NP-MRD: Showing NP-Card for scytalone (NP0176127)

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Record Information

Version

2.0

Created at

2022-09-03 13:44:30 UTC

Updated at

2022-09-03 13:44:31 UTC

NP-MRD ID

NP0176127

Secondary Accession Numbers

None

Natural Product Identification

Common Name

scytalone

Description

scytalone is found in Cytospora populina, Phialocephala lagerbergii, Valsa ambiens and Verticillium dahliae.

Structure

MOL 3D MOL SDF PDB SMILES InChI

 
  Mrv1533006081517182D          
 
 14 15  0  0  1  0            999 V2000
   12.9563  -10.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9563   -9.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2429  -10.7021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6732  -10.7021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2429   -9.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6695   -9.0514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5409  -10.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3903  -10.2913    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.5409   -9.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2429   -8.2484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3865   -9.4622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6658   -8.2373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8760  -10.6498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1371  -10.7394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  2  0  0  0  0
  4  8  1  0  0  0  0
  5  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  2  0  0  0  0
  7 13  1  0  0  0  0
  8 14  1  1  0  0  0
  7  9  1  0  0  0  0
  8 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0176127

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1CC(=O)C2=C(C1)C=C(O)C=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O4/c11-6-1-5-2-7(12)4-9(14)10(5)8(13)3-6/h1,3,7,11-13H,2,4H2/t7-/m0/s1

> <INCHI_KEY>
RTWVXIIKUFSDJB-ZETCQYMHSA-N

> <FORMULA>
C10H10O4

> <MOLECULAR_WEIGHT>
194.186

> <EXACT_MASS>
194.057908802

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
18.806526377543243

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-3,6,8-trihydroxy-1,2,3,4-tetrahydronaphthalen-1-one

> <ALOGPS_LOGP>
0.25

> <JCHEM_LOGP>
1.0931829579999999

> <ALOGPS_LOGS>
-1.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.403367932288488

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.760432657761878

> <JCHEM_PKA_STRONGEST_BASIC>
-2.847285041463751

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
49.803999999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.43e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
scytalone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-JUN-15         0                                  
HETATM    1  C   UNK     0      24.185 -19.203   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.185 -17.670   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.853 -19.977   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.523 -19.977   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.853 -16.917   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.516 -16.896   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.543 -19.203   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.862 -19.211   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.543 -17.670   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      22.853 -15.397   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      26.855 -17.663   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      25.509 -15.376   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      20.302 -19.880   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      28.256 -20.047   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9   10                                                  
CONECT    6    2   11   12                                                  
CONECT    7    3   13    9                                                  
CONECT    8    4   14   11                                                  
CONECT    9    5    7                                                       
CONECT   10    5                                                            
CONECT   11    6    8                                                       
CONECT   12    6                                                            
CONECT   13    7                                                            
CONECT   14    8                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Value	Source
3,4-Dihydro-3,6,8-trihydoroxy-1(2H)-napthalenone	Kegg
3,4-dihydro-3,6,8-Trihydroxy-1(2H)naphthalenone	MeSH
3,4-dihydro-3,6,8-Trihydroxy-1-(2H)-naphthalenone	MeSH
Scytolone	MeSH

Chemical Formula

C₁₀H₁₀O₄

Average Mass

194.1860 Da

Monoisotopic Mass

194.05791 Da

IUPAC Name

(3S)-3,6,8-trihydroxy-1,2,3,4-tetrahydronaphthalen-1-one

Traditional Name

scytalone

CAS Registry Number

Not Available

SMILES

O[C@@H]1CC(=O)C2=C(C1)C=C(O)C=C2O

InChI Identifier

InChI=1S/C10H10O4/c11-6-1-5-2-7(12)4-9(14)10(5)8(13)3-6/h1,3,7,11-13H,2,4H2/t7-/m0/s1

InChI Key

RTWVXIIKUFSDJB-ZETCQYMHSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Cytospora populina	LOTUS Database	35616633
Phialocephala lagerbergii	LOTUS Database	35616633
Valsa ambiens	LOTUS Database	35616633
Verticillium dahliae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Tetralins

Sub Class

Not Available

Direct Parent

Tetralins

Alternative Parents

Substituents

Tetralin
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Secondary alcohol
Ketone
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	0.25	ALOGPS
logP	1.09	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	7.76	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	49.8 m³·mol⁻¹	ChemAxon
Polarizability	18.81 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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C00779

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439309

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for scytalone (NP0176127)

MOL for NP0176127 (scytalone)

3D MOL for NP0176127 (scytalone)

3D SDF for NP0176127 (scytalone)

3D-SDF for NP0176127 (scytalone)

PDB for NP0176127 (scytalone)

3D PDB for NP0176127 (scytalone)

SMILES for NP0176127 (scytalone)

INCHI for NP0176127 (scytalone)

Structure for NP0176127 (scytalone)

3D Structure for NP0176127 (scytalone)