MiMeDB: Showing metabocard for N-{1-[4-(acetylamino)phenyl]-3-hydroxy-1-(1H-indol-3-yl)propan-2-yl}-2,2-dichloroacetamide (MMDBc0008650)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 01:25:53 UTC

Update Date

2022-08-31 06:28:55 UTC

Metabolite ID

MMDBc0008650

Metabolite Identification

Common Name

N-{1-[4-(acetylamino)phenyl]-3-hydroxy-1-(1H-indol-3-yl)propan-2-yl}-2,2-dichloroacetamide

Description

SCHEMBL17866799, also known as aphipd CPD, belongs to the class of organic compounds known as acetanilides. These are organic compounds containing an acetamide group conjugated to a phenyl group. Based on a literature review very few articles have been published on SCHEMBL17866799.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152103252D          

 29 31  0  0  0  0            999 V2000
    4.4509   -2.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809   -1.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2428   -0.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329   -1.9399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7948   -0.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -0.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8989   -2.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5399   -1.7684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -0.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8342    0.9540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822    0.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6412    0.7825    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.5793    1.7386    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0919   -2.3815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752    0.5124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -1.0568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1538   -1.4253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371   -0.4437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 12  1  1  0  0  0  0
 13  6  2  0  0  0  0
 13  7  1  0  0  0  0
 14  8  2  0  0  0  0
 14  9  1  0  0  0  0
 15  4  2  0  0  0  0
 16 10  2  0  0  0  0
 16 15  1  0  0  0  0
 17  5  2  0  0  0  0
 17 15  1  0  0  0  0
 18 11  1  0  0  0  0
 19 13  1  0  0  0  0
 19 16  1  0  0  0  0
 19 18  1  0  0  0  0
 21 20  1  0  0  0  0
 22 20  1  0  0  0  0
 23 20  1  0  0  0  0
 24 10  1  0  0  0  0
 24 17  1  0  0  0  0
 25 12  2  0  0  0  0
 25 14  1  4  0  0  0
 26 18  1  4  0  0  0
 26 21  2  0  0  0  0
 27 11  1  0  0  0  0
 28 12  1  0  0  0  0
 29 21  1  0  0  0  0
M  END


  Mrv1652305152103252D          

 29 31  0  0  0  0            999 V2000
    4.4509   -2.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809   -1.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2428   -0.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329   -1.9399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7948   -0.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -0.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8989   -2.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5399   -1.7684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -0.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8342    0.9540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822    0.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6412    0.7825    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.5793    1.7386    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0919   -2.3815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752    0.5124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -1.0568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1538   -1.4253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371   -0.4437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 12  1  1  0  0  0  0
 13  6  2  0  0  0  0
 13  7  1  0  0  0  0
 14  8  2  0  0  0  0
 14  9  1  0  0  0  0
 15  4  2  0  0  0  0
 16 10  2  0  0  0  0
 16 15  1  0  0  0  0
 17  5  2  0  0  0  0
 17 15  1  0  0  0  0
 18 11  1  0  0  0  0
 19 13  1  0  0  0  0
 19 16  1  0  0  0  0
 19 18  1  0  0  0  0
 21 20  1  0  0  0  0
 22 20  1  0  0  0  0
 23 20  1  0  0  0  0
 24 10  1  0  0  0  0
 24 17  1  0  0  0  0
 25 12  2  0  0  0  0
 25 14  1  4  0  0  0
 26 18  1  4  0  0  0
 26 21  2  0  0  0  0
 27 11  1  0  0  0  0
 28 12  1  0  0  0  0
 29 21  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0008650

> <DATABASE_NAME>
MIME

> <SMILES>
CC(O)=NC1=CC=C(C=C1)C(C(CO)N=C(O)C(Cl)Cl)C1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C21H21Cl2N3O3/c1-12(28)25-14-8-6-13(7-9-14)19(18(11-27)26-21(29)20(22)23)16-10-24-17-5-3-2-4-15(16)17/h2-10,18-20,24,27H,11H2,1H3,(H,25,28)(H,26,29)

> <INCHI_KEY>
IEORQMXIWXLRSB-UHFFFAOYSA-N

> <FORMULA>
C21H21Cl2N3O3

> <MOLECULAR_WEIGHT>
434.32

> <EXACT_MASS>
433.0959969

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
43.61685791856894

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,2-dichloro-N-(3-hydroxy-1-{4-[(1-hydroxyethylidene)amino]phenyl}-1-(1H-indol-3-yl)propan-2-yl)ethanimidic acid

> <ALOGPS_LOGP>
3.75

> <JCHEM_LOGP>
3.3451651878624022

> <ALOGPS_LOGS>
-5.12

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
5.696140023555773

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3084641635804464

> <JCHEM_PKA_STRONGEST_BASIC>
1.3818341128143832

> <JCHEM_POLAR_SURFACE_AREA>
101.2

> <JCHEM_REFRACTIVITY>
116.46140000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.29e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,2-dichloro-N-(3-hydroxy-1-{4-[(1-hydroxyethylidene)amino]phenyl}-1-(1H-indol-3-yl)propan-2-yl)ethanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0       8.308  -5.270   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.204  -2.477   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.187  -0.692   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.235  -3.621   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.217  -1.836   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.333  -1.652   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.278  -4.125   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.680  -1.012   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.741  -3.301   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.143  -0.188   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.424   1.781   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.393   0.636   0.000  0.00  0.00           C+0
HETATM   22 Cl   UNK     0      -4.930   1.461   0.000  0.00  0.00          Cl+0
HETATM   23 Cl   UNK     0      -2.948   3.245   0.000  0.00  0.00          Cl+0
HETATM   24  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0       5.772  -4.445   0.000  0.00  0.00           N+0
HETATM   26  N   UNK     0      -0.887   0.957   0.000  0.00  0.00           N+0
HETATM   27  O   UNK     0      -1.839  -1.973   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       7.754  -2.661   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -2.869  -0.828   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2   15                                                       
CONECT    5    3   17                                                       
CONECT    6    8   13                                                       
CONECT    7    9   13                                                       
CONECT    8    6   14                                                       
CONECT    9    7   14                                                       
CONECT   10   16   24                                                       
CONECT   11   18   27                                                       
CONECT   12    1   25   28                                                  
CONECT   13    6    7   19                                                  
CONECT   14    8    9   25                                                  
CONECT   15    4   16   17                                                  
CONECT   16   10   15   19                                                  
CONECT   17    5   15   24                                                  
CONECT   18   11   19   26                                                  
CONECT   19   13   16   18                                                  
CONECT   20   21   22   23                                                  
CONECT   21   20   26   29                                                  
CONECT   22   20                                                            
CONECT   23   20                                                            
CONECT   24   10   17                                                       
CONECT   25   12   14                                                       
CONECT   26   18   21                                                       
CONECT   27   11                                                            
CONECT   28   12                                                            
CONECT   29   21                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

Synonyms

Value	Source
APHIPD CPD	MeSH
N-(1-(4-(Acetylamino)phenyl)-3-hydroxy-1-(1H-indol-3-yl)propan-2-yl)-2,2-dichloroacetamide	MeSH

Molecular Formula

C₂₁H₂₁Cl₂N₃O₃

Average Mass

434.32

Monoisotopic Mass

433.0959969

IUPAC Name

2,2-dichloro-N-(3-hydroxy-1-{4-[(1-hydroxyethylidene)amino]phenyl}-1-(1H-indol-3-yl)propan-2-yl)ethanimidic acid

Traditional Name

2,2-dichloro-N-(3-hydroxy-1-{4-[(1-hydroxyethylidene)amino]phenyl}-1-(1H-indol-3-yl)propan-2-yl)ethanimidic acid

CAS Registry Number

Not Available

SMILES

CC(O)=NC1=CC=C(C=C1)C(C(CO)N=C(O)C(Cl)Cl)C1=CNC2=CC=CC=C12

InChI Identifier

InChI=1S/C21H21Cl2N3O3/c1-12(28)25-14-8-6-13(7-9-14)19(18(11-27)26-21(29)20(22)23)16-10-24-17-5-3-2-4-15(16)17/h2-10,18-20,24,27H,11H2,1H3,(H,25,28)(H,26,29)

InChI Key

IEORQMXIWXLRSB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acetanilides. These are organic compounds containing an acetamide group conjugated to a phenyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Anilides

Direct Parent

Acetanilides

Alternative Parents

Substituents

Acetanilide
3-alkylindole
Indole
N-acetylarylamine
Indole or derivatives
N-arylamide
Substituted pyrrole
Pyrrole
Heteroaromatic compound
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxide
Organopnictogen compound
Alcohol
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Alkyl chloride
Alkyl halide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0033 g/L	ALOGPS
logP	3.75	ALOGPS
logP	3.35	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	3.31	ChemAxon
pKa (Strongest Basic)	1.38	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	101.2 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	116.46 m³·mol⁻¹	ChemAxon
Polarizability	43.62 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78434810

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53350156

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for N-{1-[4-(acetylamino)phenyl]-3-hydroxy-1-(1H-indol-3-yl)propan-2-yl}-2,2-dichloroacetamide (MMDBc0008650)

MOL for #<Metabolite:0x00007f92509c0b78>

3D MOL for #<Metabolite:0x00007f92509c0b78>

3D SDF for #<Metabolite:0x00007f92509c0b78>

3D-SDF for #<Metabolite:0x00007f92509c0b78>

PDB for #<Metabolite:0x00007f92509c0b78>

3D PDB for #<Metabolite:0x00007f92509c0b78>

SMILES for #<Metabolite:0x00007f92509c0b78>

INCHI for #<Metabolite:0x00007f92509c0b78>

Structure for #<Metabolite:0x00007f92509c0b78>

3D Structure for #<Metabolite:0x00007f92509c0b78>