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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 20:17:14 UTC

Update Date

2021-09-26 23:15:39 UTC

HMDB ID

HMDB0258628

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1-Methyl-3-(2-oxopropylidene)indol-2-one

Description

1-methyl-3-(2-oxopropylidene)-2,3-dihydro-1H-indol-2-one belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Based on a literature review very few articles have been published on 1-methyl-3-(2-oxopropylidene)-2,3-dihydro-1H-indol-2-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). 1-methyl-3-(2-oxopropylidene)indol-2-one is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 1-Methyl-3-(2-oxopropylidene)indol-2-one is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652309112122172D          

 15 16  0  0  0  0            999 V2000
   -0.1781    1.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768    0.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752    0.3126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    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
    2.6378   -1.5229    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   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   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
  4  2  1  4  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  2  0  0  0  0
 12 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0258628

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C(=O)C(=CC(C)=O)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C12H11NO2/c1-8(14)7-10-9-5-3-4-6-11(9)13(2)12(10)15/h3-7H,1-2H3

> <INCHI_KEY>
CZKBLHCEDVWPRN-UHFFFAOYSA-N

> <FORMULA>
C12H11NO2

> <MOLECULAR_WEIGHT>
201.225

> <EXACT_MASS>
201.078978598

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
21.444356177262712

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-methyl-3-(2-oxopropylidene)-2,3-dihydro-1H-indol-2-one

> <ALOGPS_LOGP>
1.00

> <JCHEM_LOGP>
1.281921137

> <ALOGPS_LOGS>
-2.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.19348028309944

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4655069539144776

> <JCHEM_POLAR_SURFACE_AREA>
37.38

> <JCHEM_REFRACTIVITY>
57.94540000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-methyl-3-(2-oxopropylidene)indol-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -0.333   3.192   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.143   1.728   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.887   0.583   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.650   1.408   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       2.126  -2.549   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.320  -1.303   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12    5   14                                                  
CONECT   14   13                                                            
CONECT   15   12                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0258630
HETATM    1  C1  UNL     1       4.426  -0.537  -0.023  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.011  -0.982  -0.117  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.809  -2.176  -0.352  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.936  -0.052   0.060  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.650  -0.326   0.000  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.073  -1.540  -0.241  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.395  -2.668  -0.460  1.00  0.00           O  
HETATM    8  N1  UNL     1      -1.473  -1.226  -0.186  1.00  0.00           N  
HETATM    9  C6  UNL     1      -2.546  -2.150  -0.373  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.634   0.160   0.085  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.763   0.967   0.238  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.663   2.309   0.501  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.404   2.850   0.614  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.296   2.079   0.468  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.392   0.721   0.201  1.00  0.00           C  
HETATM   16  H1  UNL     1       5.084  -1.091  -0.720  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.772  -0.629   1.045  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.440   0.547  -0.256  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.242   1.004   0.269  1.00  0.00           H  
HETATM   20  H5  UNL     1      -3.369  -1.848   0.324  1.00  0.00           H  
HETATM   21  H6  UNL     1      -2.244  -3.174  -0.056  1.00  0.00           H  
HETATM   22  H7  UNL     1      -2.967  -2.119  -1.394  1.00  0.00           H  
HETATM   23  H8  UNL     1      -3.721   0.501   0.142  1.00  0.00           H  
HETATM   24  H9  UNL     1      -3.551   2.939   0.621  1.00  0.00           H  
HETATM   25  H10 UNL     1      -1.359   3.930   0.826  1.00  0.00           H  
HETATM   26  H11 UNL     1       0.689   2.512   0.557  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3    4
CONECT    4    5    5   19
CONECT    5    6   15
CONECT    6    7    7    8
CONECT    8    9   10
CONECT    9   20   21   22
CONECT   10   11   11   15
CONECT   11   12   23
CONECT   12   13   13   24
CONECT   13   14   25
CONECT   14   15   15   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Phenyl-2-propenal	MeSH
3-Phenylprop-2-enaldehyde	MeSH
trans-3-Phenylprop-2-enaldehyde	MeSH
beta-Phenylacrolein	MeSH
trans-Cinnamaldehyde	MeSH
Cinnamaldehyde	MeSH
Cinnamic aldehyde	MeSH
Cinnamic aldehyde, (e)-isomer	MeSH

Chemical Formula

C₁₂H₁₁NO₂

Average Molecular Weight

201.225

Monoisotopic Molecular Weight

201.078978598

IUPAC Name

1-methyl-3-(2-oxopropylidene)-2,3-dihydro-1H-indol-2-one

Traditional Name

1-methyl-3-(2-oxopropylidene)indol-2-one

CAS Registry Number

Not Available

SMILES

CN1C(=O)C(=CC(C)=O)C2=CC=CC=C12

InChI Identifier

InChI=1S/C12H11NO2/c1-8(14)7-10-9-5-3-4-6-11(9)13(2)12(10)15/h3-7H,1-2H3

InChI Key

CZKBLHCEDVWPRN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Not Available

Direct Parent

Indoles and derivatives

Alternative Parents

Substituents

Indole or derivatives
Benzenoid
Acryloyl-group
Enone
Tertiary carboxylic acid amide
Carboxamide group
Ketone
Lactam
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1	ALOGPS
logP	1.28	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	19.19	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	37.38 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	57.95 m³·mol⁻¹	ChemAxon
Polarizability	21.44 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	175.179	30932474
DeepCCS	[M+Na]+	149.737	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-Methyl-3-(2-oxopropylidene)indol-2-one,1TMS,isomer #1	C=C(C=C1C(=O)N(C)C2=CC=CC=C12)O[Si](C)(C)C	2027.7	Semi standard non polar	33892256
1-Methyl-3-(2-oxopropylidene)indol-2-one,1TMS,isomer #1	C=C(C=C1C(=O)N(C)C2=CC=CC=C12)O[Si](C)(C)C	1892.1	Standard non polar	33892256
1-Methyl-3-(2-oxopropylidene)indol-2-one,1TMS,isomer #1	C=C(C=C1C(=O)N(C)C2=CC=CC=C12)O[Si](C)(C)C	2488.2	Standard polar	33892256
1-Methyl-3-(2-oxopropylidene)indol-2-one,1TBDMS,isomer #1	C=C(C=C1C(=O)N(C)C2=CC=CC=C12)O[Si](C)(C)C(C)(C)C	2258.3	Semi standard non polar	33892256
1-Methyl-3-(2-oxopropylidene)indol-2-one,1TBDMS,isomer #1	C=C(C=C1C(=O)N(C)C2=CC=CC=C12)O[Si](C)(C)C(C)(C)C	2102.6	Standard non polar	33892256
1-Methyl-3-(2-oxopropylidene)indol-2-one,1TBDMS,isomer #1	C=C(C=C1C(=O)N(C)C2=CC=CC=C12)O[Si](C)(C)C(C)(C)C	2602.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methyl-3-(2-oxopropylidene)indol-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kg6-0910000000-2d2dcc4caa426aec5865	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methyl-3-(2-oxopropylidene)indol-2-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methyl-3-(2-oxopropylidene)indol-2-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methyl-3-(2-oxopropylidene)indol-2-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

26552853

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53421694

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 1-Methyl-3-(2-oxopropylidene)indol-2-one (HMDB0258628)

MOL for HMDB0258628 (1-Methyl-3-(2-oxopropylidene)indol-2-one)

3D MOL for HMDB0258628 (1-Methyl-3-(2-oxopropylidene)indol-2-one)

3D SDF for HMDB0258628 (1-Methyl-3-(2-oxopropylidene)indol-2-one)

3D-SDF for HMDB0258628 (1-Methyl-3-(2-oxopropylidene)indol-2-one)

PDB for HMDB0258628 (1-Methyl-3-(2-oxopropylidene)indol-2-one)

3D PDB for HMDB0258628 (1-Methyl-3-(2-oxopropylidene)indol-2-one)

SMILES for HMDB0258628 (1-Methyl-3-(2-oxopropylidene)indol-2-one)

INCHI for HMDB0258628 (1-Methyl-3-(2-oxopropylidene)indol-2-one)

Structure for HMDB0258628 (1-Methyl-3-(2-oxopropylidene)indol-2-one)

3D Structure for HMDB0258628 (1-Methyl-3-(2-oxopropylidene)indol-2-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra