NP-MRD: Showing NP-Card for Pyriculariol (NP0066333)

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Record Information

Version

1.0

Created at

2022-04-28 10:37:00 UTC

Updated at

2022-04-28 10:37:00 UTC

NP-MRD ID

NP0066333

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pyriculariol

Description

Pyriculariol belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. Pyriculariol is found in Pyricularia oryzae. It was first documented in 2017 (PMID: 27902426). Based on a literature review a small amount of articles have been published on pyriculariol (PMID: 32913421) (PMID: 33577666) (PMID: 33577655).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 34  0  0  0  0  0  0  0  0999 V2000
   -5.5927   -0.6687    0.6824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1795   -0.1983    0.9084 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1067    0.8191    1.8521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6509    0.2900   -0.4467 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7197   -0.7183   -1.3942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3042    0.8256   -0.2491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2472    0.0529   -0.3766 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1232    0.5744   -0.1811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1682   -0.2122   -0.3125 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5556    0.1748   -0.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8058    1.4900    0.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0983    1.9672    0.3575 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1216    1.1038    0.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8966   -0.2531   -0.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9993   -1.0502   -0.2572 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167   -0.7215   -0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3139   -2.0929   -0.6452 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2203   -2.9336   -0.7966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5509   -1.4577   -0.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0046   -1.0324    1.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1578    0.2290    0.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5207   -1.0398    1.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2154    0.8749    2.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3277    1.1110   -0.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9152   -0.6511   -1.9848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1409    1.8632    0.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3811   -0.9793   -0.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2861    1.6052    0.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9361   -1.2358   -0.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0427    2.2330    0.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2876    3.0170    0.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1483    1.4412    0.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0797   -1.9741   -0.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3150   -2.4532   -0.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 16 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  1
  3 23  1  0
  4 24  1  6
  5 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 15 33  1  0
 17 34  1  0
M  END


  Mrv1652304282212372D          

 18 18  0  0  1  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  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  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  6  0  0  0
 11 15  1  1  0  0  0
  4 16  1  0  0  0  0
 16 17  2  0  0  0  0
  3 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066333

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](O)[C@H](O)\C=C\C=C\C1=CC=CC(O)=C1C=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O4/c1-10(16)13(17)7-3-2-5-11-6-4-8-14(18)12(11)9-15/h2-10,13,16-18H,1H3/b5-2+,7-3+/t10-,13+/m0/s1

> <INCHI_KEY>
UPAHLPUINKDRNK-BZUCXLHXSA-N

> <FORMULA>
C14H16O4

> <MOLECULAR_WEIGHT>
248.278

> <EXACT_MASS>
248.104858995

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
26.71286175802965

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1E,3E,5R,6S)-5,6-dihydroxyhepta-1,3-dien-1-yl]-6-hydroxybenzaldehyde

> <ALOGPS_LOGP>
1.63

> <JCHEM_LOGP>
2.1882045009999995

> <ALOGPS_LOGS>
-3.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.743594987563764

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.345004136815119

> <JCHEM_PKA_STRONGEST_BASIC>
-3.034380612065087

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
72.4573

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.82e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1E,3E,5R,6S)-5,6-dihydroxyhepta-1,3-dien-1-yl]-6-hydroxybenzaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.668   8.470   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.667   9.240   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5   16                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   11                                                            
CONECT   16    4   17                                                       
CONECT   17   16                                                            
CONECT   18    3                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Value	Source
(-)-2-[(1E,3E,5R,6S)-5,6-Dihydroxyhepta-1,3-dien-1-yl]-6-hydroxybenzaldehyde	ChEBI
(-)-Pyriculariol	ChEBI

Chemical Formula

C₁₄H₁₆O₄

Average Mass

248.2780 Da

Monoisotopic Mass

248.10486 Da

IUPAC Name

2-[(1E,3E,5R,6S)-5,6-dihydroxyhepta-1,3-dien-1-yl]-6-hydroxybenzaldehyde

Traditional Name

2-[(1E,3E,5R,6S)-5,6-dihydroxyhepta-1,3-dien-1-yl]-6-hydroxybenzaldehyde

CAS Registry Number

Not Available

SMILES

C[C@H](O)[C@H](O)\C=C\C=C\C1=CC=CC(O)=C1C=O

InChI Identifier

InChI=1S/C14H16O4/c1-10(16)13(17)7-3-2-5-11-6-4-8-14(18)12(11)9-15/h2-10,13,16-18H,1H3/b5-2+,7-3+/t10-,13+/m0/s1

InChI Key

UPAHLPUINKDRNK-BZUCXLHXSA-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
Pyricularia oryzae	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Fatty alcohols

Alternative Parents

Substituents

Fatty alcohol
Hydroxybenzaldehyde
Benzaldehyde
Benzoyl
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aryl-aldehyde
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
1,2-diol
Secondary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aldehyde
Alcohol
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	1.63	ALOGPS
logP	2.19	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	8.35	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	72.46 m³·mol⁻¹	ChemAxon
Polarizability	26.71 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00023717

Chemspider ID

76963378

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44191151

PDB ID

Not Available

ChEBI ID

142636

Good Scents ID

Not Available

References

General References

Kiyota H: Synthetic studies of biologically active natural products contributing to pesticide development. J Pestic Sci. 2020 Aug 20;45(3):177-183. doi: 10.1584/jpestics.J20-03. [PubMed:32913421 ]
Furuyama Y, Motoyama T, Nogawa T, Hayashi T, Hirota H, Kiyota H, Kamakura T, Osada H: Controlling the production of phytotoxin pyriculol in Pyricularia oryzae by aldehyde reductase. Biosci Biotechnol Biochem. 2021 Jan 7;85(1):126-133. doi: 10.1093/bbb/zbaa035. [PubMed:33577666 ]
Jacob S, Grotsch T, Foster AJ, Schuffler A, Rieger PH, Sandjo LP, Liermann JC, Opatz T, Thines E: Unravelling the biosynthesis of pyriculol in the rice blast fungus Magnaporthe oryzae. Microbiology (Reading). 2017 Apr;163(4):541-553. doi: 10.1099/mic.0.000396. Epub 2017 Apr 6. [PubMed:27902426 ]
Nagashima Y, Sasaki A, Hiraoka R, Onoda Y, Tanaka K, Wang ZY, Kuwana A, Sato Y, Suzuki Y, Izumi M, Kuwahara S, Nukina M, Kiyota H: Synthesis of (12R,13S)-pyriculariol and (12R,13S)-dihydropyriculariol revealed that the rice blast fungus, Pyricularia oryzae, produces these phytotoxins as racemates. Biosci Biotechnol Biochem. 2021 Jan 7;85(1):134-142. doi: 10.1093/bbb/zbaa002. [PubMed:33577655 ]

Showing NP-Card for Pyriculariol (NP0066333)

MOL for NP0066333 (Pyriculariol)

3D MOL for NP0066333 (Pyriculariol)

3D SDF for NP0066333 (Pyriculariol)

3D-SDF for NP0066333 (Pyriculariol)

PDB for NP0066333 (Pyriculariol)

3D PDB for NP0066333 (Pyriculariol)

SMILES for NP0066333 (Pyriculariol)

INCHI for NP0066333 (Pyriculariol)

Structure for NP0066333 (Pyriculariol)

3D Structure for NP0066333 (Pyriculariol)