NP-MRD: Showing NP-Card for 3-chloro-4-hydroxyphenylacetic acid (NP0027850)

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Record Information

Version

1.0

Created at

2021-06-19 19:53:43 UTC

Updated at

2021-06-29 23:54:14 UTC

NP-MRD ID

NP0027850

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-chloro-4-hydroxyphenylacetic acid

Provided By

JEOL Database JEOL Logo

Description

(3-Chloro-4-hydroxyphenyl)acetic acid is also known as 3-chloro-4-hydroxybenzeneacetate (3-chloro-4-hydroxyphenyl)acetic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 3-chloro-4-hydroxyphenylacetic acid is found in Xylaria sp. It was first documented in 2002 (PMID: 12076687). Based on a literature review a small amount of articles have been published on (3-chloro-4-hydroxyphenyl)acetic acid (PMID: 17686770) (PMID: 20595238) (PMID: 23067249).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192121533D          

 19 19  0  0  0  0            999 V2000
    0.3918   -0.6880   -0.3573 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4084   -1.8438   -0.7441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9678   -2.1481   -1.9354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1204   -3.0721   -0.0448 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8478   -2.7747    1.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2438   -2.6256    1.2581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9173   -2.3379    2.4475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1986   -2.1912    3.6279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9045   -1.9098    4.7653 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8098   -2.3277    3.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0831   -2.1431    5.0944 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.1335   -2.6169    2.4447 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2711   -1.2810   -2.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7221   -3.7426    0.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7978   -3.5955   -0.7301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8193   -2.7293    0.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9979   -2.2241    2.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2556   -1.8203    5.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9497   -2.7132    2.4524 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  5  4  1  0  0  0  0
  8 10  1  0  0  0  0
  4  2  1  0  0  0  0
  2  1  2  0  0  0  0
 10 12  2  0  0  0  0
  2  3  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 12  5  1  0  0  0  0
 10 11  1  0  0  0  0
  6 16  1  0  0  0  0
  7 17  1  0  0  0  0
 12 19  1  0  0  0  0
  4 14  1  0  0  0  0
  4 15  1  0  0  0  0
  3 13  1  0  0  0  0
  9 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0027850

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])C1=C([H])C([H])=C(O[H])C(Cl)=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C8H7ClO3/c9-6-3-5(4-8(11)12)1-2-7(6)10/h1-3,10H,4H2,(H,11,12)

> <INCHI_KEY>
IYTUKSIOQKTZEG-UHFFFAOYSA-N

> <FORMULA>
C8H7ClO3

> <MOLECULAR_WEIGHT>
186.592

> <EXACT_MASS>
186.008371797

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
17.156201086012498

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(3-chloro-4-hydroxyphenyl)acetic acid

> <ALOGPS_LOGP>
1.82

> <JCHEM_LOGP>
1.9114734599999998

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.942788013834612

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4583466523526467

> <JCHEM_PKA_STRONGEST_BASIC>
-6.727893726983543

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
44.151300000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.54e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3-chloro-4-hydroxyphenyl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  O   UNK     0       0.392  -0.688  -0.357  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.408  -1.844  -0.744  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.968  -2.148  -1.935  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.120  -3.072  -0.045  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.848  -2.775   1.246  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.244  -2.626   1.258  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.917  -2.338   2.447  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.199  -2.191   3.628  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.905  -1.910   4.765  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.810  -2.328   3.631  0.00  0.00           C+0
HETATM   11 Cl   UNK     0       0.083  -2.143   5.094  0.00  0.00          Cl+0
HETATM   12  C   UNK     0      -0.134  -2.617   2.445  0.00  0.00           C+0
HETATM   13  H   UNK     0       1.271  -1.281  -2.280  0.00  0.00           H+0
HETATM   14  H   UNK     0       0.722  -3.743   0.162  0.00  0.00           H+0
HETATM   15  H   UNK     0      -0.798  -3.595  -0.730  0.00  0.00           H+0
HETATM   16  H   UNK     0      -2.819  -2.729   0.340  0.00  0.00           H+0
HETATM   17  H   UNK     0      -3.998  -2.224   2.452  0.00  0.00           H+0
HETATM   18  H   UNK     0      -2.256  -1.820   5.488  0.00  0.00           H+0
HETATM   19  H   UNK     0       0.950  -2.713   2.452  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    4    1    3                                                  
CONECT    3    2   13                                                       
CONECT    4    5    2   14   15                                             
CONECT    5    6    4   12                                                  
CONECT    6    5    7   16                                                  
CONECT    7    6    8   17                                                  
CONECT    8   10    7    9                                                  
CONECT    9    8   18                                                       
CONECT   10    8   12   11                                                  
CONECT   11   10                                                            
CONECT   12   10    5   19                                                  
CONECT   13    3                                                            
CONECT   14    4                                                            
CONECT   15    4                                                            
CONECT   16    6                                                            
CONECT   17    7                                                            
CONECT   18    9                                                            
CONECT   19   12                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
3-Chloro-4-hydroxybenzeneacetic acid	ChEBI
3-Chloro-4-hydroxyphenylacetic acid	ChEBI
3-Chloro-4-hydroxybenzeneacetate	Generator
3-Chloro-4-hydroxyphenylacetate	Generator
(3-Chloro-4-hydroxyphenyl)acetate	Generator
3-chloro-4-Hydroxyphenylacetic acid, monosodium salt	MeSH

Chemical Formula

C₈H₇ClO₃

Average Mass

186.5920 Da

Monoisotopic Mass

186.00837 Da

IUPAC Name

2-(3-chloro-4-hydroxyphenyl)acetic acid

Traditional Name

(3-chloro-4-hydroxyphenyl)acetic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C([H])([H])C1=C([H])C([H])=C(O[H])C(Cl)=C1[H]

InChI Identifier

InChI=1S/C8H7ClO3/c9-6-3-5(4-8(11)12)1-2-7(6)10/h1-3,10H,4H2,(H,11,12)

InChI Key

IYTUKSIOQKTZEG-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Xylaria sp.	JEOL database	Davis, R. A., et al, Tetrahedron Letts. 46, 919 (2005)

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as o-chlorophenols. These are chlorophenols carrying a iodine at the C2 position of the benzene ring.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

2-chlorophenol
1-hydroxy-2-unsubstituted benzenoid
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Organohalogen compound
Organochloride
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:47106 )
monochlorobenzenes (CHEBI:47106 )
hydroxy monocarboxylic acid (CHEBI:47106 )

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	1.82	ALOGPS
logP	1.91	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	3.46	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	44.15 m³·mol⁻¹	ChemAxon
Polarizability	17.16 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

105942

KEGG Compound ID

Not Available

BioCyc ID

CPD-10862

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

47106

Good Scents ID

Not Available

References

General References

Mani AR, Ippolito S, Moreno JC, Visser TJ, Moore KP: The metabolism and dechlorination of chlorotyrosine in vivo. J Biol Chem. 2007 Oct 5;282(40):29114-21. doi: 10.1074/jbc.M704270200. Epub 2007 Aug 8. [PubMed:17686770 ]
Lankova M, Smith RS, Pesek B, Kubes M, Zazimalova E, Petrasek J, Hoyerova K: Auxin influx inhibitors 1-NOA, 2-NOA, and CHPAA interfere with membrane dynamics in tobacco cells. J Exp Bot. 2010 Aug;61(13):3589-98. doi: 10.1093/jxb/erq172. Epub 2010 Jul 1. [PubMed:20595238 ]
Meng ZB, You XD, Suo D, Chen YL, Tang C, Yang JL, Zheng SJ: Root-derived auxin contributes to the phosphorus-deficiency-induced cluster-root formation in white lupin (Lupinus albus). Physiol Plant. 2013 Aug;148(4):481-9. doi: 10.1111/j.1399-3054.2012.01715.x. Epub 2012 Nov 20. [PubMed:23067249 ]
Laurens JB, Mbianda XY, Spies JH, Ubbink JB, Vermaak WJ: Validated method for quantitation of biomarkers for benzene and its alkylated analogues in urine. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Jul 15;774(2):173-85. doi: 10.1016/s1570-0232(02)00206-4. [PubMed:12076687 ]
Davis, R. A., et al. (2005). Davis, R. A., et al, Tetrahedron Letts. 46, 919 (2005). Tetrahedron Lett.

Showing NP-Card for 3-chloro-4-hydroxyphenylacetic acid (NP0027850)

MOL for NP0027850 (3-chloro-4-hydroxyphenylacetic acid)

3D MOL for NP0027850 (3-chloro-4-hydroxyphenylacetic acid)

3D SDF for NP0027850 (3-chloro-4-hydroxyphenylacetic acid)

3D-SDF for NP0027850 (3-chloro-4-hydroxyphenylacetic acid)

PDB for NP0027850 (3-chloro-4-hydroxyphenylacetic acid)

3D PDB for NP0027850 (3-chloro-4-hydroxyphenylacetic acid)

SMILES for NP0027850 (3-chloro-4-hydroxyphenylacetic acid)

INCHI for NP0027850 (3-chloro-4-hydroxyphenylacetic acid)

Structure for NP0027850 (3-chloro-4-hydroxyphenylacetic acid)

3D Structure for NP0027850 (3-chloro-4-hydroxyphenylacetic acid)