3991   -2.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1642    0.6570    0.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0053    1.5170    1.7894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6635    2.0757   -1.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6359    1.5076   -3.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7094   -1.3626   -5.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8724   -1.2834   -2.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0  0  0  0
 10 12  1  0  0  0  0
 16  2  1  0  0  0  0
 16 12  2  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  3  9  1  0  0  0  0
  7  8  1  0  0  0  0
 15 16  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  8  9  2  0  0  0  0
  2  1  2  0  0  0  0
  5  7  2  0  0  0  0
 10 11  2  0  0  0  0
  3  2  1  0  0  0  0
  5  6  1  0  0  0  0
  7 19  1  0  0  0  0
  8 20  1  0  0  0  0
  4 17  1  0  0  0  0
 15 22  1  0  0  0  0
 14 21  1  0  0  0  0
  6 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0032997

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C2C(=O)C3=C(C([H])=C([H])O3)C(=O)C2=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H6O4/c13-6-1-2-7-9(5-6)10(14)8-3-4-16-12(8)11(7)15/h1-5,13H

> <INCHI_KEY>
SKNZDXFIGIOJSJ-UHFFFAOYSA-N

> <FORMULA>
C12H6O4

> <MOLECULAR_WEIGHT>
214.176

> <EXACT_MASS>
214.026608673

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
20.356967036625008

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-hydroxy-4H,9H-naphtho[2,3-b]furan-4,9-dione

> <ALOGPS_LOGP>
2.56

> <JCHEM_LOGP>
1.6753873969999997

> <ALOGPS_LOGS>
-2.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.119983062930052

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1470550933995116

> <JCHEM_POLAR_SURFACE_AREA>
67.50999999999999

> <JCHEM_REFRACTIVITY>
55.5228

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.38e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxynaphtho[2,3-b]furan-4,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  O   UNK     0       1.861  -0.289  -0.311  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.265  -0.085  -1.360  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.107   0.515  -1.369  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.700   0.841  -0.141  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.974   1.399  -0.127  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.590   1.732   1.043  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.668   1.638  -1.309  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.086   1.317  -2.537  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.804   0.754  -2.575  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.197   0.416  -3.902  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.813   0.630  -4.939  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.118  -0.154  -3.808  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.836  -0.527  -4.899  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.017  -1.018  -4.431  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.057  -0.961  -3.054  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.822  -0.399  -2.653  0.00  0.00           C+0
HETATM   17  H   UNK     0      -0.164   0.657   0.787  0.00  0.00           H+0
HETATM   18  H   UNK     0      -2.005   1.517   1.789  0.00  0.00           H+0
HETATM   19  H   UNK     0      -3.664   2.076  -1.275  0.00  0.00           H+0
HETATM   20  H   UNK     0      -2.636   1.508  -3.457  0.00  0.00           H+0
HETATM   21  H   UNK     0       3.709  -1.363  -5.187  0.00  0.00           H+0
HETATM   22  H   UNK     0       3.872  -1.283  -2.420  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2   16    1    3                                                  
CONECT    3    4    9    2                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    7    6                                                  
CONECT    6    5   18                                                       
CONECT    7    8    5   19                                                  
CONECT    8    7    9   20                                                  
CONECT    9   10    3    8                                                  
CONECT   10    9   12   11                                                  
CONECT   11   10                                                            
CONECT   12   10   16   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   16   14   22                                                  
CONECT   16    2   12   15                                                  
CONECT   17    4                                                            
CONECT   18    6                                                            
CONECT   19    7                                                            
CONECT   20    8                                                            
CONECT   21   14                                                            
CONECT   22   15                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₆O₄

Average Mass

214.1760 Da

Monoisotopic Mass

214.02661 Da

IUPAC Name

6-hydroxy-4H,9H-naphtho[2,3-b]furan-4,9-dione

Traditional Name

6-hydroxynaphtho[2,3-b]furan-4,9-dione

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C2C(=O)C3=C(C([H])=C([H])O3)C(=O)C2=C1[H]

InChI Identifier

InChI=1S/C12H6O4/c13-6-1-2-7-9(5-6)10(14)8-3-4-16-12(8)11(7)15/h1-5,13H

InChI Key

SKNZDXFIGIOJSJ-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Avicennia marina	JEOL database	Han, L., et al, J. Nat. Prod. 70, 923 (2007)

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
Naphthalene
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Heteroaromatic compound
Furan
Ketone
Oxacycle
Organic oxygen compound
Organic oxide
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	2.56	ALOGPS
logP	1.68	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	7.12	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	67.51 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	55.52 m³·mol⁻¹	ChemAxon
Polarizability	20.36 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00038545

Chemspider ID

23283423

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44423352

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Han, L., et al. (2007). Han, L., et al, J. Nat. Prod. 70, 923 (2007). J. Nat. Prod..

Showing NP-Card for avicennone D (NP0032997)

MOL for NP0032997 (avicennone D)

3D MOL for NP0032997 (avicennone D)

3D SDF for NP0032997 (avicennone D)

3D-SDF for NP0032997 (avicennone D)

PDB for NP0032997 (avicennone D)

3D PDB for NP0032997 (avicennone D)

SMILES for NP0032997 (avicennone D)

INCHI for NP0032997 (avicennone D)

Structure for NP0032997 (avicennone D)

3D Structure for NP0032997 (avicennone D)