NP-MRD: Showing NP-Card for Viticolin B (NP0001558)

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Record Information

Version

2.0

Created at

2020-09-21 21:11:20 UTC

Updated at

2021-08-10 02:55:13 UTC

NP-MRD ID

NP0001558

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Viticolin B

Provided By

NPAtlas

Description

5-Hydroxy-4,6-dimethoxy-3-oxocyclohepta-1,4,6-triene-1-carboxylic acid belongs to the class of organic compounds known as tropones. Tropones are compounds containing a tropone ring, which is a cycloheptatrienone ring bearing a ketone group. Viticolin B is found in Penicillium. Based on a literature review very few articles have been published on 5-hydroxy-4,6-dimethoxy-3-oxocyclohepta-1,4,6-triene-1-carboxylic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117433D          

 26 26  0  0  0  0            999 V2000
    3.4759   -0.7960    0.5975 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6068    0.2680    0.2568 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2590    0.0915    0.0207 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7952   -1.1908    0.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4928   -1.6876   -0.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6603   -3.1124    0.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3284   -3.8011    0.4709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8873   -3.7204   -0.0315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6509   -1.0299   -0.4321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7938    0.3249   -0.6354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9734    0.6734   -0.8918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8192    1.3322   -0.5934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2818    2.6095   -0.8846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7714    3.4999    0.0913 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5184    1.1970   -0.3014 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2373    2.3728   -0.3388 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5172   -0.4655    0.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1374   -1.2410    1.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4795   -1.6072   -0.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5482   -1.9079    0.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1233   -4.6002    0.4199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5362   -1.6659   -0.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4966    3.1562    1.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3629    4.5187   -0.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8928    3.5040   -0.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8396    3.2780   -0.5602 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  5  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15  3  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  4 20  1  0  0  0  0
  8 21  1  0  0  0  0
  9 22  1  0  0  0  0
 14 23  1  0  0  0  0
 14 24  1  0  0  0  0
 14 25  1  0  0  0  0
 16 26  1  0  0  0  0
M  END


  Mrv1652306242117433D          

 26 26  0  0  0  0            999 V2000
    3.4759   -0.7960    0.5975 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6068    0.2680    0.2568 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2590    0.0915    0.0207 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7952   -1.1908    0.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4928   -1.6876   -0.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6603   -3.1124    0.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3284   -3.8011    0.4709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8873   -3.7204   -0.0315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6509   -1.0299   -0.4321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7938    0.3249   -0.6354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9734    0.6734   -0.8918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8192    1.3322   -0.5934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2818    2.6095   -0.8846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7714    3.4999    0.0913 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5184    1.1970   -0.3014 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2373    2.3728   -0.3388 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5172   -0.4655    0.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1374   -1.2410    1.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4795   -1.6072   -0.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5482   -1.9079    0.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1233   -4.6002    0.4199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5362   -1.6659   -0.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4966    3.1562    1.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3629    4.5187   -0.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8928    3.5040   -0.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8396    3.2780   -0.5602 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  5  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15  3  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  4 20  1  0  0  0  0
  8 21  1  0  0  0  0
  9 22  1  0  0  0  0
 14 23  1  0  0  0  0
 14 24  1  0  0  0  0
 14 25  1  0  0  0  0
 16 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001558

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O6/c1-15-7-4-5(10(13)14)3-6(11)9(16-2)8(7)12/h3-4,12H,1-2H3,(H,13,14)

> <INCHI_KEY>
WVBPTDMOPNMMDP-UHFFFAOYSA-N

> <FORMULA>
C10H10O6

> <MOLECULAR_WEIGHT>
226.184

> <EXACT_MASS>
226.047738042

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
21.138505752784805

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-4,6-dimethoxy-3-oxocyclohepta-1,4,6-triene-1-carboxylic acid

> <ALOGPS_LOGP>
0.30

> <JCHEM_LOGP>
-0.5460456630372594

> <ALOGPS_LOGS>
-2.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.95390123151586

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5111460674057757

> <JCHEM_PKA_STRONGEST_BASIC>
2.5181424319465613

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
57.40520000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.57e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-4,6-dimethoxy-3-oxocyclohepta-1,4,6-triene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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  C   UNK     0       3.476  -0.796   0.598  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.607   0.268   0.257  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.259   0.092   0.021  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.795  -1.191   0.135  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.493  -1.688  -0.066  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.660  -3.112   0.137  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.328  -3.801   0.471  0.00  0.00           O+0
HETATM    8  O   UNK     0      -1.887  -3.720  -0.032  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.651  -1.030  -0.432  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.794   0.325  -0.635  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.973   0.673  -0.892  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.819   1.332  -0.593  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.282   2.610  -0.885  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.771   3.500   0.091  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.518   1.197  -0.301  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.237   2.373  -0.339  0.00  0.00           O+0
HETATM   17  H   UNK     0       4.517  -0.466   0.717  0.00  0.00           H+0
HETATM   18  H   UNK     0       3.137  -1.241   1.556  0.00  0.00           H+0
HETATM   19  H   UNK     0       3.479  -1.607  -0.160  0.00  0.00           H+0
HETATM   20  H   UNK     0       1.548  -1.908   0.423  0.00  0.00           H+0
HETATM   21  H   UNK     0      -2.123  -4.600   0.420  0.00  0.00           H+0
HETATM   22  H   UNK     0      -2.536  -1.666  -0.571  0.00  0.00           H+0
HETATM   23  H   UNK     0      -1.497   3.156   1.117  0.00  0.00           H+0
HETATM   24  H   UNK     0      -1.363   4.519  -0.052  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.893   3.504  -0.018  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.840   3.278  -0.560  0.00  0.00           H+0
CONECT    1    2   17   18   19                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5   20                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6   21                                                       
CONECT    9    5   10   22                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13   23   24   25                                             
CONECT   15   12   16    3                                                  
CONECT   16   15   26                                                       
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    4                                                            
CONECT   21    8                                                            
CONECT   22    9                                                            
CONECT   23   14                                                            
CONECT   24   14                                                            
CONECT   25   14                                                            
CONECT   26   16                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   52    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
5-Hydroxy-4,6-dimethoxy-3-oxocyclohepta-1,4,6-triene-1-carboxylate	Generator

Chemical Formula

C₁₀H₁₀O₆

Average Mass

226.1840 Da

Monoisotopic Mass

226.04774 Da

IUPAC Name

5-hydroxy-4,6-dimethoxy-3-oxocyclohepta-1,4,6-triene-1-carboxylic acid

Traditional Name

5-hydroxy-4,6-dimethoxy-3-oxocyclohepta-1,4,6-triene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C1=C([H])C(=O)C(OC([H])([H])[H])=C(O[H])C(OC([H])([H])[H])=C1[H]

InChI Identifier

InChI=1S/C10H10O6/c1-15-7-4-5(10(13)14)3-6(11)9(16-2)8(7)12/h3-4,12H,1-2H3,(H,13,14)

InChI Key

WVBPTDMOPNMMDP-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600Mz MHz, Methanol, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600Mz, Methanol, simulated)	jeffreyavansanten@gmail.com	Not Available	Not Available	2020-09-21	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Penicillium	NPAtlas	21063422

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tropones. Tropones are compounds containing a tropone ring, which is a cycloheptatrienone ring bearing a ketone group.

Kingdom

Organic compounds

Super Class

Hydrocarbon derivatives

Class

Tropones

Sub Class

Not Available

Direct Parent

Tropones

Alternative Parents

Substituents

Tropone
Alkyl aryl ether
Vinylogous acid
Cyclic ketone
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
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	0.3	ALOGPS
logP	-0.55	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	3.51	ChemAxon
pKa (Strongest Basic)	2.52	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	57.41 m³·mol⁻¹	ChemAxon
Polarizability	21.14 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA000009

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78434593

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

51350070

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Viticolin B (NP0001558)

MOL for NP0001558 (Viticolin B)

3D MOL for NP0001558 (Viticolin B)

3D SDF for NP0001558 (Viticolin B)

3D-SDF for NP0001558 (Viticolin B)

PDB for NP0001558 (Viticolin B)

3D PDB for NP0001558 (Viticolin B)

SMILES for NP0001558 (Viticolin B)

INCHI for NP0001558 (Viticolin B)

Structure for NP0001558 (Viticolin B)

3D Structure for NP0001558 (Viticolin B)