NP-MRD: Showing NP-Card for Tutin (NP0051972)

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Record Information

Version

2.0

Created at

2022-04-27 23:10:41 UTC

Updated at

2022-04-27 23:10:41 UTC

NP-MRD ID

NP0051972

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tutin

Description

Tutin belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Thus, tutin is considered to be an isoprenoid. Tutin is found in Coriaria angustissima, Coriaria japonica , Coriaria microphylla, Coriaria sinica, Picrodendron baccatum, Scurrula parasitica and Toxicodendron capense. Tutin was first documented in 2014 (PMID: 25084484). Based on a literature review a significant number of articles have been published on Tutin (PMID: 35206738) (PMID: 34839979) (PMID: 33835527) (PMID: 33016067) (PMID: 29649198) (PMID: 29504746).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 43  0  0  0  0  0  0  0  0999 V2000
    2.7546    1.7248    0.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6787    0.4138    0.2662 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5930   -0.3576    1.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7689   -0.1992   -0.6547 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8244   -1.2530   -0.2717 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1694   -1.4091   -1.6474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0634   -2.5012   -2.1625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0361   -0.0912   -2.0460 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7478    0.8075   -1.2254 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0590    1.3174   -0.0774 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6710    2.5363   -0.3368 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0927    0.2518    0.2698 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7987    0.7174    1.5250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3185   -1.0015    0.6211 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0827   -1.1429    1.9679 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3891   -2.0520    0.2631 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6847   -1.8416    0.6612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1994   -1.5425   -0.7348 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0332   -0.0377   -0.8193 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6387    0.7187   -1.7942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3947    0.5467   -0.6155 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1481    2.3916   -0.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4151    2.2312    1.1218 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6600   -1.4182    0.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2564   -0.2373    2.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6229    0.0541    1.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2838   -0.5732   -1.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2935   -2.2218    0.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2308    1.5718   -1.8364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4742    1.4493    0.8881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3631    3.2648    0.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9254    1.8388    1.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2500    0.4319    2.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8277    0.3061    1.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8412   -1.5892    2.4337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0367   -3.1048    0.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7895   -2.0608   -1.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0254    0.2577   -2.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4007    1.8033   -1.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  3
  2  4  1  0
  4  9  1  0
  9  8  1  0
  8  6  1  0
  6  7  2  0
  6  5  1  0
  5 14  1  0
 14 15  1  1
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 12  1  0
 12 13  1  1
 12 10  1  0
 10 11  1  0
  5  4  1  0
 12 14  1  0
 10  9  1  0
 18 16  1  0
 19 21  1  1
  3 24  1  0
  3 25  1  0
  3 26  1  0
  1 22  1  0
  1 23  1  0
  4 27  1  6
  9 29  1  6
  5 28  1  1
 15 35  1  0
 16 36  1  6
 18 37  1  6
 20 38  1  0
 20 39  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 10 30  1  1
 11 31  1  0
M  END

  Mrv1652304282201102D          

 21 25  0  0  1  0            999 V2000
    0.3188    0.4705    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1036    0.2160    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4169    1.1186    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2686    2.0624    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4512    1.9512    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0285    1.2427    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7760    1.4257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8504    2.2474    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0920    2.5721    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7525    3.0665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0421    0.6448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5853    1.2658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5139    0.6210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7406    2.7237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8653    1.4927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6375    1.7830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7919    0.6709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2386    1.0452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8984    1.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5859    0.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2509   -0.1262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  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
  5  9  1  0  0  0  0
  9 10  1  6  0  0  0
  8 10  1  6  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  6  0  0  0
  6 13  1  6  0  0  0
  5 14  1  6  0  0  0
  4 15  1  1  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  2 17  1  1  0  0  0
  3 18  1  6  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  1 21  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0051972

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@@H]1[C@H]2OC(=O)[C@@H]1[C@]1(O)[C@H]3O[C@H]3[C@]3(CO3)[C@]1(C)[C@@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O6/c1-5(2)6-7-12(17)20-8(6)9(16)13(3)14(4-19-14)10-11(21-10)15(7,13)18/h6-11,16,18H,1,4H2,2-3H3/t6-,7+,8+,9+,10+,11-,13-,14+,15-/m0/s1

> <INCHI_KEY>
CCAZWUJBLXKBAY-ULZPOIKGSA-N

> <FORMULA>
C15H18O6

> <MOLECULAR_WEIGHT>
294.303

> <EXACT_MASS>
294.1103383

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
28.05085406715388

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'S,2R,2'R,3'S,5'R,7'R,8'S,9'R,12'R)-2',8'-dihydroxy-7'-methyl-12'-(prop-1-en-2-yl)-4',10'-dioxaspiro[oxirane-2,6'-tetracyclo[7.2.1.0^{2,7}.0^{3,5}]dodecane]-11'-one

> <ALOGPS_LOGP>
-0.11

> <JCHEM_LOGP>
-0.6623660140000003

> <ALOGPS_LOGS>
-0.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.691762241604096

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.692023026665279

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4424907047101714

> <JCHEM_POLAR_SURFACE_AREA>
91.82000000000001

> <JCHEM_REFRACTIVITY>
67.4668

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.87e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2R,2'R,3'S,5'R,7'R,8'S,9'R,12'R)-2',8'-dihydroxy-7'-methyl-12'-(prop-1-en-2-yl)-4',10'-dioxaspiro[oxirane-2,6'-tetracyclo[7.2.1.0^{2,7}.0^{3,5}]dodecane]-11'-one

> <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       0.595   0.878   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.060   0.403   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.645   2.088   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.368   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.842   3.642   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.053   2.320   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.448   2.661   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.587   4.195   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.172   4.801   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.405   5.724   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.945   1.204   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.959   2.363   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.959   1.159   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.382   5.084   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.482   2.786   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.923   3.328   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.345   1.252   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.179   1.951   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.410   2.875   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.827   0.554   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.468  -0.236   0.000  0.00  0.00           O+0
CONECT    1    2    6   21                                                  
CONECT    2    1    3   17                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5   15                                                  
CONECT    5    4    6    9   14                                             
CONECT    6    5    1    7   13                                             
CONECT    7    6    8   11   12                                             
CONECT    8    7    9   10                                                  
CONECT    9    8    5   10                                                  
CONECT   10    9    8                                                       
CONECT   11    7   12                                                       
CONECT   12   11    7                                                       
CONECT   13    6                                                            
CONECT   14    5                                                            
CONECT   15    4   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    2                                                       
CONECT   18    3   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21    1                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   50    0
END

View in JSmol

Synonyms

Value	Source
2a,3a-Epoxy-3a,4a,5,6,7,7a-hexahydro-3a alpha,6 beta,7 beta-trihydroxy-5 alpha-isopropyl-7a alpha- methylspiro(indan-1,2'-oxirane) gamma-lactone	MeSH

Chemical Formula

C₁₅H₁₈O₆

Average Mass

294.3030 Da

Monoisotopic Mass

294.11034 Da

IUPAC Name

(1'S,2R,2'R,3'S,5'R,7'R,8'S,9'R,12'R)-2',8'-dihydroxy-7'-methyl-12'-(prop-1-en-2-yl)-4',10'-dioxaspiro[oxirane-2,6'-tetracyclo[7.2.1.0^{2,7}.0^{3,5}]dodecane]-11'-one

Traditional Name

(1'S,2R,2'R,3'S,5'R,7'R,8'S,9'R,12'R)-2',8'-dihydroxy-7'-methyl-12'-(prop-1-en-2-yl)-4',10'-dioxaspiro[oxirane-2,6'-tetracyclo[7.2.1.0^{2,7}.0^{3,5}]dodecane]-11'-one

CAS Registry Number

Not Available

SMILES

CC(=C)[C@@H]1[C@H]2OC(=O)[C@@H]1[C@]1(O)[C@H]3O[C@H]3[C@]3(CO3)[C@]1(C)[C@@H]2O

InChI Identifier

InChI=1S/C15H18O6/c1-5(2)6-7-12(17)20-8(6)9(16)13(3)14(4-19-14)10-11(21-10)15(7,13)18/h6-11,16,18H,1,4H2,2-3H3/t6-,7+,8+,9+,10+,11-,13-,14+,15-/m0/s1

InChI Key

CCAZWUJBLXKBAY-ULZPOIKGSA-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
Coriaria angustissima	Plant	KNApSAcK
Coriaria japonica	Plant	KNApSAcK
Coriaria microphylla	LOTUS Database	35616633
Coriaria sinica	Plant	KNApSAcK
Picrodendron baccatum	LOTUS Database	35616633
Scurrula parasitica	LOTUS Database	35616633
Toxicodendron capense	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Oxepane
Gamma butyrolactone
Oxane
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

gamma-lactone (CHEBI:9783 )
Sesquiterpenes (C09570 )
Tutinolide (C09570 )

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	-0.11	ALOGPS
logP	-0.66	ChemAxon
logS	-0.88	ALOGPS
pKa (Strongest Acidic)	12.69	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.82 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	67.47 m³·mol⁻¹	ChemAxon
Polarizability	28.05 Å³	ChemAxon
Number of Rings	5	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

C00003381

Chemspider ID

10252021

KEGG Compound ID

C09570

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tutin

METLIN ID

Not Available

PubChem Compound

75729

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1498371

References

General References

Papanikolaou NE, Kavallieratos NG, Iliopoulos V, Evergetis E, Skourti A, Nika EP, Haroutounian SA: Essential Oil Coating: Mediterranean Culinary Plants as Grain Protectants against Larvae and Adults of Tribolium castaneum and Trogoderma granarium. Insects. 2022 Feb 3;13(2). pii: insects13020165. doi: 10.3390/insects13020165. [PubMed:35206738 ]
Yan S, Wang K, Al Naggar Y, Vander Heyden Y, Zhao L, Wu L, Xue X: Natural plant toxins in honey: An ignored threat to human health. J Hazard Mater. 2022 Feb 15;424(Pt D):127682. doi: 10.1016/j.jhazmat.2021.127682. Epub 2021 Nov 6. [PubMed:34839979 ]
Li F, Cui J, Shaheen T, Tang G, Wang T, Woolfley T, Li M: Biocidal efficacy of tutin and its influence on immune cells and expression of growth-blocking and neuroglian peptides in Mythimna separata (Lepidoptera: Noctuidae). Arch Insect Biochem Physiol. 2021 May;107(1):e21767. doi: 10.1002/arch.21767. Epub 2021 Apr 9. [PubMed:33835527 ]
Olivon F, Retailleau P, Desrat S, Touboul D, Roussi F, Apel C, Litaudon M: Isolation of Picrotoxanes from Austrobuxus carunculatus Using Taxonomy-Based Molecular Networking. J Nat Prod. 2020 Oct 23;83(10):3069-3079. doi: 10.1021/acs.jnatprod.0c00636. Epub 2020 Oct 5. [PubMed:33016067 ]
Beasley M, Hood D, Anderson P, Reeve J, Slaughter RJ: Poisoning due to tutin in honey-a report of an outbreak in New Zealand. N Z Med J. 2018 Apr 13;131(1473):59-71. [PubMed:29649198 ]
Watkins OC, Joyce NI, Gould N, Perry NB: Glycosides of the Neurotoxin Tutin in Toxic Honeys Are from Coriaria arborea Phloem Sap, Not Insect Metabolism. J Nat Prod. 2018 Apr 27;81(4):1116-1120. doi: 10.1021/acs.jnatprod.8b00120. Epub 2018 Mar 5. [PubMed:29504746 ]
Yin Y, Chen H, Chen L, Bie X, Ding T, Zhang X, Wu B, Shen C, Zhang R: [Determination of three coriaria lactones in honey by ultra high performance liquid chromatography-high resolution mass spectrometry]. Se Pu. 2015 Jul;33(7):711-4. doi: 10.3724/sp.j.1123.2015.02057. [PubMed:26672199 ]
Larsen L, Joyce NI, Sansom CE, Cooney JM, Jensen DJ, Perry NB: Sweet Poisons: Honeys Contaminated with Glycosides of the Neurotoxin Tutin. J Nat Prod. 2015 Jun 26;78(6):1363-9. doi: 10.1021/acs.jnatprod.5b00241. Epub 2015 May 21. [PubMed:25993882 ]
Fields BA, Reeve J, Bartholomaeus A, Mueller U: Human pharmacokinetic study of tutin in honey; a plant-derived neurotoxin. Food Chem Toxicol. 2014 Oct;72:234-41. doi: 10.1016/j.fct.2014.07.032. Epub 2014 Jul 30. [PubMed:25084484 ]
Dor E, Aly R, Hershenhorn J: Pomegranate (Punica granatum) as Host of the Broomrapes Phelipanche aegyptiaca and Orobanche crenata in Israel. Plant Dis. 2014 Jun;98(6):859. doi: 10.1094/PDIS-10-13-1058-PDN. [PubMed:30708642 ]

Showing NP-Card for Tutin (NP0051972)

MOL for NP0051972 (Tutin)

3D MOL for NP0051972 (Tutin)

3D SDF for NP0051972 (Tutin)

3D-SDF for NP0051972 (Tutin)

PDB for NP0051972 (Tutin)

3D PDB for NP0051972 (Tutin)

SMILES for NP0051972 (Tutin)

INCHI for NP0051972 (Tutin)

Structure for NP0051972 (Tutin)

3D Structure for NP0051972 (Tutin)