NP-MRD: Showing NP-Card for fluoxetine (NP0166766)

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Record Information

Version

2.0

Created at

2022-09-03 02:12:18 UTC

Updated at

2022-09-03 02:12:19 UTC

NP-MRD ID

NP0166766

Secondary Accession Numbers

None

Natural Product Identification

Common Name

fluoxetine

Description

Fluoxetine, also known as sarafem or symbyax, belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups. Fluoxetine is a very strong basic compound (based on its pKa). Fluoxetine can be converted into norfluoxetine and formaldehyde; which is mediated by the enzymes cytochrome P450 3A5, cytochrome P450 3A4, cytochrome P450 2C9, cytochrome P450 2C19, and cytochrome P450 2D6. In humans, fluoxetine is involved in fluoxetine metabolism pathway. An aromatic ether consisting of 4-trifluoromethylphenol in which the hydrogen of the phenolic hydroxy group is replaced by a 3-(methylamino)-1-phenylpropyl group. fluoxetine is found in Hordeum vulgare. fluoxetine was first documented in 1995 (PMID: 7623609). Fluoxetine is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

472
  Mrv0541 02231214422D          

 22 23  0  0  1  0            999 V2000
    4.3974    2.6813    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.0475    2.6813    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.5063    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.6188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 22  1  0  0  0  0
  2 22  1  0  0  0  0
  3 22  1  0  0  0  0
  4  6  1  0  0  0  0
  4 12  1  0  0  0  0
  5  9  1  0  0  0  0
  5 19  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  2  0  0  0  0
  8 11  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  2  0  0  0  0
 12 15  2  0  0  0  0
 12 16  1  0  0  0  0
 13 18  2  0  0  0  0
 14 18  1  0  0  0  0
 15 20  1  0  0  0  0
 16 21  2  0  0  0  0
 17 20  2  0  0  0  0
 17 21  1  0  0  0  0
 17 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0166766

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CNCCC(OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H18F3NO/c1-21-12-11-16(13-5-3-2-4-6-13)22-15-9-7-14(8-10-15)17(18,19)20/h2-10,16,21H,11-12H2,1H3

> <INCHI_KEY>
RTHCYVBBDHJXIQ-UHFFFAOYSA-N

> <FORMULA>
C17H18F3NO

> <MOLECULAR_WEIGHT>
309.3261

> <EXACT_MASS>
309.134048818

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
30.326618157922514

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl({3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl})amine

> <ALOGPS_LOGP>
4.09

> <JCHEM_LOGP>
4.1732195433333334

> <ALOGPS_LOGS>
-5.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.80313944120745

> <JCHEM_POLAR_SURFACE_AREA>
21.259999999999998

> <JCHEM_REFRACTIVITY>
80.36750000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.70e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fluoxetine

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 472                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  F   UNK     0       8.208   5.005   0.000  0.00  0.00           F+0
HETATM    2  F   UNK     0      11.289   5.005   0.000  0.00  0.00           F+0
HETATM    3  F   UNK     0       9.748   6.545   0.000  0.00  0.00           F+0
HETATM    4  O   UNK     0       9.748  -1.155   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       4.414  -1.155   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       8.415  -1.925   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081  -1.155   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.415  -3.465   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.748  -1.925   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.748  -4.235   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081  -4.235   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.748   0.385   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.748  -5.775   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081  -5.775   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.082   1.155   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.415   1.155   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.748   3.465   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.415  -6.545   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.080  -1.925   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.082   2.695   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.415   2.695   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.748   5.005   0.000  0.00  0.00           C+0
CONECT    1   22                                                            
CONECT    2   22                                                            
CONECT    3   22                                                            
CONECT    4    6   12                                                       
CONECT    5    9   19                                                       
CONECT    6    4    7    8                                                  
CONECT    7    6    9                                                       
CONECT    8    6   10   11                                                  
CONECT    9    5    7                                                       
CONECT   10    8   13                                                       
CONECT   11    8   14                                                       
CONECT   12    4   15   16                                                  
CONECT   13   10   18                                                       
CONECT   14   11   18                                                       
CONECT   15   12   20                                                       
CONECT   16   12   21                                                       
CONECT   17   20   21   22                                                  
CONECT   18   13   14                                                       
CONECT   19    5                                                            
CONECT   20   15   17                                                       
CONECT   21   16   17                                                       
CONECT   22    1    2    3   17                                             
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
Sarafem	HMDB
Symbyax	HMDB
Prozac	HMDB
Fluoxetine hydrochloride	HMDB
N-Methyl-gamma-(4-(trifluoromethyl)phenoxy)benzenepropanamine	HMDB
Fluoxetin	HMDB

Chemical Formula

C₁₇H₁₈F₃NO

Average Mass

309.3261 Da

Monoisotopic Mass

309.13405 Da

IUPAC Name

methyl({3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl})amine

Traditional Name

fluoxetine

CAS Registry Number

Not Available

SMILES

CNCCC(OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1

InChI Identifier

InChI=1S/C17H18F3NO/c1-21-12-11-16(13-5-3-2-4-6-13)22-15-9-7-14(8-10-15)17(18,19)20/h2-10,16,21H,11-12H2,1H3

InChI Key

RTHCYVBBDHJXIQ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Hordeum vulgare	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Trifluoromethylbenzenes

Direct Parent

Trifluoromethylbenzenes

Alternative Parents

Substituents

Trifluoromethylbenzene
Phenoxy compound
Phenol ether
Alkyl aryl ether
Aralkylamine
Secondary aliphatic amine
Ether
Secondary amine
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Alkyl fluoride
Organic nitrogen compound
Amine
Alkyl halide
Organopnictogen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:86990 )
secondary amino compound (CHEBI:86990 )
(trifluoromethyl)benzenes (CHEBI:86990 )

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	4.09	ALOGPS
logP	4.17	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Basic)	9.8	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	21.26 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	80.37 m³·mol⁻¹	ChemAxon
Polarizability	30.33 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0014615

DrugBank ID

DB00472

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3269

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fluoxetine

METLIN ID

Not Available

PubChem Compound

3386

PDB ID

Not Available

ChEBI ID

86990

Good Scents ID

Not Available

References

General References

Wong DT, Bymaster FP, Engleman EA: Prozac (fluoxetine, Lilly 110140), the first selective serotonin uptake inhibitor and an antidepressant drug: twenty years since its first publication. Life Sci. 1995;57(5):411-41. doi: 10.1016/0024-3205(95)00209-o. [PubMed:7623609 ]
LOTUS database [Link]

Showing NP-Card for fluoxetine (NP0166766)

MOL for NP0166766 (fluoxetine)

3D MOL for NP0166766 (fluoxetine)

3D SDF for NP0166766 (fluoxetine)

3D-SDF for NP0166766 (fluoxetine)

PDB for NP0166766 (fluoxetine)

3D PDB for NP0166766 (fluoxetine)

SMILES for NP0166766 (fluoxetine)

INCHI for NP0166766 (fluoxetine)

Structure for NP0166766 (fluoxetine)

3D Structure for NP0166766 (fluoxetine)