NP-MRD: Showing NP-Card for 5,14,18,27-tetramethyl-2,7,11,17,25,30-hexaoxaspiro[hexacyclo[24.2.1.1¹⁶,¹⁹.0³,⁹.0⁶,⁸.0⁹,²⁷]triacontane-28,2'-oxirane]-4,13,20,22-tetraene-12,24-dione (NP0244886)

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Record Information

Version

2.0

Created at

2022-09-07 05:47:01 UTC

Updated at

2022-09-07 05:47:01 UTC

NP-MRD ID

NP0244886

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,14,18,27-tetramethyl-2,7,11,17,25,30-hexaoxaspiro[hexacyclo[24.2.1.1¹⁶,¹⁹.0³,⁹.0⁶,⁸.0⁹,²⁷]triacontane-28,2'-oxirane]-4,13,20,22-tetraene-12,24-dione

Description

5,14,18,27-Tetramethyl-2,7,11,17,25,30-hexaoxaspiro[hexacyclo[24.2.1.1¹⁶,¹⁹.0³,⁹.0⁶,⁸.0⁹,²⁷]Triacontane-28,2'-oxirane]-4,13,20,22-tetraene-12,24-dione belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain. Based on a literature review very few articles have been published on 5,14,18,27-tetramethyl-2,7,11,17,25,30-hexaoxaspiro[hexacyclo[24.2.1.1¹⁶,¹⁹.0³,⁹.0⁶,⁸.0⁹,²⁷]Triacontane-28,2'-oxirane]-4,13,20,22-tetraene-12,24-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072207472D          

 38 44  0  0  0  0            999 V2000
    7.7652    0.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309072207472D          

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    3.8092    3.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6119    3.3233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1192    3.8093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6644    3.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2957    3.8589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  4  0  0  0
  4  5  2  0  0  0  0
  4  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
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 15  1  0  0  0  0
  8 15  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 23 21  1  4  0  0  0
 23 24  2  0  0  0  0
 25 24  1  4  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  2 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 27 32  1  0  0  0  0
 32 33  1  0  0  0  0
 19 34  1  0  0  0  0
  8 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 17 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 36 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0244886

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC2CC(C)=CC(=O)OCC34C5OC5C(C)=CC3OC3CC(OC(=O)C=CC=CC1O2)C4(C)C31CO1

> <INCHI_IDENTIFIER>
InChI=1S/C29H34O9/c1-15-9-23(31)32-13-28-20(11-16(2)25-26(28)38-25)36-21-12-19(27(28,4)29(21)14-33-29)37-22(30)8-6-5-7-18-17(3)34-24(10-15)35-18/h5-9,11,17-21,24-26H,10,12-14H2,1-4H3

> <INCHI_KEY>
VXOJFQZXGUOVSR-UHFFFAOYSA-N

> <FORMULA>
C29H34O9

> <MOLECULAR_WEIGHT>
526.582

> <EXACT_MASS>
526.220282675

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
53.55074782836068

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,14,18,27-tetramethyl-2,7,11,17,25,30-hexaoxaspiro[hexacyclo[24.2.1.1^{16,19}.0^{3,9}.0^{6,8}.0^{9,27}]triacontane-28,2'-oxirane]-4,13,20,22-tetraene-12,24-dione

> <JCHEM_LOGP>
2.846130970999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.85845171217002

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5816232345227426

> <JCHEM_POLAR_SURFACE_AREA>
105.35000000000002

> <JCHEM_REFRACTIVITY>
135.26430000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5,14,18,27-tetramethyl-2,7,11,17,25,30-hexaoxaspiro[hexacyclo[24.2.1.1^{16,19}.0^{3,9}.0^{6,8}.0^{9,27}]triacontane-28,2'-oxirane]-4,13,20,22-tetraene-12,24-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      14.495   1.555   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.554   2.774   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.129   2.117   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.631   2.609   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       9.812   1.306   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       9.528   3.758   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.261   4.747   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.604   4.940   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.967   4.879   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.150   3.545   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.834   2.162   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.987   0.876   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.366   2.082   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.620   3.429   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.160   3.402   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.067   6.247   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.714   7.752   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.897   8.902   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.379   8.184   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.634   9.169   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.973  10.703   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.744  11.632   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.348  11.443   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.878  11.139   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.297  10.496   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.420   9.411   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.128   7.993   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      14.273   6.679   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      15.202   5.418   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.547   3.982   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      16.672   5.961   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      16.624   7.516   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      17.853   8.443   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.111   6.559   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.609   6.204   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.823   7.111   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.974   5.826   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       4.285   7.203   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   15   34                                             
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13   15                                                       
CONECT   15   14   13    8                                                  
CONECT   16    9   17                                                       
CONECT   17   16   18   36                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   34                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29    2                                                       
CONECT   31   29   32                                                       
CONECT   32   31   27   33                                                  
CONECT   33   32                                                            
CONECT   34   19    8   35   36                                             
CONECT   35   34                                                            
CONECT   36   34   17   37   38                                             
CONECT   37   36   38                                                       
CONECT   38   37   36                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₄O₉

Average Mass

526.5820 Da

Monoisotopic Mass

526.22028 Da

IUPAC Name

5,14,18,27-tetramethyl-2,7,11,17,25,30-hexaoxaspiro[hexacyclo[24.2.1.1^{16,19}.0^{3,9}.0^{6,8}.0^{9,27}]triacontane-28,2'-oxirane]-4,13,20,22-tetraene-12,24-dione

Traditional Name

5,14,18,27-tetramethyl-2,7,11,17,25,30-hexaoxaspiro[hexacyclo[24.2.1.1^{16,19}.0^{3,9}.0^{6,8}.0^{9,27}]triacontane-28,2'-oxirane]-4,13,20,22-tetraene-12,24-dione

CAS Registry Number

Not Available

SMILES

CC1OC2CC(C)=CC(=O)OCC34C5OC5C(C)=CC3OC3CC(OC(=O)C=CC=CC1O2)C4(C)C31CO1

InChI Identifier

InChI=1S/C29H34O9/c1-15-9-23(31)32-13-28-20(11-16(2)25-26(28)38-25)36-21-12-19(27(28,4)29(21)14-33-29)37-22(30)8-6-5-7-18-17(3)34-24(10-15)35-18/h5-9,11,17-21,24-26H,10,12-14H2,1-4H3

InChI Key

VXOJFQZXGUOVSR-UHFFFAOYSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Trichothecenes

Alternative Parents

Substituents

Trichothecene skeleton
Macrolide
Oxepane
Dicarboxylic acid or derivatives
Oxane
Meta-dioxolane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Acetal
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	2.85	ChemAxon
pKa (Strongest Acidic)	15.86	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	105.35 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	135.26 m³·mol⁻¹	ChemAxon
Polarizability	53.55 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163072653

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5,14,18,27-tetramethyl-2,7,11,17,25,30-hexaoxaspiro[hexacyclo[24.2.1.1¹⁶,¹⁹.0³,⁹.0⁶,⁸.0⁹,²⁷]triacontane-28,2'-oxirane]-4,13,20,22-tetraene-12,24-dione (NP0244886)

MOL for NP0244886 (5,14,18,27-tetramethyl-2,7,11,17,25,30-hexaoxaspiro[hexacyclo[24.2.1.1¹⁶,¹⁹.0³,⁹.0⁶,⁸.0⁹,²⁷]triacontane-28,2'-oxirane]-4,13,20,22-tetraene-12,24-dione)

3D MOL for NP0244886 (5,14,18,27-tetramethyl-2,7,11,17,25,30-hexaoxaspiro[hexacyclo[24.2.1.1¹⁶,¹⁹.0³,⁹.0⁶,⁸.0⁹,²⁷]triacontane-28,2'-oxirane]-4,13,20,22-tetraene-12,24-dione)

3D SDF for NP0244886 (5,14,18,27-tetramethyl-2,7,11,17,25,30-hexaoxaspiro[hexacyclo[24.2.1.1¹⁶,¹⁹.0³,⁹.0⁶,⁸.0⁹,²⁷]triacontane-28,2'-oxirane]-4,13,20,22-tetraene-12,24-dione)

3D-SDF for NP0244886 (5,14,18,27-tetramethyl-2,7,11,17,25,30-hexaoxaspiro[hexacyclo[24.2.1.1¹⁶,¹⁹.0³,⁹.0⁶,⁸.0⁹,²⁷]triacontane-28,2'-oxirane]-4,13,20,22-tetraene-12,24-dione)

PDB for NP0244886 (5,14,18,27-tetramethyl-2,7,11,17,25,30-hexaoxaspiro[hexacyclo[24.2.1.1¹⁶,¹⁹.0³,⁹.0⁶,⁸.0⁹,²⁷]triacontane-28,2'-oxirane]-4,13,20,22-tetraene-12,24-dione)

3D PDB for NP0244886 (5,14,18,27-tetramethyl-2,7,11,17,25,30-hexaoxaspiro[hexacyclo[24.2.1.1¹⁶,¹⁹.0³,⁹.0⁶,⁸.0⁹,²⁷]triacontane-28,2'-oxirane]-4,13,20,22-tetraene-12,24-dione)

SMILES for NP0244886 (5,14,18,27-tetramethyl-2,7,11,17,25,30-hexaoxaspiro[hexacyclo[24.2.1.1¹⁶,¹⁹.0³,⁹.0⁶,⁸.0⁹,²⁷]triacontane-28,2'-oxirane]-4,13,20,22-tetraene-12,24-dione)

INCHI for NP0244886 (5,14,18,27-tetramethyl-2,7,11,17,25,30-hexaoxaspiro[hexacyclo[24.2.1.1¹⁶,¹⁹.0³,⁹.0⁶,⁸.0⁹,²⁷]triacontane-28,2'-oxirane]-4,13,20,22-tetraene-12,24-dione)

Structure for NP0244886 (5,14,18,27-tetramethyl-2,7,11,17,25,30-hexaoxaspiro[hexacyclo[24.2.1.1¹⁶,¹⁹.0³,⁹.0⁶,⁸.0⁹,²⁷]triacontane-28,2'-oxirane]-4,13,20,22-tetraene-12,24-dione)

3D Structure for NP0244886 (5,14,18,27-tetramethyl-2,7,11,17,25,30-hexaoxaspiro[hexacyclo[24.2.1.1¹⁶,¹⁹.0³,⁹.0⁶,⁸.0⁹,²⁷]triacontane-28,2'-oxirane]-4,13,20,22-tetraene-12,24-dione)