NP-MRD: Showing NP-Card for Sertraline (NP0334585)

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Record Information

Version

2.0

Created at

2024-09-10 19:01:23 UTC

Updated at

2024-09-10 19:01:24 UTC

NP-MRD ID

NP0334585

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sertraline

Description

Sertraline, also known as CP 51974 or zoloft, belongs to the class of organic compounds known as tametralines. Tametralines are compounds containing a tametraline moiety, which consists of a tetrahydronaphthalene linked to a phenyl group to form N-methyl-4-phenyl-1,2,3,4-tetrahydronaphthalen-1-amine skeleton. Sertraline is a very strong basic compound (based on its pKa). Sertraline was first documented in 1996 (PMID: 8645336). Sertraline is a potentially toxic compound (PMID: 15932816) (PMID: 16213473) (PMID: 10831484) (PMID: 15547048).

Structure

MOL SDF PDB SMILES InChI

1104
  Mrv0541 02231215152D          

 20 22  0  0  1  0            999 V2000
    1.6498   -2.2685    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0786   -3.0934    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    2.6809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    0.2063    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3641    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    1.8561    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3641    1.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    1.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5304    0.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5304    1.8847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2778    0.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2778    1.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    3.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641   -1.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929   -1.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786   -2.2685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  2 20  1  0  0  0  0
  6  3  1  6  0  0  0
  3 17  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  4 10  1  6  0  0  0
  5  7  1  0  0  0  0
  6  7  1  0  0  0  0
  6  9  1  0  0  0  0
  8  9  1  0  0  0  0
  8 11  2  0  0  0  0
  9 12  2  0  0  0  0
 10 13  2  0  0  0  0
 10 14  1  0  0  0  0
 11 15  1  0  0  0  0
 12 16  1  0  0  0  0
 13 18  1  0  0  0  0
 14 19  2  0  0  0  0
 15 16  2  0  0  0  0
 18 20  2  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334585

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN[C@H]1CC[C@@H](C2=CC(Cl)=C(Cl)C=C2)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C17H17Cl2N/c1-20-17-9-7-12(13-4-2-3-5-14(13)17)11-6-8-15(18)16(19)10-11/h2-6,8,10,12,17,20H,7,9H2,1H3/t12-,17-/m0/s1

> <INCHI_KEY>
VGKDLMBJGBXTGI-SJCJKPOMSA-N

> <FORMULA>
C17H17Cl2N

> <MOLECULAR_WEIGHT>
306.23

> <EXACT_MASS>
305.073804963

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
32.442850025091104

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine

> <ALOGPS_LOGP>
5.06

> <JCHEM_LOGP>
5.1492999736666665

> <ALOGPS_LOGS>
-6.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.853307918944921

> <JCHEM_POLAR_SURFACE_AREA>
12.03

> <JCHEM_REFRACTIVITY>
85.741

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.45e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sertraline

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1104                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       3.080  -4.235   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0       5.747  -5.774   0.000  0.00  0.00          Cl+0
HETATM    3  N   UNK     0       5.747   5.004   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       5.747   0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.413   1.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.747   3.465   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.413   2.695   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.080   1.155   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.080   2.695   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.747  -1.155   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.457   0.331   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.457   3.518   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.413  -1.925   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.080  -1.925   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.852   1.123   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.852   2.727   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.413   5.774   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.413  -3.465   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.080  -3.465   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.747  -4.235   0.000  0.00  0.00           C+0
CONECT    1   18                                                            
CONECT    2   20                                                            
CONECT    3    6   17                                                       
CONECT    4    5    8   10                                                  
CONECT    5    4    7                                                       
CONECT    6    3    7    9                                                  
CONECT    7    5    6                                                       
CONECT    8    4    9   11                                                  
CONECT    9    6    8   12                                                  
CONECT   10    4   13   14                                                  
CONECT   11    8   15                                                       
CONECT   12    9   16                                                       
CONECT   13   10   18                                                       
CONECT   14   10   19                                                       
CONECT   15   11   16                                                       
CONECT   16   12   15                                                       
CONECT   17    3                                                            
CONECT   18    1   13   20                                                  
CONECT   19   14   20                                                       
CONECT   20    2   18   19                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
(+)-Sertraline	ChEBI
(1S,4S)-Sertraline	ChEBI
(1S-cis)-1,2,3,4-Tetrahydro-4-(3,4-dichlorophenyl)-N-methyl-1-naphthalenamine	ChEBI
cis-(+)-Sertraline	ChEBI
CP 51974	ChEBI
Sertralina	ChEBI
Sertralinum	ChEBI
Sertraline hydrochloride	HMDB
Zoloft	HMDB
Besitran	HMDB
Gen sertraline	HMDB
Novo sertraline	HMDB
Parke davis brand OF sertraline hydrochloride	HMDB
Ratiopharm brand OF sertraline hydrochloride	HMDB
Rhoxal sertraline	HMDB
Sertraline hydrochloride (1S-cis)-isomer	HMDB
Altruline	HMDB
Lustral	HMDB
Novo-sertraline	HMDB
Rhoxalpharma brand OF sertraline hydrochloride	HMDB
Roerig brand OF sertraline hydrochloride	HMDB
Sealdin	HMDB
Ratio sertraline	HMDB
Ratio-sertraline	HMDB
Apo sertraline	HMDB
Apo-sertraline	HMDB
Aremis	HMDB
Boehringer ingelheim brand OF sertraline hydrochloride	HMDB
Gladem	HMDB
Pfizer brand OF sertraline hydrochloride	HMDB
Apotex brand OF sertraline hydrochloride	HMDB
Esteve brand OF sertraline hydrochloride	HMDB
Gen-sertraline	HMDB
Genpharm brand OF sertraline hydrochloride	HMDB
Hydrochloride, sertraline	HMDB
Lacer brand OF sertraline hydrochloride	HMDB
Novopharm brand OF sertraline hydrochloride	HMDB
Rhoxal-sertraline	HMDB

Chemical Formula

C₁₇H₁₇Cl₂N

Average Mass

306.2300 Da

Monoisotopic Mass

305.07380 Da

IUPAC Name

(1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine

Traditional Name

sertraline

CAS Registry Number

Not Available

SMILES

CN[C@H]1CC[C@@H](C2=CC(Cl)=C(Cl)C=C2)C2=CC=CC=C12

InChI Identifier

InChI=1S/C17H17Cl2N/c1-20-17-9-7-12(13-4-2-3-5-14(13)17)11-6-8-15(18)16(19)10-11/h2-6,8,10,12,17,20H,7,9H2,1H3/t12-,17-/m0/s1

InChI Key

VGKDLMBJGBXTGI-SJCJKPOMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tametralines. Tametralines are compounds containing a tametraline moiety, which consists of a tetrahydronaphthalene linked to a phenyl group to form N-methyl-4-phenyl-1,2,3,4-tetrahydronaphthalen-1-amine skeleton.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Tametraline
1,2-dichlorobenzene
Chlorobenzene
Halobenzene
Aralkylamine
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Secondary aliphatic amine
Secondary amine
Organohalogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Amine
Organochloride
Organonitrogen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

secondary amino compound (CHEBI:9123 )
dichlorobenzene (CHEBI:9123 )
tetralins (CHEBI:9123 )

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	5.06	ALOGPS
logP	5.15	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Basic)	9.85	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	12.03 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	85.74 m³·mol⁻¹	ChemAxon
Polarizability	32.44 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	No	ChemAxon

External Links

HMDB ID

HMDB0005010

DrugBank ID

DB01104

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023583

KNApSAcK ID

Not Available

Chemspider ID

61881

KEGG Compound ID

C07246

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

ChEBI ID

Good Scents ID

Not Available

References

General References

Agnel M, Esnaud H, Langer SZ, Graham D: Pharmacological characterization of the cloned human 5-hydroxytryptamine transporter. Biochem Pharmacol. 1996 May 3;51(9):1145-51. doi: 10.1016/0006-2952(96)00028-7. [PubMed:8645336 ]
Serebruany VL, Suckow RF, Cooper TB, O'Connor CM, Malinin AI, Krishnan KR, van Zyl LT, Lekht V, Glassman AH: Relationship between release of platelet/endothelial biomarkers and plasma levels of sertraline and N-desmethylsertraline in acute coronary syndrome patients receiving SSRI treatment for depression. Am J Psychiatry. 2005 Jun;162(6):1165-70. doi: 10.1176/appi.ajp.162.6.1165. [PubMed:15932816 ]
Parsey RV, Kent JM, Oquendo MA, Richards MC, Pratap M, Cooper TB, Arango V, Mann JJ: Acute occupancy of brain serotonin transporter by sertraline as measured by [11C]DASB and positron emission tomography. Biol Psychiatry. 2006 May 1;59(9):821-8. doi: 10.1016/j.biopsych.2005.08.010. Epub 2005 Oct 6. [PubMed:16213473 ]
Markovitz JH, Shuster JL, Chitwood WS, May RS, Tolbert LC: Platelet activation in depression and effects of sertraline treatment: An open-label study. Am J Psychiatry. 2000 Jun;157(6):1006-8. doi: 10.1176/appi.ajp.157.6.1006. [PubMed:10831484 ]
Obach RS, Cox LM, Tremaine LM: Sertraline is metabolized by multiple cytochrome P450 enzymes, monoamine oxidases, and glucuronyl transferases in human: an in vitro study. Drug Metab Dispos. 2005 Feb;33(2):262-70. doi: 10.1124/dmd.104.002428. Epub 2004 Nov 16. [PubMed:15547048 ]

Showing NP-Card for Sertraline (NP0334585)

MOL for NP0334585 (Sertraline)

3D MOL for NP0334585 (Sertraline)

3D SDF for NP0334585 (Sertraline)

3D-SDF for NP0334585 (Sertraline)

PDB for NP0334585 (Sertraline)

3D PDB for NP0334585 (Sertraline)

SMILES for NP0334585 (Sertraline)

INCHI for NP0334585 (Sertraline)

Structure for NP0334585 (Sertraline)

3D Structure for NP0334585 (Sertraline)