NP-MRD: Showing NP-Card for saccharonol A (NP0042667)

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Record Information

Version

2.0

Created at

2021-06-21 00:16:28 UTC

Updated at

2021-06-30 00:17:53 UTC

NP-MRD ID

NP0042667

Secondary Accession Numbers

None

Natural Product Identification

Common Name

saccharonol A

Provided By

JEOL Database JEOL Logo

Description

saccharonol A is found in Conoideocrella tenuis, Saccharomonospora azurea and Streptomyces eurocidicus. saccharonol A was first documented in 2013 (Singh, B., et al.). Based on a literature review very few articles have been published on 6,8-dihydroxy-3-methyl-1H-isochromen-1-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102163D          

 22 23  0  0  0  0            999 V2000
   -0.4631   -1.2950   -3.5568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1720   -0.2470   -2.5312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6315    1.0080   -2.5973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2816    1.9427   -1.5382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7428    3.2638   -1.5718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3988    4.1454   -0.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8736    5.4210   -0.6299 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4002    3.7358    0.5108 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8603    2.4210    0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6425    2.0864    1.6203 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.5195   -0.4753 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0101    0.1234   -0.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7173   -0.2587    0.4885 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6423   -0.6970   -1.4672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9804   -2.1419   -3.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4692   -1.6589   -4.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0951   -0.9135   -4.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2562    1.3470   -3.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3696    3.6181   -2.3866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5583    5.9215    0.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6736    4.4157    1.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053    1.1417    1.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  8  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  4  3  1  0  0  0  0
 11 12  1  0  0  0  0
 12 14  1  0  0  0  0
 14  2  1  0  0  0  0
  2  3  2  0  0  0  0
  4 11  1  0  0  0  0
 12 13  2  0  0  0  0
  2  1  1  0  0  0  0
  8  9  1  0  0  0  0
  6  7  1  0  0  0  0
  9 11  2  0  0  0  0
  9 10  1  0  0  0  0
  8 21  1  0  0  0  0
  5 19  1  0  0  0  0
  3 18  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
  7 20  1  0  0  0  0
 10 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042667

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H8O4/c1-5-2-6-3-7(11)4-8(12)9(6)10(13)14-5/h2-4,11-12H,1H3

> <INCHI_KEY>
OHHKDUWFPNAEHQ-UHFFFAOYSA-N

> <FORMULA>
C10H8O4

> <MOLECULAR_WEIGHT>
192.17

> <EXACT_MASS>
192.042258738

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
18.460656856544155

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,8-dihydroxy-3-methyl-1H-isochromen-1-one

> <ALOGPS_LOGP>
1.68

> <JCHEM_LOGP>
2.2983323979999994

> <ALOGPS_LOGS>
-1.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.271087452429507

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.4299716055136

> <JCHEM_PKA_STRONGEST_BASIC>
-4.021447429392688

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
51.26690000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.68e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4-dehydro-6-hydroxymellein

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.463  -1.295  -3.557  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.172  -0.247  -2.531  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.632   1.008  -2.597  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.282   1.943  -1.538  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.743   3.264  -1.572  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.399   4.145  -0.550  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.874   5.421  -0.630  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.400   3.736   0.511  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.860   2.421   0.546  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.643   2.086   1.620  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.523   1.520  -0.475  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.010   0.123  -0.440  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.717  -0.259   0.489  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.642  -0.697  -1.467  0.00  0.00           O+0
HETATM   15  H   UNK     0      -0.980  -2.142  -3.095  0.00  0.00           H+0
HETATM   16  H   UNK     0       0.469  -1.659  -4.000  0.00  0.00           H+0
HETATM   17  H   UNK     0      -1.095  -0.914  -4.365  0.00  0.00           H+0
HETATM   18  H   UNK     0      -1.256   1.347  -3.417  0.00  0.00           H+0
HETATM   19  H   UNK     0      -1.370   3.618  -2.387  0.00  0.00           H+0
HETATM   20  H   UNK     0      -0.558   5.922   0.142  0.00  0.00           H+0
HETATM   21  H   UNK     0       0.674   4.416   1.312  0.00  0.00           H+0
HETATM   22  H   UNK     0       1.905   1.142   1.537  0.00  0.00           H+0
CONECT    1    2   15   16   17                                             
CONECT    2   14    3    1                                                  
CONECT    3    4    2   18                                                  
CONECT    4    5    3   11                                                  
CONECT    5    4    6   19                                                  
CONECT    6    8    5    7                                                  
CONECT    7    6   20                                                       
CONECT    8    6    9   21                                                  
CONECT    9    8   11   10                                                  
CONECT   10    9   22                                                       
CONECT   11   12    4    9                                                  
CONECT   12   11   14   13                                                  
CONECT   13   12                                                            
CONECT   14   12    2                                                       
CONECT   15    1                                                            
CONECT   16    1                                                            
CONECT   17    1                                                            
CONECT   18    3                                                            
CONECT   19    5                                                            
CONECT   20    7                                                            
CONECT   21    8                                                            
CONECT   22   10                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₈O₄

Average Mass

192.1700 Da

Monoisotopic Mass

192.04226 Da

IUPAC Name

6,8-dihydroxy-3-methyl-1H-isochromen-1-one

Traditional Name

3,4-dehydro-6-hydroxymellein

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C10H8O4/c1-5-2-6-3-7(11)4-8(12)9(6)10(13)14-5/h2-4,11-12H,1H3

InChI Key

OHHKDUWFPNAEHQ-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, 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
Conoideocrella tenuis	LOTUS Database	35616633
Saccharomonospora azurea	JEOL database	Singh, B., et al, Tetrahedron Lett. 54, 6695 (2013)
Streptomyces eurocidicus	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Ceratocystis minor	KNApSAcK Database	22123792
Colletotrichum lagenarium	KNApSAcK Database	22123792
Torrubiella tenuis BCC12732	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as isocoumarins and derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isocoumarins and derivatives

Sub Class

Not Available

Direct Parent

Isocoumarins and derivatives

Alternative Parents

Substituents

Isocoumarin
Benzopyran
2-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Lactone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isocoumarins (CHEBI:1369 )

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	1.68	ALOGPS
logP	2.3	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	8.43	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	51.27 m³·mol⁻¹	ChemAxon
Polarizability	18.46 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00000551

Chemspider ID

4444232

KEGG Compound ID

C03830

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

Singh, B., et al. (2013). Singh, B., et al, Tetrahedron Lett. 54, 6695 (2013). Tetrahedron Lett.

Showing NP-Card for saccharonol A (NP0042667)

MOL for NP0042667 (saccharonol A)

3D MOL for NP0042667 (saccharonol A)

3D SDF for NP0042667 (saccharonol A)

3D-SDF for NP0042667 (saccharonol A)

PDB for NP0042667 (saccharonol A)

3D PDB for NP0042667 (saccharonol A)

SMILES for NP0042667 (saccharonol A)

INCHI for NP0042667 (saccharonol A)

Structure for NP0042667 (saccharonol A)

3D Structure for NP0042667 (saccharonol A)