NP-MRD: Showing NP-Card for (1's,2r,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 pentanoate (NP0152371)

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Record Information

Version

2.0

Created at

2022-09-02 08:50:13 UTC

Updated at

2022-09-02 08:50:13 UTC

NP-MRD ID

NP0152371

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1's,2r,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 pentanoate

Description

8-N-Pentanoylneosolaniol 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. (1's,2r,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 pentanoate is found in Fusarium sporotrichioides. (1's,2r,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 pentanoate was first documented in 1991 (PMID: 1800633). Based on a literature review very few articles have been published on 8-n-Pentanoylneosolaniol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022210502D          

 33 36  0  0  1  0            999 V2000
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   -3.4408   -3.6530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0118   -3.6530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2974   -4.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6392   -4.3473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  8 18  1  0  0  0  0
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 32 33  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309022210502D          

 33 36  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0152371

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC(=O)O[C@H]1C[C@@]2(COC(C)=O)[C@H](O[C@@H]3[C@H](O)[C@@H](OC(C)=O)[C@@]2(C)[C@@]32CO2)C=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C24H34O9/c1-6-7-8-18(27)32-16-10-23(11-29-14(3)25)17(9-13(16)2)33-21-19(28)20(31-15(4)26)22(23,5)24(21)12-30-24/h9,16-17,19-21,28H,6-8,10-12H2,1-5H3/t16-,17+,19+,20+,21+,22+,23+,24+/m0/s1

> <INCHI_KEY>
QXHICULSTMOREA-FHAHJZMBSA-N

> <FORMULA>
C24H34O9

> <MOLECULAR_WEIGHT>
466.527

> <EXACT_MASS>
466.220282675

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
47.92811203658118

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,2R,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 pentanoate

> <ALOGPS_LOGP>
2.12

> <JCHEM_LOGP>
1.1769871256666655

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.072305054496205

> <JCHEM_PKA_STRONGEST_BASIC>
-3.64197376916336

> <JCHEM_POLAR_SURFACE_AREA>
120.89000000000001

> <JCHEM_REFRACTIVITY>
113.5956

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.29e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2R,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 pentanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -7.756  -7.589   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.423  -6.819   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.089  -7.589   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.755  -6.819   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.422  -7.589   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.422  -9.129   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.088  -6.819   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.246  -7.589   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.579  -6.819   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.913  -7.589   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.798  -6.053   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.410  -5.385   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.295  -3.849   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.568  -2.982   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.092  -3.181   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.913  -9.129   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.579  -9.899   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.246  -9.129   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.088  -9.899   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.117 -10.089   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.618  -9.746   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.287  -8.359   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.827  -8.359   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.618  -6.971   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.579  -5.767   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.101  -5.997   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.062  -4.793   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.664  -7.430   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.117  -6.629   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.774  -5.127   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.257  -8.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.125  -6.727   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.793  -8.115   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   18                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   16   29                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   10   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17    8   19                                                  
CONECT   19   18                                                            
CONECT   20   16   21                                                       
CONECT   21   20   22   31                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   24   10   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   21   32   33                                             
CONECT   32   31   33                                                       
CONECT   33   32   31                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
8-Pentanoylneosolaniol	MeSH

Chemical Formula

C₂₄H₃₄O₉

Average Mass

466.5270 Da

Monoisotopic Mass

466.22028 Da

IUPAC Name

(1'S,2R,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 pentanoate

Traditional Name

(1'S,2R,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 pentanoate

CAS Registry Number

Not Available

SMILES

CCCCC(=O)O[C@H]1C[C@@]2(COC(C)=O)[C@H](O[C@@H]3[C@H](O)[C@@H](OC(C)=O)[C@@]2(C)[C@@]32CO2)C=C1C

InChI Identifier

InChI=1S/C24H34O9/c1-6-7-8-18(27)32-16-10-23(11-29-14(3)25)17(9-13(16)2)33-21-19(28)20(31-15(4)26)22(23,5)24(21)12-30-24/h9,16-17,19-21,28H,6-8,10-12H2,1-5H3/t16-,17+,19+,20+,21+,22+,23+,24+/m0/s1

InChI Key

QXHICULSTMOREA-FHAHJZMBSA-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
Fatty acid ester
Oxepane
Oxane
Fatty acyl
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Alcohol
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	2.12	ALOGPS
logP	1.18	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	13.07	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	120.89 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	113.6 m³·mol⁻¹	ChemAxon
Polarizability	47.93 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

Not Available

Chemspider ID

24718637

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44576029

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bekele E, Rottinghaus AA, Rottinghaus GE, Casper HH, Fort DM, Barnes CL, Tempesta MS: Two new trichothecenes from Fusarium sporotrichioides. J Nat Prod. 1991 Sep-Oct;54(5):1303-8. doi: 10.1021/np50077a011. [PubMed:1800633 ]
LOTUS database [Link]

Showing NP-Card for (1's,2r,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 pentanoate (NP0152371)

MOL for NP0152371 ((1's,2r,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 pentanoate)

3D MOL for NP0152371 ((1's,2r,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 pentanoate)

3D SDF for NP0152371 ((1's,2r,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 pentanoate)

3D-SDF for NP0152371 ((1's,2r,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 pentanoate)

PDB for NP0152371 ((1's,2r,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 pentanoate)

3D PDB for NP0152371 ((1's,2r,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 pentanoate)

SMILES for NP0152371 ((1's,2r,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 pentanoate)

INCHI for NP0152371 ((1's,2r,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 pentanoate)

Structure for NP0152371 ((1's,2r,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 pentanoate)

3D Structure for NP0152371 ((1's,2r,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 pentanoate)