NP-MRD: Showing NP-Card for stipitatonic acid (NP0170855)

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Record Information

Version

2.0

Created at

2022-09-03 07:08:13 UTC

Updated at

2022-09-03 07:08:14 UTC

NP-MRD ID

NP0170855

Secondary Accession Numbers

None

Natural Product Identification

Common Name

stipitatonic acid

Description

Stipitatonic acid, also known as stipitatonate, belongs to the class of organic compounds known as tropolones. Tropolones are compounds containing tropone ring with a hydroxyl group at ring position 2. stipitatonic acid is found in Talaromyces stipitatus. Stipitatonic acid is a moderately basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241500192D          

 15 16  0  0  0  0            999 V2000
    2.5000    0.1378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856    0.7828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1813    0.5992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5363    1.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5363    1.9386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1813    2.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856    2.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3436    1.5261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1686    1.5261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9977    3.2573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2483    2.1935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5033    2.9781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7333    1.5261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2483    0.8586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5033    0.0740    0.0000 O   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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  2  0  0  0  0
  6 10  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0170855

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(=O)C(O)=CC2=C1C(=O)OC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H4O6/c10-4-1-3-7(6(12)2-5(4)11)9(14)15-8(3)13/h1-2,12H,(H,10,11)

> <INCHI_KEY>
IECSWTFJOUGQFO-UHFFFAOYSA-N

> <FORMULA>
C9H4O6

> <MOLECULAR_WEIGHT>
208.125

> <EXACT_MASS>
208.000787849

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
17.131420937575918

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,7-dihydroxy-1H,3H,6H-cyclohepta[c]furan-1,3,6-trione

> <ALOGPS_LOGP>
-0.18

> <JCHEM_LOGP>
0.15943009033333327

> <ALOGPS_LOGS>
-1.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.459539639872315

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.509059062740023

> <JCHEM_PKA_STRONGEST_BASIC>
2.159756817316124

> <JCHEM_POLAR_SURFACE_AREA>
100.9

> <JCHEM_REFRACTIVITY>
48.80430000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.19e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
stipitatonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  O   UNK     0       4.667   0.257   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.706   1.461   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.205   1.119   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.001   2.079   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.001   3.619   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.205   4.579   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.706   4.236   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.375   2.849   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.915   2.849   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.862   6.080   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.464   4.095   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.939   5.559   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.369   2.849   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.464   1.603   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.939   0.138   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    2    9                                                  
CONECT    9    8                                                            
CONECT   10    6                                                            
CONECT   11    5   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    4   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Value	Source
3,6-Dihydroxy-5-oxo-1,3,6-cycloheptatriene-1,2-dicarboxylic anhydride	ChEBI
3,6-Dihydroxy-5-oxocyclohepta-1,3,6-triene-1,2-dicarboxylic anhydride	ChEBI
Stipitatonate	ChEBI

Chemical Formula

C₉H₄O₆

Average Mass

208.1250 Da

Monoisotopic Mass

208.00079 Da

IUPAC Name

4,7-dihydroxy-1H,3H,6H-cyclohepta[c]furan-1,3,6-trione

Traditional Name

stipitatonic acid

CAS Registry Number

Not Available

SMILES

OC1=CC(=O)C(O)=CC2=C1C(=O)OC2=O

InChI Identifier

InChI=1S/C9H4O6/c10-4-1-3-7(6(12)2-5(4)11)9(14)15-8(3)13/h1-2,12H,(H,10,11)

InChI Key

IECSWTFJOUGQFO-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, 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
Talaromyces stipitatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tropolones. Tropolones are compounds containing tropone ring with a hydroxyl group at ring position 2.

Kingdom

Organic compounds

Super Class

Hydrocarbon derivatives

Class

Tropones

Sub Class

Tropolones

Direct Parent

Tropolones

Alternative Parents

Substituents

Tropolone
Dicarboxylic acid or derivatives
Vinylogous acid
Carboxylic acid anhydride
Cyclic ketone
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cyclic dicarboxylic anhydride (CHEBI:16445 )
cycloheptafuran (CHEBI:16445 )

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	-0.18	ALOGPS
logP	0.16	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	5.51	ChemAxon
pKa (Strongest Basic)	2.16	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	48.8 m³·mol⁻¹	ChemAxon
Polarizability	17.13 Å³	ChemAxon
Number of Rings	2	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

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

C02080

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

16445

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for stipitatonic acid (NP0170855)

MOL for NP0170855 (stipitatonic acid)

3D MOL for NP0170855 (stipitatonic acid)

3D SDF for NP0170855 (stipitatonic acid)

3D-SDF for NP0170855 (stipitatonic acid)

PDB for NP0170855 (stipitatonic acid)

3D PDB for NP0170855 (stipitatonic acid)

SMILES for NP0170855 (stipitatonic acid)

INCHI for NP0170855 (stipitatonic acid)

Structure for NP0170855 (stipitatonic acid)

3D Structure for NP0170855 (stipitatonic acid)