NP-MRD: Showing NP-Card for Penipratynolene (NP0005086)

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Record Information

Version

2.0

Created at

2020-12-09 02:26:00 UTC

Updated at

2021-07-15 16:51:00 UTC

NP-MRD ID

NP0005086

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Penipratynolene

Provided By

NPAtlas

Description

Penipratynolene is found in Penicillium and Penicillium bilaiae. Penipratynolene was first documented in 2004 (PMID: 14745197). Based on a literature review very few articles have been published on Penipratynolene (PMID: 26243556).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118163D          

 28 28  0  0  0  0            999 V2000
   -4.8869   -0.5089    1.6320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6119   -0.3533    0.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2680   -0.1456   -0.9515 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3471    1.2302   -1.2438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7889   -0.5187   -1.1183 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0816    0.2842   -0.1916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7025    0.1757   -0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0242   -0.7150   -0.9162 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3446   -0.8446   -0.8494 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0411   -0.0601    0.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4866   -0.1685    0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1309   -0.9659   -0.5673 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1766    0.6033    1.0492 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5974    0.5374    1.1890 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3789    0.8374    0.8810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004    0.9533    0.7985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1230   -0.6360    2.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8933   -0.7355   -1.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7667    1.4693   -2.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7171   -1.5813   -0.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4643   -0.3783   -2.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5869   -1.3212   -1.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8780   -1.5350   -1.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9338   -0.3373    0.6037 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8440    0.3514    2.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0591    1.4953    0.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9305    1.4407    1.5803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5389    1.6460    1.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  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
 10 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
 10 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16  7  1  0  0  0  0
  1 17  1  0  0  0  0
  3 18  1  6  0  0  0
  4 19  1  0  0  0  0
  5 20  1  0  0  0  0
  5 21  1  0  0  0  0
  8 22  1  0  0  0  0
  9 23  1  0  0  0  0
 14 24  1  0  0  0  0
 14 25  1  0  0  0  0
 14 26  1  0  0  0  0
 15 27  1  0  0  0  0
 16 28  1  0  0  0  0
M  END


  Mrv1652306242118163D          

 28 28  0  0  0  0            999 V2000
   -4.8869   -0.5089    1.6320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6119   -0.3533    0.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2680   -0.1456   -0.9515 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3471    1.2302   -1.2438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7889   -0.5187   -1.1183 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0816    0.2842   -0.1916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7025    0.1757   -0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0242   -0.7150   -0.9162 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3446   -0.8446   -0.8494 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0411   -0.0601    0.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4866   -0.1685    0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1309   -0.9659   -0.5673 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1766    0.6033    1.0492 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5974    0.5374    1.1890 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3789    0.8374    0.8810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004    0.9533    0.7985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1230   -0.6360    2.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8933   -0.7355   -1.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7667    1.4693   -2.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7171   -1.5813   -0.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4643   -0.3783   -2.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5869   -1.3212   -1.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8780   -1.5350   -1.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9338   -0.3373    0.6037 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8440    0.3514    2.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0591    1.4953    0.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9305    1.4407    1.5803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5389    1.6460    1.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  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
 10 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
 10 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16  7  1  0  0  0  0
  1 17  1  0  0  0  0
  3 18  1  6  0  0  0
  4 19  1  0  0  0  0
  5 20  1  0  0  0  0
  5 21  1  0  0  0  0
  8 22  1  0  0  0  0
  9 23  1  0  0  0  0
 14 24  1  0  0  0  0
 14 25  1  0  0  0  0
 14 26  1  0  0  0  0
 15 27  1  0  0  0  0
 16 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0005086

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]([H])(C#C[H])C([H])([H])OC1=C([H])C([H])=C(C([H])=C1[H])C(=O)OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H12O4/c1-3-10(13)8-16-11-6-4-9(5-7-11)12(14)15-2/h1,4-7,10,13H,8H2,2H3/t10-/m1/s1

> <INCHI_KEY>
XHEHRJGOTYDGPW-SNVBAGLBSA-N

> <FORMULA>
C12H12O4

> <MOLECULAR_WEIGHT>
220.224

> <EXACT_MASS>
220.073558866

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
23.00400206815759

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 4-{[(2R)-2-hydroxybut-3-yn-1-yl]oxy}benzoate

> <ALOGPS_LOGP>
1.29

> <JCHEM_LOGP>
1.416799618333334

> <ALOGPS_LOGS>
-3.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.930667759734408

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7039259218921687

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
58.089200000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 4-{[(2R)-2-hydroxybut-3-yn-1-yl]oxy}benzoate

> <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      -4.887  -0.509   1.632  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.612  -0.353   0.467  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.268  -0.146  -0.952  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.347   1.230  -1.244  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.789  -0.519  -1.118  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.082   0.284  -0.192  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.703   0.176  -0.102  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.024  -0.715  -0.916  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.345  -0.845  -0.849  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.041  -0.060   0.057  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.487  -0.169   0.157  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.131  -0.966  -0.567  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.177   0.603   1.049  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.597   0.537   1.189  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.379   0.837   0.881  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.000   0.953   0.799  0.00  0.00           C+0
HETATM   17  H   UNK     0      -5.123  -0.636   2.664  0.00  0.00           H+0
HETATM   18  H   UNK     0      -4.893  -0.736  -1.626  0.00  0.00           H+0
HETATM   19  H   UNK     0      -3.767   1.469  -2.015  0.00  0.00           H+0
HETATM   20  H   UNK     0      -2.717  -1.581  -0.773  0.00  0.00           H+0
HETATM   21  H   UNK     0      -2.464  -0.378  -2.155  0.00  0.00           H+0
HETATM   22  H   UNK     0      -0.587  -1.321  -1.620  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.878  -1.535  -1.480  0.00  0.00           H+0
HETATM   24  H   UNK     0       5.934  -0.337   0.604  0.00  0.00           H+0
HETATM   25  H   UNK     0       5.844   0.351   2.259  0.00  0.00           H+0
HETATM   26  H   UNK     0       6.059   1.495   0.840  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.931   1.441   1.580  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.539   1.646   1.431  0.00  0.00           H+0
CONECT    1    2   17                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5   18                                             
CONECT    4    3   19                                                       
CONECT    5    3    6   20   21                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   16                                                  
CONECT    8    7    9   22                                                  
CONECT    9    8   10   23                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   24   25   26                                             
CONECT   15   10   16   27                                                  
CONECT   16   15    7   28                                                  
CONECT   17    1                                                            
CONECT   18    3                                                            
CONECT   19    4                                                            
CONECT   20    5                                                            
CONECT   21    5                                                            
CONECT   22    8                                                            
CONECT   23    9                                                            
CONECT   24   14                                                            
CONECT   25   14                                                            
CONECT   26   14                                                            
CONECT   27   15                                                            
CONECT   28   16                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   56    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Methyl (2'r)-4-(2'-hydroxy-3'-butynoxy)benzoate	MeSH
Methyl 4-(2'-hydroxy-3'-butynoxy)benzoate	MeSH
Methyl 4-{[(2R)-2-hydroxybut-3-yn-1-yl]oxy}benzoic acid	Generator

Chemical Formula

C₁₂H₁₂O₄

Average Mass

220.2240 Da

Monoisotopic Mass

220.07356 Da

IUPAC Name

methyl 4-{[(2R)-2-hydroxybut-3-yn-1-yl]oxy}benzoate

Traditional Name

methyl 4-{[(2R)-2-hydroxybut-3-yn-1-yl]oxy}benzoate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC=C(OC[C@H](O)C#C)C=C1

InChI Identifier

InChI=1S/C12H12O4/c1-3-10(13)8-16-11-6-4-9(5-7-11)12(14)15-2/h1,4-7,10,13H,8H2,2H3/t10-/m1/s1

InChI Key

XHEHRJGOTYDGPW-SNVBAGLBSA-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	14745197
Penicillium bilaiae	LOTUS Database	35616633

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	1.29	ALOGPS
logP	1.42	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	12.93	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	58.09 m³·mol⁻¹	ChemAxon
Polarizability	23 Å³	ChemAxon
Number of Rings	1	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

NPA013194

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

57539385

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71368208

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nakahara S, Kusano M, Fujioka S, Shimada A, Kimura Y: Penipratynolene, a novel nematicide from penicillium bilaiae Chalabuda. Biosci Biotechnol Biochem. 2004 Jan;68(1):257-9. doi: 10.1271/bbb.68.257. [PubMed:14745197 ]
Bu YY, Yamazaki H, Takahashi O, Kirikoshi R, Ukai K, Namikoshi M: Penicyrones A and B, an epimeric pair of alpha-pyrone-type polyketides produced by the marine-derived Penicillium sp. J Antibiot (Tokyo). 2016 Jan;69(1):57-61. doi: 10.1038/ja.2015.82. Epub 2015 Aug 5. [PubMed:26243556 ]

Showing NP-Card for Penipratynolene (NP0005086)

MOL for NP0005086 (Penipratynolene)

3D MOL for NP0005086 (Penipratynolene)

3D SDF for NP0005086 (Penipratynolene)

3D-SDF for NP0005086 (Penipratynolene)

PDB for NP0005086 (Penipratynolene)

3D PDB for NP0005086 (Penipratynolene)

SMILES for NP0005086 (Penipratynolene)

INCHI for NP0005086 (Penipratynolene)

Structure for NP0005086 (Penipratynolene)

3D Structure for NP0005086 (Penipratynolene)