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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:07:52 UTC

Update Date

2022-03-07 02:57:01 UTC

HMDB ID

HMDB0041443

Secondary Accession Numbers

HMDB41443

Metabolite Identification

Common Name

Mukolidine

Description

Mukolidine belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring. Mukolidine has been detected, but not quantified in, herbs and spices. This could make mukolidine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Mukolidine.

Structure

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


  Mrv0541 05061312402D          

 17 19  0  0  0  0            999 V2000
    1.7172    2.9069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4820    0.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2890    0.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2271    1.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2800    1.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7279    1.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2180    0.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5771   -0.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0250    0.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8410    0.9946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6660    0.9946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9210    1.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7791    1.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5861    1.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2535    2.2642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3840    0.1115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5242    2.7354    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
  6  5  2  0  0  0  0
  9  5  1  0  0  0  0
  9  7  2  0  0  0  0
  9  8  1  0  0  0  0
 10  3  1  0  0  0  0
 11  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12  6  1  0  0  0  0
 12 11  2  0  0  0  0
 13  4  2  0  0  0  0
 14 10  2  0  0  0  0
 14 13  1  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16  8  2  0  0  0  0
 17  1  1  0  0  0  0
 17 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041443

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=CC2=C1NC1=C2C=C(C=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H11NO2/c1-17-13-4-2-3-10-11-7-9(8-16)5-6-12(11)15-14(10)13/h2-8,15H,1H3

> <INCHI_KEY>
KSTPFEFAPRYLOZ-UHFFFAOYSA-N

> <FORMULA>
C14H11NO2

> <MOLECULAR_WEIGHT>
225.2426

> <EXACT_MASS>
225.078978601

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
24.128797927244694

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-methoxy-9H-carbazole-3-carbaldehyde

> <ALOGPS_LOGP>
3.13

> <JCHEM_LOGP>
2.645716768333333

> <ALOGPS_LOGS>
-4.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.43582852693062

> <JCHEM_PKA_STRONGEST_BASIC>
-4.886153623856048

> <JCHEM_POLAR_SURFACE_AREA>
42.09

> <JCHEM_REFRACTIVITY>
66.51939999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-methoxy-9H-carbazole-3-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

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       3.205   5.426   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.633   1.032   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.139   0.712   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.157   2.497   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.723   2.497   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.692   3.641   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.740   0.712   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.277  -0.112   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.247   1.032   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.170   1.857   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.710   1.857   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.186   3.321   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.188   3.641   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.694   3.321   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       7.940   4.227   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0      13.783   0.208   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.712   5.106   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2    3    4                                                       
CONECT    3    2   10                                                       
CONECT    4    2   13                                                       
CONECT    5    6    9                                                       
CONECT    6    5   12                                                       
CONECT    7    9   11                                                       
CONECT    8    9   16                                                       
CONECT    9    5    7    8                                                  
CONECT   10    3   11   14                                                  
CONECT   11    7   10   12                                                  
CONECT   12    6   11   15                                                  
CONECT   13    4   14   17                                                  
CONECT   14   10   13   15                                                  
CONECT   15   12   14                                                       
CONECT   16    8                                                            
CONECT   17    1   13                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0041443
HETATM    1  C1  UNL     1      -4.651   0.891   0.467  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.276   0.958   0.643  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.341   0.194  -0.013  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.769  -0.731  -0.935  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.873  -1.535  -1.632  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.519  -1.417  -1.409  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.076  -0.505  -0.498  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.987   0.299   0.198  1.00  0.00           C  
HETATM    9  N1  UNL     1      -0.275   1.080   1.005  1.00  0.00           N  
HETATM   10  C8  UNL     1       1.055   0.808   0.853  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.172   1.334   1.447  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.410   0.856   1.090  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.554  -0.151   0.136  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.861  -0.652  -0.237  1.00  0.00           C  
HETATM   15  O2  UNL     1       5.889  -0.183   0.296  1.00  0.00           O  
HETATM   16  C13 UNL     1       2.438  -0.679  -0.461  1.00  0.00           C  
HETATM   17  C14 UNL     1       1.202  -0.188  -0.090  1.00  0.00           C  
HETATM   18  H1  UNL     1      -5.148   1.398   1.332  1.00  0.00           H  
HETATM   19  H2  UNL     1      -4.947  -0.196   0.530  1.00  0.00           H  
HETATM   20  H3  UNL     1      -5.029   1.336  -0.457  1.00  0.00           H  
HETATM   21  H4  UNL     1      -3.816  -0.894  -1.176  1.00  0.00           H  
HETATM   22  H5  UNL     1      -2.205  -2.261  -2.354  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.188  -2.039  -1.947  1.00  0.00           H  
HETATM   24  H7  UNL     1      -0.670   1.788   1.651  1.00  0.00           H  
HETATM   25  H8  UNL     1       2.024   2.119   2.188  1.00  0.00           H  
HETATM   26  H9  UNL     1       4.286   1.271   1.559  1.00  0.00           H  
HETATM   27  H10 UNL     1       4.957  -1.428  -0.973  1.00  0.00           H  
HETATM   28  H11 UNL     1       2.546  -1.473  -1.212  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   21
CONECT    5    6    6   22
CONECT    6    7   23
CONECT    7    8    8   17
CONECT    8    9
CONECT    9   10   24
CONECT   10   11   11   17
CONECT   11   12   25
CONECT   12   13   13   26
CONECT   13   14   16
CONECT   14   15   15   27
CONECT   16   17   17   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Formyl-8-methoxycarbazole	HMDB
6-Formyl-1-methoxycarbazole	HMDB
8-Methoxy-9H-carbazole-3-carboxaldehyde, 9ci	HMDB

Chemical Formula

C₁₄H₁₁NO₂

Average Molecular Weight

225.2426

Monoisotopic Molecular Weight

225.078978601

IUPAC Name

8-methoxy-9H-carbazole-3-carbaldehyde

Traditional Name

8-methoxy-9H-carbazole-3-carbaldehyde

CAS Registry Number

87264-45-7

SMILES

COC1=CC=CC2=C1NC1=C2C=C(C=O)C=C1

InChI Identifier

InChI=1S/C14H11NO2/c1-17-13-4-2-3-10-11-7-9(8-16)5-6-12(11)15-14(10)13/h2-8,15H,1H3

InChI Key

KSTPFEFAPRYLOZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Carbazoles

Alternative Parents

Substituents

Carbazole
Indole
Anisole
Alkyl aryl ether
Aryl-aldehyde
Benzenoid
Pyrrole
Heteroaromatic compound
Ether
Azacycle
Hydrocarbon derivative
Aldehyde
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen 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: HMDB0041443)

Membrane (HMDB: HMDB0041443)
Cell membrane (HMDB: HMDB0041443)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041443)

Source

Exogenous

Food

Food (HMDB: HMDB0041443)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0041443)

Not Available

Nutrient (HMDB: HMDB0041443)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	152 - 155 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	6.49 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.023 g/L	ALOGPS
logP	3.13	ALOGPS
logP	2.65	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	13.44	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	42.09 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	66.52 m³·mol⁻¹	ChemAxon
Polarizability	24.13 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	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	151.224	31661259
DarkChem	[M-H]-	151.953	31661259
DeepCCS	[M+H]+	152.784	30932474
DeepCCS	[M-H]-	150.389	30932474
DeepCCS	[M-2H]-	183.273	30932474
DeepCCS	[M+Na]+	158.807	30932474
AllCCS	[M+H]+	150.0	32859911
AllCCS	[M+H-H2O]+	145.9	32859911
AllCCS	[M+NH4]+	153.9	32859911
AllCCS	[M+Na]+	155.0	32859911
AllCCS	[M-H]-	153.9	32859911
AllCCS	[M+Na-2H]-	153.3	32859911
AllCCS	[M+HCOO]-	152.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mukolidine	COC1=CC=CC2=C1NC1=C2C=C(C=O)C=C1	3293.5	Standard polar	33892256
Mukolidine	COC1=CC=CC2=C1NC1=C2C=C(C=O)C=C1	2379.6	Standard non polar	33892256
Mukolidine	COC1=CC=CC2=C1NC1=C2C=C(C=O)C=C1	2523.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Mukolidine,1TMS,isomer #1	COC1=CC=CC2=C1N([Si](C)(C)C)C1=CC=C(C=O)C=C21	2520.3	Semi standard non polar	33892256
Mukolidine,1TMS,isomer #1	COC1=CC=CC2=C1N([Si](C)(C)C)C1=CC=C(C=O)C=C21	2418.5	Standard non polar	33892256
Mukolidine,1TBDMS,isomer #1	COC1=CC=CC2=C1N([Si](C)(C)C(C)(C)C)C1=CC=C(C=O)C=C21	2689.2	Semi standard non polar	33892256
Mukolidine,1TBDMS,isomer #1	COC1=CC=CC2=C1N([Si](C)(C)C(C)(C)C)C1=CC=C(C=O)C=C21	2629.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Mukolidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00pj-0920000000-d2d25f7cd893c0d3b7fd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mukolidine 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 - Mukolidine 10V, Positive-QTOF	splash10-004i-0190000000-987befb17c20efddd48f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mukolidine 20V, Positive-QTOF	splash10-004i-0690000000-8f1ca6e6f30cc927c779	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mukolidine 40V, Positive-QTOF	splash10-00kf-0910000000-7fe6d09285e0d1ea6adc	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mukolidine 10V, Negative-QTOF	splash10-00di-0090000000-f352ca715f3724edda12	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mukolidine 20V, Negative-QTOF	splash10-00di-0190000000-fc5c02dbe538ab8c3fbc	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mukolidine 40V, Negative-QTOF	splash10-0a4i-0980000000-447fa16cefa56443b6e5	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mukolidine 10V, Positive-QTOF	splash10-004i-0090000000-86395f6d1953bbb88d81	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mukolidine 20V, Positive-QTOF	splash10-004i-0090000000-06652b247d0526c47c02	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mukolidine 40V, Positive-QTOF	splash10-008d-0930000000-fbccc42e31a2d12baa7f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mukolidine 10V, Negative-QTOF	splash10-00di-0090000000-9de6398b2721f078678f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mukolidine 20V, Negative-QTOF	splash10-001i-0910000000-9952055373c774cbb69c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mukolidine 40V, Negative-QTOF	splash10-00ec-0950000000-bc091f52c7a28ddcb7f9	2021-09-24	Wishart 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

FDB021394

KNApSAcK ID

C00024716

Chemspider ID

30777570

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53465568

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1892511

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 Mukolidine (HMDB0041443)

MOL for HMDB0041443 (Mukolidine)

3D MOL for HMDB0041443 (Mukolidine)

3D SDF for HMDB0041443 (Mukolidine)

3D-SDF for HMDB0041443 (Mukolidine)

PDB for HMDB0041443 (Mukolidine)

3D PDB for HMDB0041443 (Mukolidine)

SMILES for HMDB0041443 (Mukolidine)

INCHI for HMDB0041443 (Mukolidine)

Structure for HMDB0041443 (Mukolidine)

3D Structure for HMDB0041443 (Mukolidine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra