NP-MRD: Showing NP-Card for Fenugrin A (NP0047115)

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Record Information

Version

2.0

Created at

2022-03-17 20:34:53 UTC

Updated at

2022-03-17 20:34:53 UTC

NP-MRD ID

NP0047115

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Fenugrin A

Description

Phenothrin, also known as sumithrin or hegor antipoux, belongs to the class of organic compounds known as pyrethroids. These are organic compounds similar to the pyrethrins. Some pyrethroids containing a chrysanthemic acid esterified with a cyclopentenone (pyrethrins), or with a phenoxybenzyl group. Phenothrin is an extremely weak basic (essentially neutral) compound (based on its pKa). Phenothrin is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652307282022242D          

 26 28  0  0  0  0            999 V2000
    0.3020   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2259   -1.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4899   -1.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2717   -6.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9862   -5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572   -5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9862   -4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572   -4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2717   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2717   -3.6020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  9  8  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 12  8  1  0  0  0  0
 16  1  1  0  0  0  0
 16  2  1  0  0  0  0
 16 13  2  0  0  0  0
 17  9  1  0  0  0  0
 17 14  2  0  0  0  0
 17 15  1  0  0  0  0
 18 10  2  0  0  0  0
 18 11  1  0  0  0  0
 19 12  2  0  0  0  0
 19 14  1  0  0  0  0
 20 13  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23  3  1  0  0  0  0
 23  4  1  0  0  0  0
 23 20  1  0  0  0  0
 23 21  1  0  0  0  0
 24 22  2  0  0  0  0
 25 15  1  0  0  0  0
 25 22  1  0  0  0  0
 26 18  1  0  0  0  0
 26 19  1  0  0  0  0
M  END


  Mrv1652307282022242D          

 26 28  0  0  0  0            999 V2000
    0.3020   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2259   -1.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4899   -1.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2717   -6.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9862   -5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572   -5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9862   -4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572   -4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2717   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2717   -3.6020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  9  8  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 12  8  1  0  0  0  0
 16  1  1  0  0  0  0
 16  2  1  0  0  0  0
 16 13  2  0  0  0  0
 17  9  1  0  0  0  0
 17 14  2  0  0  0  0
 17 15  1  0  0  0  0
 18 10  2  0  0  0  0
 18 11  1  0  0  0  0
 19 12  2  0  0  0  0
 19 14  1  0  0  0  0
 20 13  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23  3  1  0  0  0  0
 23  4  1  0  0  0  0
 23 20  1  0  0  0  0
 23 21  1  0  0  0  0
 24 22  2  0  0  0  0
 25 15  1  0  0  0  0
 25 22  1  0  0  0  0
 26 18  1  0  0  0  0
 26 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047115

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CC1C(C(=O)OCC2=CC(OC3=CC=CC=C3)=CC=C2)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C23H26O3/c1-16(2)13-20-21(23(20,3)4)22(24)25-15-17-9-8-12-19(14-17)26-18-10-6-5-7-11-18/h5-14,20-21H,15H2,1-4H3

> <INCHI_KEY>
SBNFWQZLDJGRLK-UHFFFAOYSA-N

> <FORMULA>
C23H26O3

> <MOLECULAR_WEIGHT>
350.4507

> <EXACT_MASS>
350.188194698

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
39.2035850674092

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3-phenoxyphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate

> <ALOGPS_LOGP>
6.42

> <JCHEM_LOGP>
5.571767122333333

> <ALOGPS_LOGS>
-5.24

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.69143746770052

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
103.83829999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.01e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenothrin

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-JUL-20         0                                  
HETATM    1  C   UNK     0       0.564  -6.724   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.897  -4.414   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.155  -3.630   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.514  -3.630   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.441 -11.344   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.774 -10.574   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.107 -10.574   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.773  -3.644   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.439  -4.414   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.774  -9.034   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.107  -9.034   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.107  -4.414   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.231  -6.724   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.773  -6.724   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.106  -6.724   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.897  -5.954   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.439  -5.954   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.441  -8.264   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.107  -5.954   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.565  -5.954   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.105  -5.954   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.438  -6.724   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.438  -8.264   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       8.772  -5.954   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      15.441  -6.724   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   16                                                            
CONECT    3   23                                                            
CONECT    4   23                                                            
CONECT    5    6    7                                                       
CONECT    6    5   10                                                       
CONECT    7    5   11                                                       
CONECT    8    9   12                                                       
CONECT    9    8   17                                                       
CONECT   10    6   18                                                       
CONECT   11    7   18                                                       
CONECT   12    8   19                                                       
CONECT   13   16   20                                                       
CONECT   14   17   19                                                       
CONECT   15   17   25                                                       
CONECT   16    1    2   13                                                  
CONECT   17    9   14   15                                                  
CONECT   18   10   11   26                                                  
CONECT   19   12   14   26                                                  
CONECT   20   13   21   23                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21   24   25                                                  
CONECT   23    3    4   20   21                                             
CONECT   24   22                                                            
CONECT   25   15   22                                                       
CONECT   26   18   19                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid (3-phenoxyphenyl)methyl ester	ChEBI
Sumithrin	ChEBI
Hegor antipoux	Kegg
2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate (3-phenoxyphenyl)methyl ester	Generator
(3-Phenoxyphenyl)methyl cis,trans-(+)-2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate	MeSH
Phenothrin, (cis-(+-))-isomer	MeSH
Phenothrin, (1S-cis)-isomer	MeSH
D-Phenothrin	MeSH
Phenothrin, (1S-trans)-isomer	MeSH
Phenothrin, (1R-trans)-isomer	MeSH
Phenothrin, (1R-cis)-isomer	MeSH
Phenothrin, (trans-(+-))-isomer	MeSH

Chemical Formula

C₂₃H₂₆O₃

Average Mass

350.4507 Da

Monoisotopic Mass

350.18819 Da

IUPAC Name

(3-phenoxyphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate

Traditional Name

phenothrin

CAS Registry Number

26002-80-2

SMILES

CC(C)=CC1C(C(=O)OCC2=CC(OC3=CC=CC=C3)=CC=C2)C1(C)C

InChI Identifier

InChI=1S/C23H26O3/c1-16(2)13-20-21(23(20,3)4)22(24)25-15-17-9-8-12-19(14-17)26-18-10-6-5-7-11-18/h5-14,20-21H,15H2,1-4H3

InChI Key

SBNFWQZLDJGRLK-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Trigonella foenum-graecum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrethroids. These are organic compounds similar to the pyrethrins. Some pyrethroids containing a chrysanthemic acid esterified with a cyclopentenone (pyrethrins), or with a phenoxybenzyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Pyrethroids

Alternative Parents

Substituents

Pyrethroid skeleton
Diphenylether
Diaryl ether
Aromatic monoterpenoid
Benzyloxycarbonyl
Monocyclic monoterpenoid
Monoterpenoid
Phenoxy compound
Phenol ether
Monocyclic benzene moiety
Cyclopropanecarboxylic acid or derivatives
Benzenoid
Carboxylic acid ester
Ether
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

cyclopropanes (CHEBI:34916 )
Pyrethroid insecticides (C14387 )

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	6.42	ALOGPS
logP	5.57	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	103.84 m³·mol⁻¹	ChemAxon
Polarizability	39.2 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DB13717

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB007353

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C14387

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phenothrin

METLIN ID

Not Available

PubChem Compound

4767

PDB ID

Not Available

ChEBI ID

34916

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Fenugrin A (NP0047115)

MOL for NP0047115 (Fenugrin A)

3D MOL for NP0047115 (Fenugrin A)

3D SDF for NP0047115 (Fenugrin A)

3D-SDF for NP0047115 (Fenugrin A)

PDB for NP0047115 (Fenugrin A)

3D PDB for NP0047115 (Fenugrin A)

SMILES for NP0047115 (Fenugrin A)

INCHI for NP0047115 (Fenugrin A)

Structure for NP0047115 (Fenugrin A)

3D Structure for NP0047115 (Fenugrin A)