NP-MRD: Showing NP-Card for (2'r,4's,7'r,9'r,10'r,11's)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-yl 3-hydroxy-3-methylbutanoate (NP0270706)

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Record Information

Version

2.0

Created at

2022-09-08 16:44:43 UTC

Updated at

2022-09-08 16:44:44 UTC

NP-MRD ID

NP0270706

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2'r,4's,7'r,9'r,10'r,11's)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-yl 3-hydroxy-3-methylbutanoate

Description

84474-35-1 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. (2'r,4's,7'r,9'r,10'r,11's)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-yl 3-hydroxy-3-methylbutanoate is found in Fusarium sporotrichioides. Based on a literature review very few articles have been published on 84474-35-1.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082218442D          

 34 37  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309082218442D          

 34 37  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0270706

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@]12C[C@H](OC(=O)CC(C)(C)O)C(C)=C[C@H]1O[C@@H]1[C@H](O)[C@@H](OC(C)=O)C2(C)C11CO1

> <INCHI_IDENTIFIER>
InChI=1S/C24H34O10/c1-12-7-16-23(10-30-13(2)25,8-15(12)33-17(27)9-21(4,5)29)22(6)19(32-14(3)26)18(28)20(34-16)24(22)11-31-24/h7,15-16,18-20,28-29H,8-11H2,1-6H3/t15-,16+,18+,19+,20+,22?,23+,24?/m0/s1

> <INCHI_KEY>
MLDQZNYFEGLVAS-IAQSYKHTSA-N

> <FORMULA>
C24H34O10

> <MOLECULAR_WEIGHT>
482.526

> <EXACT_MASS>
482.215197295

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
49.18522025890299

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2'R,4'S,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-4'-yl 3-hydroxy-3-methylbutanoate

> <JCHEM_LOGP>
-0.29576966799999993

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.133389286908105

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.06851545336254

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7421130974422567

> <JCHEM_POLAR_SURFACE_AREA>
141.12

> <JCHEM_REFRACTIVITY>
115.22529999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2'R,4'S,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-4'-yl 3-hydroxy-3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       7.321  -2.938   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.062  -2.052   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.665  -2.699   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.200  -0.518   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.941   0.369   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.080   1.903   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.269   0.924   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.711   1.465   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.900   0.487   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.342   1.028   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.595   2.547   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      11.531   0.049   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.973   0.590   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.415   1.131   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.433   2.032   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.514  -0.852   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.963   2.984   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.405   3.525   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.774   3.963   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.332   3.422   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.302   4.567   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.765   4.475   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.878   3.216   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.359   3.468   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.310   1.737   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.165   0.707   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.300   1.183   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.444   0.153   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.619   2.690   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.734   1.153   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.826  -0.384   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.834   2.693   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.770   1.580   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.338   3.058   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   20   30                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13                                                            
CONECT   17    8   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19    6   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   32                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   25    6   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   22   33   34                                             
CONECT   33   32   34                                                       
CONECT   34   33   32                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
3'-Hydroxy-T-2 toxin	MeSH

Chemical Formula

C₂₄H₃₄O₁₀

Average Mass

482.5260 Da

Monoisotopic Mass

482.21520 Da

IUPAC Name

(2'R,4'S,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-4'-yl 3-hydroxy-3-methylbutanoate

Traditional Name

(2'R,4'S,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-4'-yl 3-hydroxy-3-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@]12C[C@H](OC(=O)CC(C)(C)O)C(C)=C[C@H]1O[C@@H]1[C@H](O)[C@@H](OC(C)=O)C2(C)C11CO1

InChI Identifier

InChI=1S/C24H34O10/c1-12-7-16-23(10-30-13(2)25,8-15(12)33-17(27)9-21(4,5)29)22(6)19(32-14(3)26)18(28)20(34-16)24(22)11-31-24/h7,15-16,18-20,28-29H,8-11H2,1-6H3/t15-,16+,18+,19+,20+,22?,23+,24?/m0/s1

InChI Key

MLDQZNYFEGLVAS-IAQSYKHTSA-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 sporotrichioides	LOTUS Database	35616633

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
Tricarboxylic acid or derivatives
Oxepane
Fatty acid ester
Fatty acyl
Oxane
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	-0.3	ChemAxon
pKa (Strongest Acidic)	13.07	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	141.12 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	115.23 m³·mol⁻¹	ChemAxon
Polarizability	49.19 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00012669

Chemspider ID

96915

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

107753

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2'r,4's,7'r,9'r,10'r,11's)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-yl 3-hydroxy-3-methylbutanoate (NP0270706)

MOL for NP0270706 ((2'r,4's,7'r,9'r,10'r,11's)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-yl 3-hydroxy-3-methylbutanoate)

3D MOL for NP0270706 ((2'r,4's,7'r,9'r,10'r,11's)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-yl 3-hydroxy-3-methylbutanoate)

3D SDF for NP0270706 ((2'r,4's,7'r,9'r,10'r,11's)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-yl 3-hydroxy-3-methylbutanoate)

3D-SDF for NP0270706 ((2'r,4's,7'r,9'r,10'r,11's)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-yl 3-hydroxy-3-methylbutanoate)

PDB for NP0270706 ((2'r,4's,7'r,9'r,10'r,11's)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-yl 3-hydroxy-3-methylbutanoate)

3D PDB for NP0270706 ((2'r,4's,7'r,9'r,10'r,11's)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-yl 3-hydroxy-3-methylbutanoate)

SMILES for NP0270706 ((2'r,4's,7'r,9'r,10'r,11's)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-yl 3-hydroxy-3-methylbutanoate)

INCHI for NP0270706 ((2'r,4's,7'r,9'r,10'r,11's)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-yl 3-hydroxy-3-methylbutanoate)

Structure for NP0270706 ((2'r,4's,7'r,9'r,10'r,11's)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-yl 3-hydroxy-3-methylbutanoate)

3D Structure for NP0270706 ((2'r,4's,7'r,9'r,10'r,11's)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-yl 3-hydroxy-3-methylbutanoate)