NP-MRD: Showing NP-Card for 4-Chloro-1H-indole-3-acetic acid (NP0047496)

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Record Information

Version

2.0

Created at

2022-03-17 20:41:09 UTC

Updated at

2022-03-17 20:41:09 UTC

NP-MRD ID

NP0047496

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-Chloro-1H-indole-3-acetic acid

Description

4-Chloro-1H-indole-3-acetic acid, also known as 4-CL-iaa or 4-chloroindolyl-3-acetate, belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. 4-Chloro-1H-indole-3-acetic acid is a weakly acidic compound (based on its pKa). Outside of the human body, 4-Chloro-1H-indole-3-acetic acid has been detected, but not quantified in, several different foods, such as broad beans, common pea, grass pea, lentils, and pulses. 4-Chloro-1H-indole-3-acetic acid is found in Lathyrus latifolius, Lathyrus maritimus, Lathyrus odoratus , Pinus sylvestris , Vicia amurensis and Vicia sativa . This could make 4-chloro-1H-indole-3-acetic acid a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241219272D          

 14 15  0  0  0  0            999 V2000
   -0.5355    0.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1955   -0.0409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9380    0.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9380    1.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1955    1.6084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5355    1.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2880    1.4433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7830    0.7834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2880    0.1241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5355   -0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3605   -0.7834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9380   -0.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1955   -0.8659    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6080   -1.6084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  1  9  1  0  0  0  0
  2  3  2  0  0  0  0
  2 13  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047496

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CC1=CNC2=C1C(Cl)=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C10H8ClNO2/c11-7-2-1-3-8-10(7)6(5-12-8)4-9(13)14/h1-3,5,12H,4H2,(H,13,14)

> <INCHI_KEY>
WNCFBCKZRJDRKZ-UHFFFAOYSA-N

> <FORMULA>
C10H8ClNO2

> <MOLECULAR_WEIGHT>
209.629

> <EXACT_MASS>
209.024356212

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
19.922565451006136

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-chloro-1H-indol-3-yl)acetic acid

> <ALOGPS_LOGP>
2.30

> <JCHEM_LOGP>
2.3138007746666664

> <ALOGPS_LOGS>
-2.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.858821121357352

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.144646700106181

> <JCHEM_POLAR_SURFACE_AREA>
53.09

> <JCHEM_REFRACTIVITY>
53.25690000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-chloroindole-3-acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.000   0.692   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.232  -0.076   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.618   0.692   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.618   2.232   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.232   3.002   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.000   2.232   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.538   2.694   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.462   1.462   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.538   0.232   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.000  -1.154   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.540  -1.462   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.618  -0.384   0.000  0.00  0.00           O+0
HETATM   13 Cl   UNK     0      -2.232  -1.616   0.000  0.00  0.00          Cl+0
HETATM   14  O   UNK     0       3.002  -3.002   0.000  0.00  0.00           O+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    1    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11                                                            
CONECT   13    2                                                            
CONECT   14   11                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Value	Source
4-Chloroindolyl-3-acetic acid	ChEBI
4-CL-IAA	ChEBI
4-Chloroindolyl-3-acetate	Generator
4-Chloro-1H-indole-3-acetate	Generator
(4-Chloro-1H-indol-3-yl)acetic acid	HMDB
4-Chloro-iaa	HMDB
4-Chloroindole-3-acetate	HMDB
4-Chloroindole-3-acetic acid	HMDB
4-Chloro-1H-indole-3-acetic acid	ChEBI

Chemical Formula

C₁₀H₈ClNO₂

Average Mass

209.6290 Da

Monoisotopic Mass

209.02436 Da

IUPAC Name

2-(4-chloro-1H-indol-3-yl)acetic acid

Traditional Name

4-chloroindole-3-acetic acid

CAS Registry Number

2519-61-1

SMILES

OC(=O)CC1=CNC2=C1C(Cl)=CC=C2

InChI Identifier

InChI=1S/C10H8ClNO2/c11-7-2-1-3-8-10(7)6(5-12-8)4-9(13)14/h1-3,5,12H,4H2,(H,13,14)

InChI Key

WNCFBCKZRJDRKZ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lathyrus latifolius	Plant	KNApSAcK
Lathyrus maritimus	Plant	KNApSAcK
Lathyrus odoratus	Plant	KNApSAcK
Lathyrus sativus	FooDB	KNAPSACK
Lens culinaris	FooDB	KNAPSACK
Pinus sylvestris	Plant	KNApSAcK
Pisum sativum	FooDB	KNAPSACK
Vicia amurensis	Plant	KNApSAcK
Vicia faba	FooDB	KNAPSACK
Vicia sativa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indole-3-acetic acid derivatives

Alternative Parents

Substituents

Indole-3-acetic acid derivative
3-alkylindole
Indole
Aryl chloride
Aryl halide
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

chloroindole-3-acetic acid (CHEBI:20339 )

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	2.3	ALOGPS
logP	2.31	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	4.14	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	53.09 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	53.26 m³·mol⁻¹	ChemAxon
Polarizability	19.92 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0032936

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB010921

KNApSAcK ID

C00000102

Chemspider ID

90727

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100413

PDB ID

Not Available

ChEBI ID

20339

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4-Chloro-1H-indole-3-acetic acid (NP0047496)

MOL for NP0047496 (4-Chloro-1H-indole-3-acetic acid)

3D MOL for NP0047496 (4-Chloro-1H-indole-3-acetic acid)

3D SDF for NP0047496 (4-Chloro-1H-indole-3-acetic acid)

3D-SDF for NP0047496 (4-Chloro-1H-indole-3-acetic acid)

PDB for NP0047496 (4-Chloro-1H-indole-3-acetic acid)

3D PDB for NP0047496 (4-Chloro-1H-indole-3-acetic acid)

SMILES for NP0047496 (4-Chloro-1H-indole-3-acetic acid)

INCHI for NP0047496 (4-Chloro-1H-indole-3-acetic acid)

Structure for NP0047496 (4-Chloro-1H-indole-3-acetic acid)

3D Structure for NP0047496 (4-Chloro-1H-indole-3-acetic acid)