Cannabis Compound Database: Showing Compound Card for Carbazole (CDB005370)

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Record Information

Version

1.0

Created at

2020-04-27 16:13:50 UTC

Updated at

2021-01-04 20:40:19 UTC

CannabisDB ID

CDB005370

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Carbazole

Description

Carbazole, also known as 9H-Carbazole, 9-azafluorene or dibenzopyrrole, 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. The compound has an indole structure, but where the second benzene ring is fused at the 2‚ 3 position of the indole five-membered ring (equivalent to the 9a‚ 4a double bond in carbazole, respectively). 9H-Carbazole is a weakly acidic compound and is potentially toxic. Carbazole alkaloids exhibit anti-oxidant, anti-viral, neuroprotective, anti-tumour activities and are used in anticancer drugs (PMID: 28966267 ; PMID: 31109016 ; PMID: 31328585 ). Carbazole is a constituent of tobacco smoke (PMID: 21556207 ). Carbazole is also formed during the combustion of cannabis and, as such, is a constituent of cannabis smoke ( Ref:DOI ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
9-Azafluorene	ChEBI
Dibenzo[b,D]pyrrole	ChEBI
Dibenzopyrrole	ChEBI
Diphenylenimide	ChEBI
Diphenylenimine	ChEBI
9H-Carbazole	Kegg
Dibenzo(b,D)pyrrole	MeSH
Carbazole	ChEBI

Chemical Formula

C₁₂H₉N

Average Molecular Weight

167.21

Monoisotopic Molecular Weight

167.0735

IUPAC Name

9H-carbazole

Traditional Name

carbazole

CAS Registry Number

86-74-8

SMILES

N1C2=CC=CC=C2C2=CC=CC=C12

InChI Identifier

InChI=1S/C12H9N/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8,13H

InChI Key

UJOBWOGCFQCDNV-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
Benzenoid
Heteroaromatic compound
Pyrrole
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

carbazole (CHEBI:27543 )
a carbazole (CPD-12475 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	246.3 °C	Wikipedia
Boiling Point	354.69 °C	Wikipedia
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.69	ALOGPS
logP	3.09	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	14.97	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	15.79 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	53.47 m³·mol⁻¹	ChemAxon
Polarizability	18.82 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

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Carbazole, non-derivatized, GC-MS Spectrum	splash10-014i-2900000000-b78b8a115b67c322c356	Spectrum
GC-MS	Carbazole, non-derivatized, GC-MS Spectrum	splash10-014i-1900000000-f38f5086059cb3ac8982	Spectrum
Predicted GC-MS	Carbazole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014i-0900000000-6b8ed13c96547bc917c2	Spectrum
Predicted GC-MS	Carbazole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-8d3916df8fb5bf7cb497	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-bb2897ade782d2cb28a3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-2e0ee0ac796cf07f5e08	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-570e0710549621003367	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-09a94e4635c7ccd85513	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udi-1900000000-8bc19b11f61d9a4a2b7b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0f79-6900000000-a67fbf7a4377e88ed6ec	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0674-9600000000-b9e5f8f30eba4f410838	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00kf-9400000000-997f1b12553eb140d577	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-016u-9500000000-439210ff3228097f7d4d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-014i-0900000000-31a551a3b0c039b14e7c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - APCI-ITFT , positive	splash10-014i-0900000000-87189b4441e2b819dbc3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-014i-0900000000-31a551a3b0c039b14e7c	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-05739bb49ad3bad95f93	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-2f7c32756cfcba4a70f1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0900000000-2291e1777d6832ba096b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-0ccc45575abcdef01c11	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-0ccc45575abcdef01c11	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0900000000-9d332fa2fa316b0417d3	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-2e4482a79bf9fdbdf05d	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-2e4482a79bf9fdbdf05d	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0900000000-f496b9f5cf5ef7445899	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-de30817c2d52bd6bbcb7	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-de30817c2d52bd6bbcb7	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0900000000-de30817c2d52bd6bbcb7	2021-10-12	View Spectrum

NMR

Not Available

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0249614

DrugBank ID

DB07301

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Carbazole

METLIN ID

Not Available

PubChem Compound

6854

PDB ID

Not Available

ChEBI ID

27543

References

General References

Hieda Y: Total Syntheses of Multi-substituted Carbazole Alkaloids and Phenolic Related Compounds, and Evaluation of Their Antioxidant Activities. Yakugaku Zasshi. 2017;137(10):1255-1263. doi: 10.1248/yakushi.17-00142. [PubMed:28966267 ]
Caruso A, Ceramella J, Iacopetta D, Saturnino C, Mauro MV, Bruno R, Aquaro S, Sinicropi MS: Carbazole Derivatives as Antiviral Agents: An Overview. Molecules. 2019 May 17;24(10). pii: molecules24101912. doi: 10.3390/molecules24101912. [PubMed:31109016 ]
Issa S, Prandina A, Bedel N, Rongved P, Yous S, Le Borgne M, Bouaziz Z: Carbazole scaffolds in cancer therapy: a review from 2012 to 2018. J Enzyme Inhib Med Chem. 2019 Dec;34(1):1321-1346. doi: 10.1080/14756366.2019.1640692. [PubMed:31328585 ]
Talhout R, Schulz T, Florek E, van Benthem J, Wester P, Opperhuizen A: Hazardous compounds in tobacco smoke. Int J Environ Res Public Health. 2011 Feb;8(2):613-28. doi: 10.3390/ijerph8020613. Epub 2011 Feb 23. [PubMed:21556207 ]

Showing Compound Card for Carbazole (CDB005370)

Structure for CDB005370 (Carbazole)