NP-MRD: Showing NP-Card for Pyrethrosine (NP0050230)

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Record Information

Version

1.0

Created at

2022-04-27 20:49:04 UTC

Updated at

2022-04-27 20:49:04 UTC

NP-MRD ID

NP0050230

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pyrethrosine

Description

(1S,3S,5R,8E,10R,12R,13S,16S)-12-methoxy-3,8-dimethyl-4,11,15-trioxatetracyclo[8.5.1.0³,⁵.0¹³,¹⁶]Hexadec-8-en-14-one belongs to the class of organic compounds known as furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyrethrosine is found in Chrysanthemum cinerariifolium . Based on a literature review very few articles have been published on (1S,3S,5R,8E,10R,12R,13S,16S)-12-methoxy-3,8-dimethyl-4,11,15-trioxatetracyclo[8.5.1.0³,⁵.0¹³,¹⁶]Hexadec-8-en-14-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272222492D          

 21 24  0  0  1  0            999 V2000
    2.6570   -0.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8687   -0.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2638   -0.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4755   -0.6599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1294   -0.0989    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0541    0.7055    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8424    0.9488    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4472    0.3877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2355    0.6310    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8404    0.0700    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0238    0.8744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9922    1.4193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7782    1.8611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0409    1.9594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4428    2.6799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3876    1.2108    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1081    0.8089    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9485   -0.0005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8567    1.1555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5312    0.6805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8850    0.1263    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  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  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
  1 10  1  0  0  0  0
 10 11  1  6  0  0  0
  9 11  1  0  0  0  0
  9 12  1  1  0  0  0
  7 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 16 14  1  1  0  0  0
  6 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 18  1  1  0  0  0
 17 19  1  1  0  0  0
 19 20  1  0  0  0  0
  3 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050230

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1O[C@@H]2\C=C(C)\CC[C@H]3O[C@@]3(C)C[C@@H]3OC(=O)[C@H]1[C@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C16H22O5/c1-8-4-5-11-16(2,21-11)7-10-12-9(6-8)20-15(18-3)13(12)14(17)19-10/h6,9-13,15H,4-5,7H2,1-3H3/b8-6+/t9-,10+,11-,12-,13-,15-,16+/m1/s1

> <INCHI_KEY>
TUUBFKVUAKIOMJ-AUKVQBDGSA-N

> <FORMULA>
C16H22O5

> <MOLECULAR_WEIGHT>
294.347

> <EXACT_MASS>
294.146723808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
30.27387542318681

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3S,5R,8E,10R,12R,13S,16S)-12-methoxy-3,8-dimethyl-4,11,15-trioxatetracyclo[8.5.1.0^{3,5}.0^{13,16}]hexadec-8-en-14-one

> <ALOGPS_LOGP>
1.43

> <JCHEM_LOGP>
1.515609605666666

> <ALOGPS_LOGS>
-2.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.007304642638797

> <JCHEM_PKA_STRONGEST_BASIC>
-3.818855152939642

> <JCHEM_POLAR_SURFACE_AREA>
57.290000000000006

> <JCHEM_REFRACTIVITY>
74.47630000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.28e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,5R,8E,10R,12R,13S,16S)-12-methoxy-3,8-dimethyl-4,11,15-trioxatetracyclo[8.5.1.0^{3,5}.0^{13,16}]hexadec-8-en-14-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0       4.960  -1.371   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.488  -1.825   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.359  -0.778   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.888  -1.232   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.242  -0.185   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.101   1.317   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.572   1.771   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.702   0.724   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.173   1.178   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.302   0.131   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.645   1.632   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.719   2.649   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.453   3.474   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.076   3.658   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.827   5.002   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.723   2.260   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.068   1.510   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.771  -0.001   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -3.466   2.157   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.725   1.270   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.519   0.236   0.000  0.00  0.00           C+0
CONECT    1    2   10                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7   16                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11   12                                             
CONECT   10    9    1   11                                                  
CONECT   11   10    9                                                       
CONECT   12    9                                                            
CONECT   13    7   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    6   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17    5                                                       
CONECT   19   17   20                                                       
CONECT   20   19                                                            
CONECT   21    3                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₂O₅

Average Mass

294.3470 Da

Monoisotopic Mass

294.14672 Da

IUPAC Name

(1S,3S,5R,8E,10R,12R,13S,16S)-12-methoxy-3,8-dimethyl-4,11,15-trioxatetracyclo[8.5.1.0^{3,5}.0^{13,16}]hexadec-8-en-14-one

Traditional Name

(1S,3S,5R,8E,10R,12R,13S,16S)-12-methoxy-3,8-dimethyl-4,11,15-trioxatetracyclo[8.5.1.0^{3,5}.0^{13,16}]hexadec-8-en-14-one

CAS Registry Number

Not Available

SMILES

CO[C@@H]1O[C@@H]2\C=C(C)\CC[C@H]3O[C@@]3(C)C[C@@H]3OC(=O)[C@H]1[C@H]23

InChI Identifier

InChI=1S/C16H22O5/c1-8-4-5-11-16(2,21-11)7-10-12-9(6-8)20-15(18-3)13(12)14(17)19-10/h6,9-13,15H,4-5,7H2,1-3H3/b8-6+/t9-,10+,11-,12-,13-,15-,16+/m1/s1

InChI Key

TUUBFKVUAKIOMJ-AUKVQBDGSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Chrysanthemum cinerariifolium	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furofurans

Sub Class

Not Available

Direct Parent

Furofurans

Alternative Parents

Substituents

Furofuran
Gamma butyrolactone
Tetrahydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Acetal
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	1.43	ALOGPS
logP	1.52	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	19.01	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.29 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.48 m³·mol⁻¹	ChemAxon
Polarizability	30.27 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

163106083

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Pyrethrosine (NP0050230)

MOL for NP0050230 (Pyrethrosine)

3D MOL for NP0050230 (Pyrethrosine)

3D SDF for NP0050230 (Pyrethrosine)

3D-SDF for NP0050230 (Pyrethrosine)

PDB for NP0050230 (Pyrethrosine)

3D PDB for NP0050230 (Pyrethrosine)

SMILES for NP0050230 (Pyrethrosine)

INCHI for NP0050230 (Pyrethrosine)

Structure for NP0050230 (Pyrethrosine)

3D Structure for NP0050230 (Pyrethrosine)