NP-MRD: Showing NP-Card for Fexofenadine (NP0087340)

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Record Information

Version

2.0

Created at

2022-05-11 16:46:59 UTC

Updated at

2022-05-11 16:47:00 UTC

NP-MRD ID

NP0087340

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Fexofenadine

Description

Fexofenadine, also known as terfenadine-COOH or telfast, belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. Fexofenadine is a very strong basic compound (based on its pKa). A piperidine-based anti-histamine compound. In humans, fexofenadine is involved in fexofenadine h1-antihistamine action. Fexofenadine is found in Streptomyces platensis. Fexofenadine was first documented in 1999 (PMID: 10421612). Fexofenadine is a potentially toxic compound (PMID: 12417888) (PMID: 15286093) (PMID: 11345280) (PMID: 12443840).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309201717592D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309201717592D          

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  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  7 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  8 13  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
  9 20  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 25 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 32 36  1  0  0  0  0
 32 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0087340

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(C(O)=O)C1=CC=C(C=C1)C(O)CCCN1CCC(CC1)C(O)(C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C32H39NO4/c1-31(2,30(35)36)25-17-15-24(16-18-25)29(34)14-9-21-33-22-19-28(20-23-33)32(37,26-10-5-3-6-11-26)27-12-7-4-8-13-27/h3-8,10-13,15-18,28-29,34,37H,9,14,19-23H2,1-2H3,(H,35,36)

> <INCHI_KEY>
RWTNPBWLLIMQHL-UHFFFAOYSA-N

> <FORMULA>
C32H39NO4

> <MOLECULAR_WEIGHT>
501.6564

> <EXACT_MASS>
501.287908741

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
57.42211230747313

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(4-{1-hydroxy-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]butyl}phenyl)-2-methylpropanoic acid

> <ALOGPS_LOGP>
5.02

> <JCHEM_LOGP>
2.9385009869991623

> <ALOGPS_LOGS>
-5.28

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.19564234596055

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.04043821405387

> <JCHEM_PKA_STRONGEST_BASIC>
9.010501448307204

> <JCHEM_POLAR_SURFACE_AREA>
80.99999999999999

> <JCHEM_REFRACTIVITY>
147.98460000000009

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.66e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fexofenadine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-SEP-17         0                                  
HETATM    1  C   UNK     0      15.645 -20.790   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.645 -22.330   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.979 -23.100   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.312 -22.330   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      18.312 -20.790   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.979 -20.020   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.980 -22.330   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.980 -20.790   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.646 -20.020   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.314 -23.100   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.647 -22.330   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.647 -20.790   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.314 -20.020   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.646 -18.479   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.982 -17.708   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.982 -16.168   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      19.648 -15.398   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      18.312 -16.169   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.312 -17.709   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      18.312 -19.250   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      19.648 -13.859   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      20.983 -13.089   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      22.298 -13.848   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      23.604 -13.095   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      24.915 -13.851   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      23.604 -11.549   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      24.915 -15.399   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      26.248 -16.169   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      27.582 -15.399   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      27.582 -13.852   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      26.249 -13.081   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      28.915 -16.169   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      30.229 -15.410   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      31.536 -16.164   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      30.230 -13.860   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      27.826 -17.258   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      30.004 -17.258   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    1                                                       
CONECT    7    8   10                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8    5   14   20                                             
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14    9   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20    9                                                            
CONECT   21   17   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24   27   31                                                  
CONECT   26   24                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30   25                                                       
CONECT   32   29   33   36   37                                             
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   32                                                            
CONECT   37   32                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-alpha,alpha-dimethylbenzeneacetic acid	ChEBI
Carboxyterfenadine	ChEBI
Terfenadine acid metabolite	ChEBI
Terfenadine carboxylate	ChEBI
Terfenadine-COOH	ChEBI
Telfast	Kegg
4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-a,a-dimethylbenzeneacetate	Generator
4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-a,a-dimethylbenzeneacetic acid	Generator
4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-alpha,alpha-dimethylbenzeneacetate	Generator
4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-α,α-dimethylbenzeneacetate	Generator
4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-α,α-dimethylbenzeneacetic acid	Generator
Terfenadine carboxylic acid	Generator
Allegra	HMDB
Fexofenadine hydrochloride	HMDB
Aventis pharma brand OF fexofenadine hydrochloride	HMDB
MDL 16,455a	HMDB
alpha-(4-(1-Carboxy-1-methylethyl)phenyl)-4-hydroxydiphenylmethyl-1-piperidinebutanol	HMDB
Aventis behring brand OF fexofenadine hydrochloride	HMDB
Aventis brand OF fexofenadine hydrochloride	HMDB
Hoechst brand OF fexofenadine hydrochloride	HMDB

Chemical Formula

C₃₂H₃₉NO₄

Average Mass

501.6564 Da

Monoisotopic Mass

501.28791 Da

IUPAC Name

2-(4-{1-hydroxy-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]butyl}phenyl)-2-methylpropanoic acid

Traditional Name

fexofenadine

CAS Registry Number

Not Available

SMILES

CC(C)(C(O)=O)C1=CC=C(C=C1)C(O)CCCN1CCC(CC1)C(O)(C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C32H39NO4/c1-31(2,30(35)36)25-17-15-24(16-18-25)29(34)14-9-21-33-22-19-28(20-23-33)32(37,26-10-5-3-6-11-26)27-12-7-4-8-13-27/h3-8,10-13,15-18,28-29,34,37H,9,14,19-23H2,1-2H3,(H,35,36)

InChI Key

RWTNPBWLLIMQHL-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Streptomyces platensis	LOTUS Database	35616633
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Phenylbutylamine
Phenylpropane
Aralkylamine
Piperidine
Tertiary alcohol
Amino acid or derivatives
Secondary alcohol
Amino acid
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Organic oxide
Amine
Carbonyl group
Aromatic alcohol
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

piperidines (CHEBI:5050 )
tertiary amine (CHEBI:5050 )

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	5.02	ALOGPS
logP	2.94	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.04	ChemAxon
pKa (Strongest Basic)	9.01	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	81 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	147.98 m³·mol⁻¹	ChemAxon
Polarizability	57.42 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0005030

DrugBank ID

DB00950

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023597

KNApSAcK ID

Not Available

Chemspider ID

3231

KEGG Compound ID

C06999

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fexofenadine

METLIN ID

2766

PubChem Compound

3348

PDB ID

Not Available

ChEBI ID

5050

Good Scents ID

Not Available

References

General References

Simons FE, Silver NA, Gu X, Simons KJ: Clinical pharmacology of H1-antihistamines in the skin. J Allergy Clin Immunol. 2002 Nov;110(5):777-83. [PubMed:12417888 ]
Cvetkovic M, Leake B, Fromm MF, Wilkinson GR, Kim RB: OATP and P-glycoprotein transporters mediate the cellular uptake and excretion of fexofenadine. Drug Metab Dispos. 1999 Aug;27(8):866-71. [PubMed:10421612 ]
Tashiro M, Sakurada Y, Iwabuchi K, Mochizuki H, Kato M, Aoki M, Funaki Y, Itoh M, Iwata R, Wong DF, Yanai K: Central effects of fexofenadine and cetirizine: measurement of psychomotor performance, subjective sleepiness, and brain histamine H1-receptor occupancy using 11C-doxepin positron emission tomography. J Clin Pharmacol. 2004 Aug;44(8):890-900. doi: 10.1177/0091270004267590. [PubMed:15286093 ]
Purohit A, Duvernelle C, Melac M, Pauli G, Frossard N: Twenty-four hours of activity of cetirizine and fexofenadine in the skin. Ann Allergy Asthma Immunol. 2001 Apr;86(4):387-92. doi: 10.1016/S1081-1206(10)62483-0. [PubMed:11345280 ]
Inoue T, Katoh N, Kishimoto S, Matsunaga K: Inhibitory effects of oral prednisolone and fexofenadine on skin responses by prick tests with histamine and compound 48/80. J Dermatol Sci. 2002 Dec;30(3):180-4. doi: 10.1016/s0923-1811(02)00069-5. [PubMed:12443840 ]

Showing NP-Card for Fexofenadine (NP0087340)

MOL for NP0087340 (Fexofenadine)

3D MOL for NP0087340 (Fexofenadine)

3D SDF for NP0087340 (Fexofenadine)

3D-SDF for NP0087340 (Fexofenadine)

PDB for NP0087340 (Fexofenadine)

3D PDB for NP0087340 (Fexofenadine)

SMILES for NP0087340 (Fexofenadine)

INCHI for NP0087340 (Fexofenadine)

Structure for NP0087340 (Fexofenadine)

3D Structure for NP0087340 (Fexofenadine)