NP-MRD: Showing NP-Card for (1s,2s,5r,7r,8r,9s,11r)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecane-5,8,11-triol (NP0206777)

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Record Information

Version

2.0

Created at

2022-09-05 03:09:08 UTC

Updated at

2022-09-05 03:09:09 UTC

NP-MRD ID

NP0206777

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,5r,7r,8r,9s,11r)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecane-5,8,11-triol

Description

5-Hydroxyculmorin belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. (1s,2s,5r,7r,8r,9s,11r)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecane-5,8,11-triol is found in Fusarium culmorum and Fusarium graminearum. (1s,2s,5r,7r,8r,9s,11r)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecane-5,8,11-triol was first documented in 2014 (PMID: 24844356). Based on a literature review a small amount of articles have been published on 5-Hydroxyculmorin (PMID: 32316403) (PMID: 27690101).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 46  0  0  0  0  0  0  0  0999 V2000
    1.9967    0.2444    2.0242 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5351    0.2860    0.5837 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6442    1.3504    0.1770 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9385   -0.8732   -0.2733 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0093   -0.5182   -1.1750 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1594   -1.8642   -0.9443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3634   -1.8314   -1.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7506   -0.8113   -0.2862 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4484   -1.4778    0.9748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0890    0.3283   -0.9678 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1391    1.0949   -1.7404 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9077    2.4449   -1.7968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4099    0.6904   -1.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8596   -0.0103    0.1407 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9221   -0.5804    0.9752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9744    1.0008    0.9453 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6757    2.2202    0.7104 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3397    1.0619    0.3013 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7956    1.2811    2.4271 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5595   -0.4400    2.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1105    0.0627    2.1156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4853    2.2560    0.7641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4426    1.5259   -0.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6305    0.8680    0.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6150   -1.4468    0.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2726   -1.3315   -1.6307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3321   -2.9216   -0.5501 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5364   -2.0313   -2.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6233   -1.6275   -2.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8401   -2.8140   -0.9823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2960   -2.2647    1.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6100   -1.0125    1.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4075   -2.1443    1.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7281    0.1845   -1.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1562    0.6805   -2.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7080    2.9030   -2.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9250    1.6108   -0.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0331    0.0172   -1.6546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8572    0.0399    0.8403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6807   -0.4520    2.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2123   -1.6100    0.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0586    0.9099    2.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4758    2.8800    1.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4776    2.1213   -0.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  1
 14 13  1  0
 13 11  1  0
 11 12  1  0
 11 10  1  0
 10 18  1  0
 18 16  1  0
 16 17  1  0
 18  2  1  0
  2  1  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
 16 14  1  0
  8 14  1  0
  8 10  1  0
 15 39  1  0
 15 40  1  0
 15 41  1  0
 13 37  1  0
 13 38  1  0
 11 35  1  6
 12 36  1  0
 10 34  1  6
 18 44  1  6
 16 42  1  1
 17 43  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  1
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
M  END

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       4.112  -2.584   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.759  -1.849   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.309  -3.322   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.799  -0.610   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.298  -0.962   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.416   0.978   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.948   1.695   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.395   0.920   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.845   1.832   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.096  -0.929   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.754  -1.296   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.294  -1.278   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.678  -0.202   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.547   0.710   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.748   2.237   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.224  -0.076   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.712   0.322   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.941  -1.675   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   18                                             
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   14                                             
CONECT    9    8                                                            
CONECT   10    8   11   18                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    8   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   10    2                                                  
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₆O₃

Average Mass

254.3700 Da

Monoisotopic Mass

254.18819 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@]12C[C@@H](O)[C@H]3[C@@H]([C@H]1O)C(C)(C)[C@H](O)CC[C@]23C

InChI Identifier

InChI=1S/C15H26O3/c1-13(2)9(17)5-6-14(3)10-8(16)7-15(14,4)12(18)11(10)13/h8-12,16-18H,5-7H2,1-4H3/t8-,9-,10+,11+,12-,14+,15-/m1/s1

InChI Key

XFKGEQRMYJCXFK-OFTJPINFSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Fusarium culmorum	LOTUS Database	35616633
Fusarium graminearum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Bornane monoterpenoid
Cyclic alcohol
Secondary alcohol
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78442610

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139585563

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Spanic V, Katanic Z, Sulyok M, Krska R, Puskas K, Vida G, Drezner G, Sarkanj B: Multiple Fungal Metabolites Including Mycotoxins in Naturally Infected and Fusarium-Inoculated Wheat Samples. Microorganisms. 2020 Apr 17;8(4):578. doi: 10.3390/microorganisms8040578. [PubMed:32316403 ]
Humer E, Lucke A, Harder H, Metzler-Zebeli BU, Bohm J, Zebeli Q: Effects of Citric and Lactic Acid on the Reduction of Deoxynivalenol and Its Derivatives in Feeds. Toxins (Basel). 2016 Sep 28;8(10):285. doi: 10.3390/toxins8100285. [PubMed:27690101 ]
Delgado RM, Sulyok M, Jirsa O, Spitzer T, Krska R, Polisenska I: Relationship between lutein and mycotoxin content in durum wheat. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2014;31(7):1274-83. doi: 10.1080/19440049.2014.925589. Epub 2014 Jun 9. [PubMed:24844356 ]
LOTUS database [Link]

Showing NP-Card for (1s,2s,5r,7r,8r,9s,11r)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecane-5,8,11-triol (NP0206777)

MOL for NP0206777 ((1s,2s,5r,7r,8r,9s,11r)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecane-5,8,11-triol)

3D MOL for NP0206777 ((1s,2s,5r,7r,8r,9s,11r)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecane-5,8,11-triol)

3D SDF for NP0206777 ((1s,2s,5r,7r,8r,9s,11r)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecane-5,8,11-triol)

3D-SDF for NP0206777 ((1s,2s,5r,7r,8r,9s,11r)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecane-5,8,11-triol)

PDB for NP0206777 ((1s,2s,5r,7r,8r,9s,11r)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecane-5,8,11-triol)

3D PDB for NP0206777 ((1s,2s,5r,7r,8r,9s,11r)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecane-5,8,11-triol)

SMILES for NP0206777 ((1s,2s,5r,7r,8r,9s,11r)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecane-5,8,11-triol)

INCHI for NP0206777 ((1s,2s,5r,7r,8r,9s,11r)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecane-5,8,11-triol)

Structure for NP0206777 ((1s,2s,5r,7r,8r,9s,11r)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecane-5,8,11-triol)

3D Structure for NP0206777 ((1s,2s,5r,7r,8r,9s,11r)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecane-5,8,11-triol)