NP-MRD: Showing NP-Card for Isotrichodermin (NP0059149)

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Record Information

Version

2.0

Created at

2022-04-28 04:25:24 UTC

Updated at

2022-04-28 04:25:24 UTC

NP-MRD ID

NP0059149

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isotrichodermin

Description

(1'S,2S,2'R,7'R,9'R,10'R)-1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]Dodecan]-5'-en-10'-yl acetate 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. Isotrichodermin is found in Fusarium culmorum and Fusarium roseum. Based on a literature review very few articles have been published on (1'S,2S,2'R,7'R,9'R,10'R)-1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]Dodecan]-5'-en-10'-yl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282206252D          

 21 24  0  0  1  0            999 V2000
    3.3584    0.4952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7212    1.0193    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8566    1.8331    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6290    2.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2661    1.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1308    0.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0386    1.8885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3047    2.4463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4811    2.3972    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5184    1.4425    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0006    0.6177    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2373    0.9307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0061    1.7227    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1923    1.8580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0974    2.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9113    2.7658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4267    3.2676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0498   -0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9482    0.8463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7170    1.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6471    0.1976    0.0000 C   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  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  3  8  1  6  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 11 18  1  1  0  0  0
 10 19  1  1  0  0  0
 19 20  1  0  0  0  0
 10 20  1  0  0  0  0
  2 21  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0059149

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1C[C@]2(C)[C@]3(CO3)[C@@H]1O[C@@H]1C=C(C)CC[C@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O4/c1-10-5-6-15(3)13(7-10)21-14-12(20-11(2)18)8-16(15,4)17(14)9-19-17/h7,12-14H,5-6,8-9H2,1-4H3/t12-,13-,14-,15+,16+,17+/m1/s1

> <INCHI_KEY>
OZXJPPYWZVBMGW-FFRIZKCHSA-N

> <FORMULA>
C17H24O4

> <MOLECULAR_WEIGHT>
292.375

> <EXACT_MASS>
292.167459253

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
0.0

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,2S,2'R,7'R,9'R,10'R)-1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-10'-yl acetate

> <ALOGPS_LOGP>
2.16

> <JCHEM_LOGP>
2.1356414986666645

> <ALOGPS_LOGS>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9304289390245315

> <JCHEM_POLAR_SURFACE_AREA>
48.06

> <JCHEM_REFRACTIVITY>
76.966

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.19e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2S,2'R,7'R,9'R,10'R)-1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-10'-yl acetate

> <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       6.269   0.924   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.080   1.903   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.332   3.422   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.774   3.963   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.963   2.984   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.711   1.465   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.405   3.525   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.302   4.567   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.765   4.475   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.834   2.693   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.734   1.153   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.310   1.737   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.878   3.216   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.359   3.468   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.182   4.910   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.701   5.163   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.796   6.099   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.826  -0.384   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.770   1.580   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.338   3.058   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.941   0.369   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   11   21                                             
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5                                                            
CONECT    8    3    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11   19   20                                             
CONECT   11   10    2   12   18                                             
CONECT   12   11   13                                                       
CONECT   13   12    9   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   11                                                            
CONECT   19   10   20                                                       
CONECT   20   19   10                                                       
CONECT   21    2                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Value	Source
(1's,2S,2'r,7'r,9'r,10'r)-1',2',5'-Trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0,]dodecan]-5'-en-10'-yl acetic acid	Generator

Chemical Formula

C₁₇H₂₄O₄

Average Mass

292.3750 Da

Monoisotopic Mass

292.16746 Da

IUPAC Name

(1'S,2S,2'R,7'R,9'R,10'R)-1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-10'-yl acetate

Traditional Name

(1'S,2S,2'R,7'R,9'R,10'R)-1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-10'-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C[C@]2(C)[C@]3(CO3)[C@@H]1O[C@@H]1C=C(C)CC[C@]21C

InChI Identifier

InChI=1S/C17H24O4/c1-10-5-6-15(3)13(7-10)21-14-12(20-11(2)18)8-16(15,4)17(14)9-19-17/h7,12-14H,5-6,8-9H2,1-4H3/t12-,13-,14-,15+,16+,17+/m1/s1

InChI Key

OZXJPPYWZVBMGW-FFRIZKCHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Fusarium culmorum	Fungi	KNApSAcK
Fusarium sambucinum	Fungi	KNApSAcK

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
Oxepane
Oxane
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	2.16	ALOGPS
logP	2.14	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	48.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	76.97 m³·mol⁻¹	ChemAxon
Polarizability	0 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	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

14733838

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Isotrichodermin (NP0059149)

MOL for NP0059149 (Isotrichodermin)

3D MOL for NP0059149 (Isotrichodermin)

3D SDF for NP0059149 (Isotrichodermin)

3D-SDF for NP0059149 (Isotrichodermin)

PDB for NP0059149 (Isotrichodermin)

3D PDB for NP0059149 (Isotrichodermin)

SMILES for NP0059149 (Isotrichodermin)

INCHI for NP0059149 (Isotrichodermin)

Structure for NP0059149 (Isotrichodermin)

3D Structure for NP0059149 (Isotrichodermin)