NP-MRD: Showing NP-Card for Variolaric acid (NP0077347)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 22:30:36 UTC

Updated at

2022-04-28 22:30:37 UTC

NP-MRD ID

NP0077347

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Variolaric acid

Description

Variolaric acid, also known as variolarate, belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups. Variolaric acid is found in Ochrolechia parella and Ramalina hierrensis. Variolaric acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 36  0  0  0  0  0  0  0  0999 V2000
    3.7628    2.1713    0.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475    0.8153   -0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0943   -0.3042   -0.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6352   -1.5856   -0.3987 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5827   -2.6226   -0.4182 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2980   -1.8265   -0.5717 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4285   -0.7688   -0.5416 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9050    0.5128   -0.3395 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1233    1.7432   -0.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7730    2.7546   -0.6301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2217    1.9075    0.0980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1947    0.8942    0.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4186    1.4098    0.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5556    0.6061    0.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4119   -0.7182    0.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1873   -1.2171   -0.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0286   -2.5398   -0.6562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0426   -0.4241   -0.3226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0907   -1.1459   -0.7301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7136   -1.3268    0.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9897   -2.5355   -0.0635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5957   -0.3490    0.6058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9692    0.8815    0.7892 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0251    2.7649   -0.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8222    1.9849    0.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3746    2.7098    0.9491 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1444   -0.1229   -0.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8515   -3.1159    0.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9407   -2.8229   -0.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5165    2.4550    0.6937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8223   -3.1424   -0.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3539    1.6822    0.1232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0778    1.2747    1.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
  8  2  1  0
 18 12  1  0
 19  7  1  0
 23 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  5 28  1  0
  6 29  1  0
 13 30  1  0
 23 32  1  0
 23 33  1  0
 17 31  1  0
M  END


  Mrv1533004251509362D          

 23 26  0  0  0  0            999 V2000
    0.7336   -2.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9699   -1.9096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4035   -1.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6397   -0.5193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0733    0.0805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4424   -0.3287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0088   -0.9285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7741   -0.6204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4922   -1.0267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1327   -0.5067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0026    0.3080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9033   -0.8013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6379   -0.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7659    0.3891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2220   -1.0085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8484   -1.7440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0333   -1.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3929   -2.1360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6223   -1.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0664   -2.4510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2432   -2.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8370   -3.1146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7726   -1.7190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  2 23  1  0  0  0  0
  7 23  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0077347

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(O)=CC2=C1C(=O)OC1=CC3=C(C(=O)OC3)C(O)=C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C16H10O7/c1-6-2-8(17)4-9-11(6)16(20)23-10-3-7-5-21-15(19)12(7)13(18)14(10)22-9/h2-4,17-18H,5H2,1H3

> <INCHI_KEY>
LPUOVEFMUOQBFV-UHFFFAOYSA-N

> <FORMULA>
C16H10O7

> <MOLECULAR_WEIGHT>
314.249

> <EXACT_MASS>
314.042652662

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
29.392750027217346

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,18-dihydroxy-7-methyl-2,10,15-trioxatetracyclo[9.7.0.0³,⁸.0¹³,¹⁷]octadeca-1(18),3(8),4,6,11,13(17)-hexaene-9,16-dione

> <ALOGPS_LOGP>
2.29

> <JCHEM_LOGP>
3.0727176069999995

> <ALOGPS_LOGS>
-3.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.500447234436749

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.888670463602342

> <JCHEM_PKA_STRONGEST_BASIC>
-3.833703860403333

> <JCHEM_POLAR_SURFACE_AREA>
102.28999999999999

> <JCHEM_REFRACTIVITY>
77.6266

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.26e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,18-dihydroxy-7-methyl-2,10,15-trioxatetracyclo[9.7.0.0³,⁸.0¹³,¹⁷]octadeca-1(18),3(8),4,6,11,13(17)-hexaene-9,16-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       1.369  -5.040   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.810  -3.565   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.753  -2.445   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.194  -0.969   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.137   0.150   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.693  -0.614   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.750  -1.733   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.178  -1.158   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.519  -1.916   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.714  -0.946   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.471   0.575   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.153  -1.496   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.524  -0.795   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.763   0.726   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      11.614  -1.883   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.917  -3.256   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.396  -3.017   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.200  -3.987   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.762  -3.437   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.724  -4.575   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.187  -4.474   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.429  -5.814   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.309  -3.209   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   23                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   19                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   17                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18    9   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    2    7                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Value	Source
Variolarate	Generator

Chemical Formula

C₁₆H₁₀O₇

Average Mass

314.2490 Da

Monoisotopic Mass

314.04265 Da

IUPAC Name

5,18-dihydroxy-7-methyl-2,10,15-trioxatetracyclo[9.7.0.0³,⁸.0¹³,¹⁷]octadeca-1(18),3(8),4,6,11,13(17)-hexaene-9,16-dione

Traditional Name

5,18-dihydroxy-7-methyl-2,10,15-trioxatetracyclo[9.7.0.0³,⁸.0¹³,¹⁷]octadeca-1(18),3(8),4,6,11,13(17)-hexaene-9,16-dione

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=CC2=C1C(=O)OC1=CC3=C(C(=O)OC3)C(O)=C1O2

InChI Identifier

InChI=1S/C16H10O7/c1-6-2-8(17)4-9-11(6)16(20)23-10-3-7-5-21-15(19)12(7)13(18)14(10)22-9/h2-4,17-18H,5H2,1H3

InChI Key

LPUOVEFMUOQBFV-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
Ochrolechia parella	-	KNApSAcK
Ramalina hierrensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Diarylethers

Alternative Parents

Substituents

Diaryl ether
Isobenzofuranone
Phthalide
Isocoumaran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
1,4-dioxepine
Dioxepine
Dicarboxylic acid or derivatives
Benzenoid
Vinylogous acid
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
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	2.29	ALOGPS
logP	3.07	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	7.89	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.29 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	77.63 m³·mol⁻¹	ChemAxon
Polarizability	29.39 Å³	ChemAxon
Number of Rings	4	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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12444681

PDB ID

Not Available

ChEBI ID

144244

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Variolaric acid (NP0077347)

MOL for NP0077347 (Variolaric acid)

3D MOL for NP0077347 (Variolaric acid)

3D SDF for NP0077347 (Variolaric acid)

3D-SDF for NP0077347 (Variolaric acid)

PDB for NP0077347 (Variolaric acid)

3D PDB for NP0077347 (Variolaric acid)

SMILES for NP0077347 (Variolaric acid)

INCHI for NP0077347 (Variolaric acid)

Structure for NP0077347 (Variolaric acid)

3D Structure for NP0077347 (Variolaric acid)