NP-MRD: Showing NP-Card for Puberulic acid (NP0006400)

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Record Information

Version

2.0

Created at

2020-12-09 03:25:35 UTC

Updated at

2021-07-15 16:54:41 UTC

NP-MRD ID

NP0006400

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Puberulic acid

Provided By

NPAtlas

Description

Puberulic acid is found in Penicillium aurantiogriseum and Penicillium puberulum. Puberulic acid was first documented in 1932 (PMID: 16744843). Based on a literature review very few articles have been published on 4,6,7-trihydroxy-1H,3H,5H-cyclohepta[c]furan-1,3,5-trione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118273D          

 20 21  0  0  0  0            999 V2000
    2.6626   -2.9228   -0.0648 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3569   -1.7045   -0.1070 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3217   -0.6916   -0.1928 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6392    0.5183   -0.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1772    1.6650   -0.2930 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2103    0.2290   -0.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0286   -1.1498   -0.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1531   -1.8587    0.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4636   -1.3711    0.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4014   -2.2080    0.0493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9228   -0.0578    0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2942    0.1603    0.1344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1210    1.0567    0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7038    2.1466    0.8333 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2123    1.1851   -0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6020    2.4128   -0.6180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473   -2.9350    0.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8808   -0.6522    0.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1798    2.9953    0.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0429    3.1823   -0.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
  7  2  1  0  0  0  0
 15  6  2  0  0  0  0
  8 17  1  0  0  0  0
 12 18  1  0  0  0  0
 14 19  1  0  0  0  0
 16 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006400

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=O)OC(=O)C2=C([H])C(=O)C(O[H])=C1O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C9H4O7/c10-3-1-2-4(9(15)16-8(2)14)6(12)7(13)5(3)11/h1H,(H3,10,11,12,13)

> <INCHI_KEY>
JAJRKOVXTSKCLS-UHFFFAOYSA-N

> <FORMULA>
C9H4O7

> <MOLECULAR_WEIGHT>
224.124

> <EXACT_MASS>
223.995702469

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
18.058363889836908

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,7,8-trihydroxy-1H,3H,5H-cyclohepta[c]furan-1,3,5-trione

> <ALOGPS_LOGP>
-0.75

> <JCHEM_LOGP>
-0.2395834753333333

> <ALOGPS_LOGS>
-2.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.81829323327968

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.360848932863144

> <JCHEM_PKA_STRONGEST_BASIC>
2.0335005387126266

> <JCHEM_POLAR_SURFACE_AREA>
121.13000000000001

> <JCHEM_REFRACTIVITY>
50.6966

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,7,8-trihydroxycyclohepta[c]furan-1,3,5-trione

> <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  O   UNK     0       2.663  -2.923  -0.065  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.357  -1.704  -0.107  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.322  -0.692  -0.193  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.639   0.518  -0.219  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.177   1.665  -0.293  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.210   0.229  -0.146  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.029  -1.150  -0.077  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.153  -1.859   0.004  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.464  -1.371   0.069  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.401  -2.208   0.049  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.923  -0.058   0.156  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.294   0.160   0.134  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.121   1.057   0.263  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.704   2.147   0.833  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.212   1.185  -0.148  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.602   2.413  -0.618  0.00  0.00           O+0
HETATM   17  H   UNK     0      -0.047  -2.935   0.019  0.00  0.00           H+0
HETATM   18  H   UNK     0      -3.881  -0.652   0.057  0.00  0.00           H+0
HETATM   19  H   UNK     0      -1.180   2.995   0.955  0.00  0.00           H+0
HETATM   20  H   UNK     0      -0.043   3.182  -0.674  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   15                                                  
CONECT    7    6    8    2                                                  
CONECT    8    7    9   17                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11   18                                                       
CONECT   13   11   14   15                                                  
CONECT   14   13   19                                                       
CONECT   15   13   16    6                                                  
CONECT   16   15   20                                                       
CONECT   17    8                                                            
CONECT   18   12                                                            
CONECT   19   14                                                            
CONECT   20   16                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Puberulonate	Generator

Chemical Formula

C₉H₄O₇

Average Mass

224.1240 Da

Monoisotopic Mass

223.99570 Da

IUPAC Name

6,7,8-trihydroxy-1H,3H,5H-cyclohepta[c]furan-1,3,5-trione

Traditional Name

6,7,8-trihydroxycyclohepta[c]furan-1,3,5-trione

CAS Registry Number

Not Available

SMILES

OC1=C2C(=O)OC(=O)C2=CC(=O)C(O)=C1O

InChI Identifier

InChI=1S/C9H4O7/c10-3-1-2-4(9(15)16-8(2)14)6(12)7(13)5(3)11/h1H,(H3,10,11,12,13)

InChI Key

JAJRKOVXTSKCLS-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 aurantiogriseum	LOTUS Database	35616633
Penicillium puberulum	NPAtlas	16744843

Chemical Taxonomy

Classification

Not classified

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	-0.75	ALOGPS
logP	-0.24	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	5.36	ChemAxon
pKa (Strongest Basic)	2.03	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.13 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	50.7 m³·mol⁻¹	ChemAxon
Polarizability	18.06 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

NPA017682

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

16735989

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54684723

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Birkinshaw JH, Raistrick H: Studies in the biochemistry of micro-organisms: Puberulic acid C(8)H(6)O(6) and an acid C(8)H(4)O(6), new products of the metabolism of glucose by Penicillium puberulum Bainier and Penicillium aurantio-virens Biourge. With an appendix on certain dihydroxybenzenedicarboxylic acids. Biochem J. 1932;26(2):441-53. doi: 10.1042/bj0260441. [PubMed:16744843 ]

Showing NP-Card for Puberulic acid (NP0006400)

MOL for NP0006400 (Puberulic acid)

3D MOL for NP0006400 (Puberulic acid)

3D SDF for NP0006400 (Puberulic acid)

3D-SDF for NP0006400 (Puberulic acid)

PDB for NP0006400 (Puberulic acid)

3D PDB for NP0006400 (Puberulic acid)

SMILES for NP0006400 (Puberulic acid)

INCHI for NP0006400 (Puberulic acid)

Structure for NP0006400 (Puberulic acid)

3D Structure for NP0006400 (Puberulic acid)