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Showing NP-Card for Phyllostine (NP0140253)

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Record Information
Version2.0
Created at2022-06-29 21:16:26 UTC
Updated at2022-06-29 21:16:26 UTC
NP-MRD IDNP0140253
Secondary Accession NumbersNone
Natural Product Identification
Common NamePhyllostine
DescriptionPhyllostine belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. Phyllostine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Phyllostine is found in Epicoccum sorghinum, Ophiosphaerella herpotricha, Penicillium solitum, Penicillium urticae and Pseudopenicillium megasporum. Phyllostine was first documented in 1989 (PMID: 2605253). Based on a literature review a small amount of articles have been published on phyllostine (PMID: 28441516) (PMID: 31696600) (PMID: 23678814) (PMID: 22312735).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0140253 (Phyllostine)


  Mrv1652306292223162D          

 11 12  0  0  1  0            999 V2000
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  6  9  1  6  0  0  0
  5  9  1  6  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
Download

3D MOL for NP0140253 (Phyllostine)

     RDKit          3D

 17 18  0  0  0  0  0  0  0  0999 V2000
   -2.2005    2.2258   -0.3256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5449    1.1923    0.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1167    1.2845    0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6337    0.2330    0.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1097    0.2320    0.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7347    0.0019   -0.9304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0026   -0.9595   -0.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6459   -1.7063   -1.3085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3892   -1.2806   -0.0954 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4501   -0.9098   -0.8892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2273   -0.0917    0.2174 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3180    2.2001    0.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643   -0.5467    1.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3883    1.2232    0.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2556   -0.8352   -0.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4927   -2.1166    0.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0261   -0.1464    0.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  2 11  1  0
 11 10  1  0
 10  9  1  0
  9  7  1  0
  7  8  2  0
  7  4  1  0
  9 11  1  0
  6 15  1  0
  5 13  1  0
  5 14  1  0
  3 12  1  0
 11 17  1  1
  9 16  1  1
M  END
Download

3D SDF for NP0140253 (Phyllostine)


  Mrv1652306292223162D          

 11 12  0  0  1  0            999 V2000
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  6  9  1  6  0  0  0
  5  9  1  6  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0140253

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1=CC(=O)[C@H]2O[C@H]2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H6O4/c8-2-3-1-4(9)6-7(11-6)5(3)10/h1,6-8H,2H2/t6-,7+/m1/s1

> <INCHI_KEY>
PLELZLHJHUZIGY-RQJHMYQMSA-N

> <FORMULA>
C7H6O4

> <MOLECULAR_WEIGHT>
154.121

> <EXACT_MASS>
154.026608673

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.504029247523187

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,6S)-3-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione

> <ALOGPS_LOGP>
-0.70

> <JCHEM_LOGP>
-0.487288841

> <ALOGPS_LOGS>
0.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.389419946671673

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.885414086043241

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8363984410088703

> <JCHEM_POLAR_SURFACE_AREA>
66.9

> <JCHEM_REFRACTIVITY>
35.2569

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.57e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,6S)-3-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0140253 (Phyllostine)

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PDB for NP0140253 (Phyllostine)
HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.001   5.390   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    9                                                  
CONECT    6    5    7    9                                                  
CONECT    7    6    1    8                                                  
CONECT    8    7                                                            
CONECT    9    6    5                                                       
CONECT   10    2   11                                                       
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

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3D PDB for NP0140253 (Phyllostine)
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SMILES for NP0140253 (Phyllostine)
OCC1=CC(=O)[C@H]2O[C@H]2C1=O
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INCHI for NP0140253 (Phyllostine)
InChI=1S/C7H6O4/c8-2-3-1-4(9)6-7(11-6)5(3)10/h1,6-8H,2H2/t6-,7+/m1/s1
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View in JSmol
Synonyms
ValueSource
(-)-PhyllostineChEBI
5,6-EpoxygentisylquinoneChEBI
EpoxygentisylquinoneChEBI
Chemical FormulaC7H6O4
Average Mass154.1210 Da
Monoisotopic Mass154.02661 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
OCC1=CC(=O)[C@H]2O[C@H]2C1=O
InChI Identifier
InChI=1S/C7H6O4/c8-2-3-1-4(9)6-7(11-6)5(3)10/h1,6-8H,2H2/t6-,7+/m1/s1
InChI KeyPLELZLHJHUZIGY-RQJHMYQMSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Epicoccum sorghinumLOTUS Database
Ophiosphaerella herpotrichaLOTUS Database
Penicillium solitumLOTUS Database
Penicillium urticaeLOTUS Database
Pseudopenicillium megasporumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentCyclohexenones  
Alternative Parents
Substituents
  • Cyclohexenone
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Ether
    • 

  • Oxirane
    • 

  • Dialkyl ether
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • Alcohol
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID147548  
KEGG Compound IDNot Available
BioCyc IDCPD-16724  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound168678  
PDB IDNot Available
ChEBI ID145110  
Good Scents IDNot Available
References
General References
  1. Ibrahim A, Sorensen D, Jenkins HA, Ejim L, Capretta A, Sumarah MW: Epoxynemanione A, nemanifuranones A-F, and nemanilactones A-C, from Nemania serpens, an endophytic fungus isolated from Riesling grapevines. Phytochemistry. 2017 Aug;140:16-26. doi: 10.1016/j.phytochem.2017.04.009. Epub 2017 Apr 22. [PubMed:28441516  ] 
  2. Ratnaweera PB, M Jayasundara JMN, Herath HHMSD, Williams DE, Rajapaksha SU, Nishantha KMDWP, de Silva ED, Andersen RJ: Antifeedant, contact toxicity and oviposition deterrent effects of phyllostine acetate and phyllostine isolated from the endophytic fungus Diaporthe miriciae against Plutella xylostella larvae. Pest Manag Sci. 2020 Apr;76(4):1541-1548. doi: 10.1002/ps.5673. Epub 2019 Dec 2. [PubMed:31696600  ] 
  3. Flewelling AJ, Johnson JA, Gray CA: Antimicrobials from the marine algal endophyte Penicillium sp. Nat Prod Commun. 2013 Mar;8(3):373-4. [PubMed:23678814  ] 
  4. Hussain H, Tchimene MK, Ahmed I, Meier K, Steinert M, Draeger S, Schulz B, Krohn K: Antimicrobial chemical constituents from the endophytic fungus Phomopsis sp. from Notobasis syriaca. Nat Prod Commun. 2011 Dec;6(12):1905-6. [PubMed:22312735  ] 
  5. Priest JW, Light RJ: Patulin biosynthesis: epoxidation of toluquinol and gentisyl alcohol by particulate preparations from Penicillium patulum. Biochemistry. 1989 Nov 14;28(23):9192-200. doi: 10.1021/bi00449a035. [PubMed:2605253  ]