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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:51:36 UTC

Update Date

2023-02-21 17:22:39 UTC

HMDB ID

HMDB0032757

Secondary Accession Numbers

HMDB32757

Metabolite Identification

Common Name

3-Methyl-9H-carbazole-9-carboxaldehyde

Description

3-Methyl-9H-carbazole-9-carboxaldehyde belongs to the class of organic compounds known as n-acylcarbazoles. These are aromatic heteropolycyclic compounds containing a carbazole moiety, which is N-acylated. 3-Methyl-9H-carbazole-9-carboxaldehyde has been detected, but not quantified in, herbs and spices. This could make 3-methyl-9H-carbazole-9-carboxaldehyde a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-Methyl-9H-carbazole-9-carboxaldehyde.

Structure

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


  Mrv0541 05061306402D          

 16 18  0  0  0  0            999 V2000
   -0.3896    1.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -1.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -0.6855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2195   -1.9230    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
  7  6  2  0  0  0  0
 10  1  1  0  0  0  0
 10  6  1  0  0  0  0
 10  8  2  0  0  0  0
 11  4  2  0  0  0  0
 12  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13  5  2  0  0  0  0
 13 11  1  0  0  0  0
 14  7  1  0  0  0  0
 14 12  2  0  0  0  0
 15  9  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16  9  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032757

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC2=C(C=C1)N(C=O)C1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C14H11NO/c1-10-6-7-14-12(8-10)11-4-2-3-5-13(11)15(14)9-16/h2-9H,1H3

> <INCHI_KEY>
ODQBPNZNDIOBFN-UHFFFAOYSA-N

> <FORMULA>
C14H11NO

> <MOLECULAR_WEIGHT>
209.2432

> <EXACT_MASS>
209.084063979

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
23.185190279173867

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-methyl-9H-carbazole-9-carbaldehyde

> <ALOGPS_LOGP>
3.16

> <JCHEM_LOGP>
2.87541748

> <ALOGPS_LOGS>
-3.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5924879151860076

> <JCHEM_POLAR_SURFACE_AREA>
22

> <JCHEM_REFRACTIVITY>
63.2932

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.77e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-methylcarbazole-9-carbaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -0.727   3.059   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.917   1.914   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.393   0.450   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.411   2.235   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.362  -0.695   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.173   0.450   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.858  -0.695   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.610  -2.820   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.380   1.090   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.856  -0.374   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       3.610  -1.280   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       2.276  -3.590   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2   11                                                       
CONECT    5    3   13                                                       
CONECT    6    7   10                                                       
CONECT    7    6   14                                                       
CONECT    8   10   12                                                       
CONECT    9   15   16                                                       
CONECT   10    1    6    8                                                  
CONECT   11    4   12   13                                                  
CONECT   12    8   11   14                                                  
CONECT   13    5   11   15                                                  
CONECT   14    7   12   15                                                  
CONECT   15    9   13   14                                                  
CONECT   16    9                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

COMPND    HMDB0032757
HETATM    1  C1  UNL     1      -3.905  -1.470   0.361  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.692  -0.603   0.227  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.787   0.771   0.164  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.672   1.593   0.040  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.412   1.018  -0.023  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.294  -0.356   0.039  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.423  -1.140   0.162  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.070  -0.596  -0.049  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.789  -1.778  -0.040  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.172  -1.787  -0.141  1.00  0.00           C  
HETATM   11  C11 UNL     1       3.858  -0.596  -0.253  1.00  0.00           C  
HETATM   12  C12 UNL     1       3.128   0.575  -0.259  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.747   0.599  -0.160  1.00  0.00           C  
HETATM   14  N1  UNL     1       0.827   1.581  -0.143  1.00  0.00           N  
HETATM   15  C14 UNL     1       1.121   2.965  -0.235  1.00  0.00           C  
HETATM   16  O1  UNL     1       0.235   3.856  -0.216  1.00  0.00           O  
HETATM   17  H1  UNL     1      -4.765  -0.820   0.583  1.00  0.00           H  
HETATM   18  H2  UNL     1      -4.109  -2.045  -0.554  1.00  0.00           H  
HETATM   19  H3  UNL     1      -3.769  -2.214   1.176  1.00  0.00           H  
HETATM   20  H4  UNL     1      -3.774   1.209   0.213  1.00  0.00           H  
HETATM   21  H5  UNL     1      -1.766   2.673  -0.009  1.00  0.00           H  
HETATM   22  H6  UNL     1      -1.280  -2.210   0.206  1.00  0.00           H  
HETATM   23  H7  UNL     1       1.257  -2.705   0.046  1.00  0.00           H  
HETATM   24  H8  UNL     1       3.700  -2.743  -0.131  1.00  0.00           H  
HETATM   25  H9  UNL     1       4.933  -0.609  -0.331  1.00  0.00           H  
HETATM   26  H10 UNL     1       3.668   1.525  -0.348  1.00  0.00           H  
HETATM   27  H11 UNL     1       2.140   3.306  -0.327  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    3    7
CONECT    3    4   20
CONECT    4    5    5   21
CONECT    5    6   14
CONECT    6    7    7    8
CONECT    7   22
CONECT    8    9    9   13
CONECT    9   10   23
CONECT   10   11   11   24
CONECT   11   12   25
CONECT   12   13   13   26
CONECT   13   14
CONECT   14   15
CONECT   15   16   16   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
9-Formyl-3-methyl-9H-carbazole	HMDB
9-Formyl-3-methylcarbazole	MeSH

Chemical Formula

C₁₄H₁₁NO

Average Molecular Weight

209.2432

Monoisotopic Molecular Weight

209.084063979

IUPAC Name

3-methyl-9H-carbazole-9-carbaldehyde

Traditional Name

3-methylcarbazole-9-carbaldehyde

CAS Registry Number

Not Available

SMILES

CC1=CC2=C(C=C1)N(C=O)C1=CC=CC=C21

InChI Identifier

InChI=1S/C14H11NO/c1-10-6-7-14-12(8-10)11-4-2-3-5-13(11)15(14)9-16/h2-9H,1H3

InChI Key

ODQBPNZNDIOBFN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acylcarbazoles. These are aromatic heteropolycyclic compounds containing a carbazole moiety, which is N-acylated.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

N-acylcarbazoles

Alternative Parents

Substituents

N-acylcarbazole
Indole
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0032757)
Cell membrane (HMDB: HMDB0032757)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032757)

Source

Exogenous

Food

Food (HMDB: HMDB0032757)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0032757)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0032757)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	58 - 60 °C	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
Water Solubility	0.028 g/L	ALOGPS
logP	3.16	ALOGPS
logP	2.88	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	22 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	63.29 m³·mol⁻¹	ChemAxon
Polarizability	23.19 Å³	ChemAxon
Number of Rings	3	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
DarkChem	[M+H]+	146.827	31661259
DarkChem	[M-H]-	146.33	31661259
DeepCCS	[M-2H]-	176.901	30932474
DeepCCS	[M+Na]+	151.977	30932474
AllCCS	[M+H]+	144.2	32859911
AllCCS	[M+H-H2O]+	139.9	32859911
AllCCS	[M+NH4]+	148.2	32859911
AllCCS	[M+Na]+	149.4	32859911
AllCCS	[M-H]-	148.2	32859911
AllCCS	[M+Na-2H]-	147.5	32859911
AllCCS	[M+HCOO]-	146.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Methyl-9H-carbazole-9-carboxaldehyde	CC1=CC2=C(C=C1)N(C=O)C1=CC=CC=C21	3318.5	Standard polar	33892256
3-Methyl-9H-carbazole-9-carboxaldehyde	CC1=CC2=C(C=C1)N(C=O)C1=CC=CC=C21	2084.9	Standard non polar	33892256
3-Methyl-9H-carbazole-9-carboxaldehyde	CC1=CC2=C(C=C1)N(C=O)C1=CC=CC=C21	2196.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-9H-carbazole-9-carboxaldehyde GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-1910000000-598179bcfd398558cae2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-9H-carbazole-9-carboxaldehyde GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-9H-carbazole-9-carboxaldehyde GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-9H-carbazole-9-carboxaldehyde 10V, Positive-QTOF	splash10-03di-0090000000-7821841eca565ede0553	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-9H-carbazole-9-carboxaldehyde 20V, Positive-QTOF	splash10-03di-0190000000-a863c4657a7dfd6dd5e3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-9H-carbazole-9-carboxaldehyde 40V, Positive-QTOF	splash10-001i-0900000000-eb8431894a560840c1f0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-9H-carbazole-9-carboxaldehyde 10V, Negative-QTOF	splash10-0a4i-0090000000-92df123f2a5034b0cc83	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-9H-carbazole-9-carboxaldehyde 20V, Negative-QTOF	splash10-0a4i-0090000000-e353e991f0b9c3e78dc1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-9H-carbazole-9-carboxaldehyde 40V, Negative-QTOF	splash10-0a6r-2890000000-f7eceb6f7d0fbc76fcc4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-9H-carbazole-9-carboxaldehyde 10V, Negative-QTOF	splash10-001i-0900000000-54974cb9283f7df5a203	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-9H-carbazole-9-carboxaldehyde 20V, Negative-QTOF	splash10-001i-0940000000-10a1c36837022951acf8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-9H-carbazole-9-carboxaldehyde 40V, Negative-QTOF	splash10-0a4i-0390000000-f4609dbe1e60e102694e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-9H-carbazole-9-carboxaldehyde 10V, Positive-QTOF	splash10-03e9-0490000000-8a9fe6c37d956ff4355f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-9H-carbazole-9-carboxaldehyde 20V, Positive-QTOF	splash10-001i-0920000000-d9066b22a87b8670da4b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-9H-carbazole-9-carboxaldehyde 40V, Positive-QTOF	splash10-001i-0900000000-d0219683bbe5f68d8356	2021-09-23	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB010724

KNApSAcK ID

Not Available

Chemspider ID

8234479

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10058925

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 3-Methyl-9H-carbazole-9-carboxaldehyde (HMDB0032757)

MOL for HMDB0032757 (3-Methyl-9H-carbazole-9-carboxaldehyde)

3D MOL for HMDB0032757 (3-Methyl-9H-carbazole-9-carboxaldehyde)

3D SDF for HMDB0032757 (3-Methyl-9H-carbazole-9-carboxaldehyde)

3D-SDF for HMDB0032757 (3-Methyl-9H-carbazole-9-carboxaldehyde)

PDB for HMDB0032757 (3-Methyl-9H-carbazole-9-carboxaldehyde)

3D PDB for HMDB0032757 (3-Methyl-9H-carbazole-9-carboxaldehyde)

SMILES for HMDB0032757 (3-Methyl-9H-carbazole-9-carboxaldehyde)

INCHI for HMDB0032757 (3-Methyl-9H-carbazole-9-carboxaldehyde)

Structure for HMDB0032757 (3-Methyl-9H-carbazole-9-carboxaldehyde)

3D Structure for HMDB0032757 (3-Methyl-9H-carbazole-9-carboxaldehyde)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra