NP-MRD: Showing NP-Card for Terrestrol F (NP0007478)

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Record Information

Version

2.0

Created at

2020-12-09 04:21:02 UTC

Updated at

2021-07-15 16:57:42 UTC

NP-MRD ID

NP0007478

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Terrestrol F

Provided By

NPAtlas

Description

Terrestrol F is found in Penicillium solitum and Penicillium terrestre. Based on a literature review very few articles have been published on Terrestrol F.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118403D          

 33 34  0  0  0  0            999 V2000
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   -2.4916    2.0933   -0.2288 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -3.3327   -0.1716    0.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6267    0.3383   -0.0789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2081   -1.5080    0.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6291   -2.5407    0.2753 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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    1.5000   -0.6337   -3.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306242118403D          

 33 34  0  0  0  0            999 V2000
   -1.4343    2.9507   -0.2891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4916    2.0933   -0.2288 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2028    0.6705   -0.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3327   -0.1716    0.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2081   -1.5080    0.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0007478

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(O[H])C(=C1[H])C([H])([H])C1=C(O[H])C([H])=C(Cl)C(O[H])=C1C([H])([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C14H13ClO5/c15-11-5-13(19)9(10(6-16)14(11)20)4-7-3-8(17)1-2-12(7)18/h1-3,5,16-20H,4,6H2

> <INCHI_KEY>
MOJQIPGXOWLFII-UHFFFAOYSA-N

> <FORMULA>
C14H13ClO5

> <MOLECULAR_WEIGHT>
296.7

> <EXACT_MASS>
296.0451512

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
28.828896428573195

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-chloro-2-[(2,5-dihydroxyphenyl)methyl]-3-(hydroxymethyl)benzene-1,4-diol

> <ALOGPS_LOGP>
1.58

> <JCHEM_LOGP>
2.6874734653333325

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.7528610920698

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.420871855316569

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0087473411858383

> <JCHEM_POLAR_SURFACE_AREA>
101.15

> <JCHEM_REFRACTIVITY>
75.3395

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.46e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
terrestrol F

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
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  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 11  3  1  0
 19 13  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  5 24  1  0
  8 25  1  0
 10 26  1  0
 12 27  1  0
 12 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 20 33  1  0
M  END

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  O   UNK     0      -1.434   2.951  -0.289  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.492   2.093  -0.229  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.203   0.671  -0.054  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.333  -0.172   0.019  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.627   0.338  -0.079  0.00  0.00           O+0
HETATM    6  C   UNK     0      -3.208  -1.508   0.188  0.00  0.00           C+0
HETATM    7 Cl   UNK     0      -4.629  -2.541   0.275  0.00  0.00          Cl+0
HETATM    8  C   UNK     0      -1.959  -2.061   0.291  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.855  -1.226   0.218  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.378  -1.805   0.326  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.946   0.150   0.044  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.238   1.021  -0.039  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.532   0.316  -0.028  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.257   0.275   1.138  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.461  -0.384   1.135  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.194  -0.417   2.340  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.940  -0.992  -0.004  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.205  -0.954  -1.194  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.997  -0.288  -1.175  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.254  -0.239  -2.344  0.00  0.00           O+0
HETATM   21  H   UNK     0      -1.544   3.773   0.261  0.00  0.00           H+0
HETATM   22  H   UNK     0      -3.129   2.441   0.640  0.00  0.00           H+0
HETATM   23  H   UNK     0      -3.191   2.211  -1.110  0.00  0.00           H+0
HETATM   24  H   UNK     0      -4.772   1.324  -0.203  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.884  -3.130   0.428  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.534  -2.795   0.452  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.186   1.607  -1.021  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.274   1.793   0.746  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.904   0.745   2.056  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.846   0.376   2.441  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.896  -1.495   0.058  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.609  -1.443  -2.070  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.500  -0.634  -3.218  0.00  0.00           H+0
CONECT    1    2   21                                                       
CONECT    2    1    3   22   23                                             
CONECT    3    2    4   11                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4   24                                                       
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   25                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9   26                                                       
CONECT   11    9   12    3                                                  
CONECT   12   11   13   27   28                                             
CONECT   13   12   14   19                                                  
CONECT   14   13   15   29                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   30                                                       
CONECT   17   15   18   31                                                  
CONECT   18   17   19   32                                                  
CONECT   19   18   20   13                                                  
CONECT   20   19   33                                                       
CONECT   21    1                                                            
CONECT   22    2                                                            
CONECT   23    2                                                            
CONECT   24    5                                                            
CONECT   25    8                                                            
CONECT   26   10                                                            
CONECT   27   12                                                            
CONECT   28   12                                                            
CONECT   29   14                                                            
CONECT   30   16                                                            
CONECT   31   17                                                            
CONECT   32   18                                                            
CONECT   33   20                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

RDKit          3D

33 34  0  0  0  0  0  0  0  0999 V2000
   -1.4343    2.9507   -0.2891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4916    2.0933   -0.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2028    0.6705   -0.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3327   -0.1716    0.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6267    0.3383   -0.0789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2081   -1.5080    0.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6291   -2.5407    0.2753 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.9588   -2.0607    0.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8546   -1.2264    0.2177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3779   -1.8052    0.3255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9459    0.1500    0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2381    1.0212   -0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5318    0.3162   -0.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2570    0.2750    1.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4611   -0.3838    1.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1940   -0.4172    2.3396 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9398   -0.9924   -0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2047   -0.9537   -1.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9974   -0.2883   -1.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2541   -0.2393   -2.3440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5436    3.7730    0.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1287    2.4406    0.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1912    2.2106   -1.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7722    1.3241   -0.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8835   -3.1295    0.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5336   -2.7953    0.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1858    1.6065   -1.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2737    1.7932    0.7461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9039    0.7452    2.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8459    0.3759    2.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8960   -1.4954    0.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6089   -1.4432   -2.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000   -0.6337   -3.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 11  3  1  0
 19 13  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  5 24  1  0
  8 25  1  0
 10 26  1  0
 12 27  1  0
 12 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 20 33  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₄H₁₃ClO₅

Average Mass

296.7000 Da

Monoisotopic Mass

296.04515 Da

IUPAC Name

5-chloro-2-[(2,5-dihydroxyphenyl)methyl]-3-(hydroxymethyl)benzene-1,4-diol

Traditional Name

terrestrol F

CAS Registry Number

Not Available

SMILES

OCC1=C(CC2=C(O)C=CC(O)=C2)C(O)=CC(Cl)=C1O

InChI Identifier

InChI=1S/C14H13ClO5/c15-11-5-13(19)9(10(6-16)14(11)20)4-7-3-8(17)1-2-12(7)18/h1-3,5,16-20H,4,6H2

InChI Key

MOJQIPGXOWLFII-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
Penicillium solitum	LOTUS Database	35616633
Penicillium terrestre	NPAtlas	18163588

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
1,4-dihydroxy-2-halobenzenoid
Chlorohydroquinone
Benzyl alcohol
3-halophenol
2-halophenol
Hydroquinone
3-chlorophenol
2-chlorophenol
Chlorobenzene
Halobenzene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aryl halide
Aryl chloride
Organochloride
Organohalogen compound
Alcohol
Organooxygen compound
Primary alcohol
Aromatic alcohol
Organic oxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	1.58	ALOGPS
logP	2.69	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.42	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	101.15 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	75.34 m³·mol⁻¹	ChemAxon
Polarizability	28.83 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

NPA009478

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00040469

Chemspider ID

23314347

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24770506

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Terrestrol F (NP0007478)

MOL for NP0007478 (Terrestrol F)

3D MOL for NP0007478 (Terrestrol F)

3D SDF for NP0007478 (Terrestrol F)

3D-SDF for NP0007478 (Terrestrol F)

PDB for NP0007478 (Terrestrol F)

3D PDB for NP0007478 (Terrestrol F)

SMILES for NP0007478 (Terrestrol F)

INCHI for NP0007478 (Terrestrol F)

Structure for NP0007478 (Terrestrol F)

3D Structure for NP0007478 (Terrestrol F)