NP-MRD: Showing NP-Card for Calonectrin (NP0337129)

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Record Information

Version

2.0

Created at

2024-09-11 09:26:08 UTC

Updated at

2024-09-11 09:26:09 UTC

NP-MRD ID

NP0337129

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Calonectrin

Description

Calonectrin was first documented in 2006 (PMID: 16604118). Based on a literature review a significant number of articles have been published on Calonectrin (PMID: 27120196) (PMID: 24434906) (PMID: 22095495) (PMID: 38928120) (PMID: 38673874).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262311582D          

 25 28  0  0  0  0            999 V2000
    4.3097   -1.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4787    2.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4790   -3.2531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0212    0.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3989   -0.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6257   -0.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9007   -1.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7989   -1.2953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7057    0.2288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2939    0.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5364   -1.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9501    1.6367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3081   -3.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1197   -1.6427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1275   -1.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396   -0.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1194   -0.5867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9900   -0.5456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4999   -0.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1372    1.7778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9156   -3.5643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2343    0.8623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2975    0.6825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4878   -2.2009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4934   -0.8715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
 11  1  1  0  0  0  0
 11  5  1  0  0  0  0
 11  7  2  0  0  0  0
 12  2  1  0  0  0  0
 13  3  1  0  0  0  0
 14  8  1  0  0  0  0
 15  7  1  0  0  0  0
 16 14  1  0  0  0  0
 17  4  1  0  0  0  0
 17  8  1  0  0  0  0
 18  6  1  0  0  0  0
 18  9  1  0  0  0  0
 18 15  1  0  0  0  0
 18 17  1  0  0  0  0
 19 10  1  0  0  0  0
 19 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20 12  2  0  0  0  0
 21 13  2  0  0  0  0
 22  9  1  0  0  0  0
 22 12  1  0  0  0  0
 23 10  1  0  0  0  0
 23 19  1  0  0  0  0
 24 13  1  0  0  0  0
 24 14  1  0  0  0  0
 25 15  1  0  0  0  0
 25 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0337129

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC12CCC(C)=CC1OC1C(CC2(C)C11CO1)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1/C19H26O6/c1-11-5-6-18(9-22-12(2)20)15(7-11)25-16-14(24-13(3)21)8-17(18,4)19(16)10-23-19/h7,14-16H,5-6,8-10H2,1-4H3

> <INCHI_KEY>
IGDIDZAQDRAJRB-UHFFFAOYNA-N

> <FORMULA>
C19H26O6

> <MOLECULAR_WEIGHT>
350.411

> <EXACT_MASS>
350.172938557

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.55907440742489

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
1.295995752333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.930401673270809

> <JCHEM_POLAR_SURFACE_AREA>
74.36000000000001

> <JCHEM_REFRACTIVITY>
87.89219999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
10'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2'-ylmethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0       8.045  -2.629   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.627   4.238   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.894  -6.072   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.906   0.556   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.345  -0.574   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.901  -0.037   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.415  -3.074   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.491  -2.418   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.184   0.427   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.549   0.200   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.601  -2.092   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.640   3.055   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.575  -5.611   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.223  -3.066   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.971  -2.537   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.194  -1.737   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.090  -1.095   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.715  -1.018   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.933  -0.219   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.123   3.319   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.709  -6.653   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.171   1.610   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.555   1.274   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.911  -4.108   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       2.788  -1.627   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4   17                                                            
CONECT    5    6   11                                                       
CONECT    6    5   18                                                       
CONECT    7   11   15                                                       
CONECT    8   14   17                                                       
CONECT    9   18   22                                                       
CONECT   10   19   23                                                       
CONECT   11    1    5    7                                                  
CONECT   12    2   20   22                                                  
CONECT   13    3   21   24                                                  
CONECT   14    8   16   24                                                  
CONECT   15    7   18   25                                                  
CONECT   16   14   19   25                                                  
CONECT   17    4    8   18   19                                             
CONECT   18    6    9   15   17                                             
CONECT   19   10   16   17   23                                             
CONECT   20   12                                                            
CONECT   21   13                                                            
CONECT   22    9   12                                                       
CONECT   23   10   19                                                       
CONECT   24   13   14                                                       
CONECT   25   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₆O₆

Average Mass

350.4110 Da

Monoisotopic Mass

350.17294 Da

IUPAC Name

[10'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2'-yl]methyl acetate

Traditional Name

10'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-2'-ylmethyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC12CCC(C)=CC1OC1C(CC2(C)C11CO1)OC(C)=O

InChI Identifier

InChI=1/C19H26O6/c1-11-5-6-18(9-22-12(2)20)15(7-11)25-16-14(24-13(3)21)8-17(18,4)19(16)10-23-19/h7,14-16H,5-6,8-10H2,1-4H3

InChI Key

IGDIDZAQDRAJRB-UHFFFAOYNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Classification

Not classified

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	1.3	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	74.36 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	87.89 m³·mol⁻¹	ChemAxon
Polarizability	36.56 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

McCormick SP, Alexander NJ, Proctor RH: Heterologous expression of two trichothecene P450 genes in Fusarium verticillioides. Can J Microbiol. 2006 Mar;52(3):220-6. doi: 10.1139/w05-124. [PubMed:16604118 ]
Maeda K, Tanaka A, Sugiura R, Koshino H, Tokai T, Sato M, Nakajima Y, Tanahashi Y, Kanamaru K, Kobayashi T, Nishiuchi T, Fujimura M, Takahashi-Ando N, Kimura M: Hydroxylations of trichothecene rings in the biosynthesis of Fusarium trichothecenes: evolution of alternative pathways in the nivalenol chemotype. Environ Microbiol. 2016 Nov;18(11):3798-3811. doi: 10.1111/1462-2920.13338. Epub 2016 Jun 27. [PubMed:27120196 ]
Fruhmann P, Hametner C, Mikula H, Adam G, Krska R, Frohlich J: Stereoselective Luche reduction of deoxynivalenol and three of its acetylated derivatives at C8. Toxins (Basel). 2014 Jan 10;6(1):325-36. doi: 10.3390/toxins6010325. [PubMed:24434906 ]
Kadota T, Kimura M, Hirano S, Tajima O, Nakajima T, Kamata Y, Sugita-Konishi Y: Development of a simultaneous liquid chromatography/tandem mass spectrometric method for the determination of type B trichothecenes, their derivatives, and precursors in wheat. Rapid Commun Mass Spectrom. 2011 Dec 15;25(23):3481-90. doi: 10.1002/rcm.5250. [PubMed:22095495 ]
Kasahara E, Kitamura Y, Katada M, Mizuki M, Okumura N, Sano T, Koizumi Y, Maeda K, Takahashi-Ando N, Kimura M, Nakajima Y: Attempting to Create a Pathway to 15-Deacetylcalonectrin with Limited Accumulation in Cultures of Fusarium Tri3 Mutants: Insight into Trichothecene Biosynthesis Machinery. Int J Mol Sci. 2024 Jun 11;25(12):6414. doi: 10.3390/ijms25126414. [PubMed:38928120 ]
Koizumi Y, Nakajima Y, Tanaka Y, Matsui K, Sakabe M, Maeda K, Sato M, Koshino H, Sato S, Kimura M, Takahashi-Ando N: A Role in 15-Deacetylcalonectrin Acetylation in the Non-Enzymatic Cyclization of an Earlier Bicyclic Intermediate in Fusarium Trichothecene Biosynthesis. Int J Mol Sci. 2024 Apr 12;25(8):4288. doi: 10.3390/ijms25084288. [PubMed:38673874 ]

Showing NP-Card for Calonectrin (NP0337129)

MOL for NP0337129 (Calonectrin)

3D MOL for NP0337129 (Calonectrin)

3D SDF for NP0337129 (Calonectrin)

3D-SDF for NP0337129 (Calonectrin)

PDB for NP0337129 (Calonectrin)

3D PDB for NP0337129 (Calonectrin)

SMILES for NP0337129 (Calonectrin)

INCHI for NP0337129 (Calonectrin)

Structure for NP0337129 (Calonectrin)

3D Structure for NP0337129 (Calonectrin)