NP-MRD: Showing NP-Card for 2,4,4'-trichloro-2'-hydroxydiphenylethe (NP0023876)

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Record Information

Version

1.0

Created at

2021-01-06 08:54:26 UTC

Updated at

2021-08-20 00:00:06 UTC

NP-MRD ID

NP0023876

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,4,4'-trichloro-2'-hydroxydiphenylethe

Provided By

NPAtlas

Description

Triclosan, also known as irgasan DP 300 or aquasept, belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group. 2,4,4'-trichloro-2'-hydroxydiphenylethe is found in Micrococcus luteus. It was first documented in 1998 (PMID: 9852617). Based on a literature review a significant number of articles have been published on Triclosan (PMID: 11175846) (PMID: 11418506) (PMID: 15269185) (PMID: 17567585).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242121053D          

 24 25  0  0  0  0            999 V2000
   -1.7947    2.3862   -0.2444 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1170    1.0834   -0.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4881    0.8069   -0.0923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9842   -0.4417    0.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7320   -0.6992    0.0650 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1288   -1.5200    0.0903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7935   -1.2756    0.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2302    0.0361   -0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0435    0.0629   -0.0860 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3290    0.0899   -0.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9937   -1.1918    0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3394   -1.3270    0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1496   -0.2214   -0.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8856   -0.3765   -0.1195 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5776    1.0125   -0.2324 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1763    1.1580   -0.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5011    2.7573   -0.3968 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2077    3.0792   -0.3064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1817    1.6568   -0.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5526   -2.5230    0.1775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1393   -2.1309    0.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3339   -2.0435    0.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8472   -2.2930    0.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1728    1.9142   -0.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
  8  2  1  0  0  0  0
 16 10  1  0  0  0  0
  1 18  1  0  0  0  0
  3 19  1  0  0  0  0
  6 20  1  0  0  0  0
  7 21  1  0  0  0  0
 11 22  1  0  0  0  0
 12 23  1  0  0  0  0
 15 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0023876

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(Cl)=C([H])C([H])=C1OC1=C([H])C([H])=C(Cl)C([H])=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C12H7Cl3O2/c13-7-1-3-11(9(15)5-7)17-12-4-2-8(14)6-10(12)16/h1-6,16H

> <INCHI_KEY>
XEFQLINVKFYRCS-UHFFFAOYSA-N

> <FORMULA>
C12H7Cl3O2

> <MOLECULAR_WEIGHT>
289.542

> <EXACT_MASS>
287.951162589

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
25.92401369691182

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-chloro-2-(2,4-dichlorophenoxy)phenol

> <ALOGPS_LOGP>
5.53

> <JCHEM_LOGP>
4.982101706333333

> <ALOGPS_LOGS>
-4.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.680637141174448

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7626176476453383

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
68.6941

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.05e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
triclosan

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0      -1.795   2.386  -0.244  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.117   1.083  -0.135  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.488   0.807  -0.092  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.984  -0.442   0.016  0.00  0.00           C+0
HETATM    5 Cl   UNK     0      -5.732  -0.699   0.065  0.00  0.00          Cl+0
HETATM    6  C   UNK     0      -3.129  -1.520   0.090  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.794  -1.276   0.050  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.230   0.036  -0.064  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.044   0.063  -0.086  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.329   0.090  -0.108  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.994  -1.192   0.013  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.339  -1.327   0.009  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.150  -0.221  -0.115  0.00  0.00           C+0
HETATM   14 Cl   UNK     0       5.886  -0.377  -0.120  0.00  0.00          Cl+0
HETATM   15  C   UNK     0       3.578   1.012  -0.232  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.176   1.158  -0.228  0.00  0.00           C+0
HETATM   17 Cl   UNK     0       1.501   2.757  -0.397  0.00  0.00          Cl+0
HETATM   18  H   UNK     0      -1.208   3.079  -0.306  0.00  0.00           H+0
HETATM   19  H   UNK     0      -4.182   1.657  -0.152  0.00  0.00           H+0
HETATM   20  H   UNK     0      -3.553  -2.523   0.178  0.00  0.00           H+0
HETATM   21  H   UNK     0      -1.139  -2.131   0.109  0.00  0.00           H+0
HETATM   22  H   UNK     0       1.334  -2.043   0.109  0.00  0.00           H+0
HETATM   23  H   UNK     0       3.847  -2.293   0.101  0.00  0.00           H+0
HETATM   24  H   UNK     0       4.173   1.914  -0.334  0.00  0.00           H+0
CONECT    1    2   18                                                       
CONECT    2    1    3    8                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   20                                                  
CONECT    7    6    8   21                                                  
CONECT    8    7    9    2                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12   22                                                  
CONECT   12   11   13   23                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   24                                                  
CONECT   16   15   17   10                                                  
CONECT   17   16                                                            
CONECT   18    1                                                            
CONECT   19    3                                                            
CONECT   20    6                                                            
CONECT   21    7                                                            
CONECT   22   11                                                            
CONECT   23   12                                                            
CONECT   24   15                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
2,4,4'-Trichloro-2'-hydroxydiphenyl ether	ChEBI
5-Chloro-2-(2,4-dichloro-phenoxy)-phenol	ChEBI
Triclosanum	ChEBI
Stri-dex cleansing bar	Kegg
Aquasept	HMDB
Irgasan DP 300	HMDB
2-Hydroxy-2',4,4'-trichlorodiphenyl ether	HMDB
Pharmachem brand OF triclosan	HMDB
Procter and gamble brand OF triclosan	HMDB
Tersaseptic	HMDB
GlaxoSmithKline brand OF triclosan	HMDB
Irgasan DP300	HMDB
Irgasan-DP300	HMDB
Sapoderm	HMDB
SterZac bath concentrate	HMDB
Trisan	HMDB
Triclosan pharmachem brand	HMDB
Clearasil daily face wash	HMDB
Cliniclean	HMDB
DP300, Irgasan	HMDB
Dermtek brand OF triclosan	HMDB
Johnson and johnson brand OF triclosan	HMDB
Manusept	HMDB
Microshield T	HMDB
Oxy skin wash	HMDB
Reckitt brand OF triclosan	HMDB
SSL Brand OF triclosan	HMDB
Ster zac bath concentrate	HMDB
Ster-zac bath concentrate	HMDB
trans Canaderm brand OF triclosan	HMDB
Triclosan reckitt brand	HMDB
PHisoHex	HMDB

Chemical Formula

C₁₂H₇Cl₃O₂

Average Mass

289.5420 Da

Monoisotopic Mass

287.95116 Da

IUPAC Name

5-chloro-2-(2,4-dichlorophenoxy)phenol

Traditional Name

triclosan

CAS Registry Number

Not Available

SMILES

OC1=C(OC2=C(Cl)C=C(Cl)C=C2)C=CC(Cl)=C1

InChI Identifier

InChI=1S/C12H7Cl3O2/c13-7-1-3-11(9(15)5-7)17-12-4-2-8(14)6-10(12)16/h1-6,16H

InChI Key

XEFQLINVKFYRCS-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
Micrococcus luteus	NPAtlas	9852617

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylethers

Direct Parent

Diphenylethers

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	54.00 to 58.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	344.00 to 345.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	10 mg/L @ 20 °C (exp)	The Good Scents Company Information System
LogP	4.760	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	5.53	ALOGPS
logP	4.98	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	7.68	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	68.69 m³·mol⁻¹	ChemAxon
Polarizability	25.92 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

NPAtlas ID

NPA011823

HMDB ID

HMDB0061385

DrugBank ID

DB08604

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5363

KEGG Compound ID

C12059

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Triclosan

METLIN ID

Not Available

PubChem Compound

5564

PDB ID

Not Available

ChEBI ID

164200

Good Scents ID

rw1304041

References

General References

Bultel-Ponce V V, Debitus C, Berge JP, Cerceau C, Guyot M: Metabolites from the sponge-associated bacterium Micrococcus luteus. J Mar Biotechnol. 1998 Dec;6(4):233-236. [PubMed:9852617 ]
Surolia N, Surolia A: Triclosan offers protection against blood stages of malaria by inhibiting enoyl-ACP reductase of Plasmodium falciparum. Nat Med. 2001 Feb;7(2):167-73. doi: 10.1038/84612. [PubMed:11175846 ]
Slater-Radosti C, Van Aller G, Greenwood R, Nicholas R, Keller PM, DeWolf WE Jr, Fan F, Payne DJ, Jaworski DD: Biochemical and genetic characterization of the action of triclosan on Staphylococcus aureus. J Antimicrob Chemother. 2001 Jul;48(1):1-6. doi: 10.1093/jac/48.1.1. [PubMed:11418506 ]
Wang LQ, Falany CN, James MO: Triclosan as a substrate and inhibitor of 3'-phosphoadenosine 5'-phosphosulfate-sulfotransferase and UDP-glucuronosyl transferase in human liver fractions. Drug Metab Dispos. 2004 Oct;32(10):1162-9. doi: 10.1124/dmd.104.000273. Epub 2004 Jul 21. [PubMed:15269185 ]
Freundlich JS, Wang F, Tsai HC, Kuo M, Shieh HM, Anderson JW, Nkrumah LJ, Valderramos JC, Yu M, Kumar TR, Valderramos SG, Jacobs WR Jr, Schiehser GA, Jacobus DP, Fidock DA, Sacchettini JC: X-ray structural analysis of Plasmodium falciparum enoyl acyl carrier protein reductase as a pathway toward the optimization of triclosan antimalarial efficacy. J Biol Chem. 2007 Aug 31;282(35):25436-44. doi: 10.1074/jbc.M701813200. Epub 2007 Jun 13. [PubMed:17567585 ]

Showing NP-Card for 2,4,4'-trichloro-2'-hydroxydiphenylethe (NP0023876)

MOL for NP0023876 (2,4,4'-trichloro-2'-hydroxydiphenylethe)

3D MOL for NP0023876 (2,4,4'-trichloro-2'-hydroxydiphenylethe)

3D SDF for NP0023876 (2,4,4'-trichloro-2'-hydroxydiphenylethe)

3D-SDF for NP0023876 (2,4,4'-trichloro-2'-hydroxydiphenylethe)

PDB for NP0023876 (2,4,4'-trichloro-2'-hydroxydiphenylethe)

3D PDB for NP0023876 (2,4,4'-trichloro-2'-hydroxydiphenylethe)

SMILES for NP0023876 (2,4,4'-trichloro-2'-hydroxydiphenylethe)

INCHI for NP0023876 (2,4,4'-trichloro-2'-hydroxydiphenylethe)

Structure for NP0023876 (2,4,4'-trichloro-2'-hydroxydiphenylethe)

3D Structure for NP0023876 (2,4,4'-trichloro-2'-hydroxydiphenylethe)