NP-MRD: Showing NP-Card for Desoxypatulinic acid (NP0021526)

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Record Information

Version

2.0

Created at

2021-01-06 06:49:10 UTC

Updated at

2021-07-15 17:36:35 UTC

NP-MRD ID

NP0021526

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Desoxypatulinic acid

Provided By

NPAtlas

Description

Deoxypatulinic acid is also known as deoxypatulinate. Desoxypatulinic acid is found in Penicillium and Penicillium solitum. Desoxypatulinic acid was first documented in 1972 (PMID: 5087059). Based on a literature review very few articles have been published on Deoxypatulinic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105163D          

 19 19  0  0  0  0            999 V2000
    1.8016   -0.1964    1.6218 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3833   -0.2225    0.5093 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7679   -0.2133    0.5244 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6072   -0.2615   -0.7609 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1477   -0.2617   -0.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6651   -1.2415   -0.7751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0254   -1.2513   -0.4632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6296    0.0110   -0.2061 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7836    0.6353    0.9126 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4313    0.8461    0.3299 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1802    1.9333    0.4812 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2070    0.6952    0.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7905    0.7163   -1.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8637   -1.0910   -1.4115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2112   -2.0657   -1.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6809   -0.0502    0.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4262    0.6493   -1.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6653   -0.1764    1.6726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2305    1.5447    1.3128 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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  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  1  0  0  0  0
 10 11  2  0  0  0  0
 10  5  1  0  0  0  0
  3 12  1  0  0  0  0
  4 13  1  0  0  0  0
  4 14  1  0  0  0  0
  6 15  1  0  0  0  0
  8 16  1  0  0  0  0
  8 17  1  0  0  0  0
  9 18  1  0  0  0  0
  9 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021526

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H8O4/c8-6-1-2-11-4-5(6)3-7(9)10/h4H,1-3H2,(H,9,10)

> <INCHI_KEY>
NDEBBGKFXQDNLC-UHFFFAOYSA-N

> <FORMULA>
C7H8O4

> <MOLECULAR_WEIGHT>
156.137

> <EXACT_MASS>
156.042258738

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
14.264635804402275

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(4-oxo-3,4-dihydro-2H-pyran-5-yl)acetic acid

> <ALOGPS_LOGP>
-0.10

> <JCHEM_LOGP>
-0.15679311800000018

> <ALOGPS_LOGS>
-0.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.19144819656085

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9828587259080788

> <JCHEM_PKA_STRONGEST_BASIC>
-4.761028953122281

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
36.3352

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.30e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4-oxo-5,6-dihydropyran-3-yl)acetic 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  O   UNK     0       1.802  -0.196   1.622  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.383  -0.223   0.509  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.768  -0.213   0.524  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.607  -0.262  -0.761  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.148  -0.262  -0.421  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.665  -1.242  -0.775  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.025  -1.251  -0.463  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.630   0.011  -0.206  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.784   0.635   0.913  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.431   0.846   0.330  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.180   1.933   0.481  0.00  0.00           O+0
HETATM   12  H   UNK     0       4.207   0.695   0.340  0.00  0.00           H+0
HETATM   13  H   UNK     0       1.791   0.716  -1.268  0.00  0.00           H+0
HETATM   14  H   UNK     0       1.864  -1.091  -1.412  0.00  0.00           H+0
HETATM   15  H   UNK     0      -0.211  -2.066  -1.339  0.00  0.00           H+0
HETATM   16  H   UNK     0      -3.681  -0.050   0.053  0.00  0.00           H+0
HETATM   17  H   UNK     0      -2.426   0.649  -1.113  0.00  0.00           H+0
HETATM   18  H   UNK     0      -1.665  -0.176   1.673  0.00  0.00           H+0
HETATM   19  H   UNK     0      -2.231   1.545   1.313  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2   12                                                       
CONECT    4    2    5   13   14                                             
CONECT    5    4    6   10                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   16   17                                             
CONECT    9    8   10   18   19                                             
CONECT   10    9   11    5                                                  
CONECT   11   10                                                            
CONECT   12    3                                                            
CONECT   13    4                                                            
CONECT   14    4                                                            
CONECT   15    6                                                            
CONECT   16    8                                                            
CONECT   17    8                                                            
CONECT   18    9                                                            
CONECT   19    9                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Deoxypatulinate	Generator
2-(4-oxo-3,4-Dihydro-2H-pyran-5-yl)acetate	Generator

Chemical Formula

C₇H₈O₄

Average Mass

156.1370 Da

Monoisotopic Mass

156.04226 Da

IUPAC Name

2-(4-oxo-3,4-dihydro-2H-pyran-5-yl)acetic acid

Traditional Name

(4-oxo-5,6-dihydropyran-3-yl)acetic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CC1=COCCC1=O

InChI Identifier

InChI=1S/C7H8O4/c8-6-1-2-11-4-5(6)3-7(9)10/h4H,1-3H2,(H,9,10)

InChI Key

NDEBBGKFXQDNLC-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	NPAtlas	5087059
Penicillium solitum	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Penicillium patulam	KNApSAcK Database	22123792
Penicillium urticae strain No 562	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as dihydropyranones. These are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Dihydropyranones

Alternative Parents

Substituents

Dihydropyranone
Vinylogous ester
Cyclic ketone
Ketone
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	-0.1	ALOGPS
logP	-0.16	ChemAxon
logS	-0.68	ALOGPS
pKa (Strongest Acidic)	3.98	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	36.34 m³·mol⁻¹	ChemAxon
Polarizability	14.26 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

NPA003893

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00024002

Chemspider ID

32740642

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71437500

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Scott PM, Kennedy B, Van Walbeek W: Desoxypatulinic acid from a patulin-producing strain of Penicillium patulum. Experientia. 1972 Oct 15;28(10):1252. doi: 10.1007/BF01946206. [PubMed:5087059 ]

Showing NP-Card for Desoxypatulinic acid (NP0021526)

MOL for NP0021526 (Desoxypatulinic acid)

3D MOL for NP0021526 (Desoxypatulinic acid)

3D SDF for NP0021526 (Desoxypatulinic acid)

3D-SDF for NP0021526 (Desoxypatulinic acid)

PDB for NP0021526 (Desoxypatulinic acid)

3D PDB for NP0021526 (Desoxypatulinic acid)

SMILES for NP0021526 (Desoxypatulinic acid)

INCHI for NP0021526 (Desoxypatulinic acid)

Structure for NP0021526 (Desoxypatulinic acid)

3D Structure for NP0021526 (Desoxypatulinic acid)