NP-MRD: Showing NP-Card for Norharman (NP0021476)

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Record Information

Version

2.0

Created at

2021-01-06 06:45:35 UTC

Updated at

2021-08-20 00:00:00 UTC

NP-MRD ID

NP0021476

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Norharman

Provided By

NPAtlas

Description

Beta-Carboline, also known as norharman or 9H-b-carboline, belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. Beta-Carboline is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Norharman is found in Ailanthus altissima, Ailanthus triphysa, Anabaenopsis siamensis (Antarikanonda) Komarek & Anagnostidis, Brucea mollis, Commelina communis, Coriolus, Cribricellina cribraria, Datura metel , Tetradium glabrifolium, Eurycoma longifolia, Hannoa klaineana, Heliconius erato, Homo sapiens, Isatis tinctoria, Nicotiana tabacum, Noctiluca scintillans, Panax ginseng, Passiflora incarnata, Picrasma quassioides, Quassia africana, Rauvolfia serpentina, Rauvolfia sumatrana, Senecio leptolobus, Streptomyces nigra, Strychnos johnsonii, Strychnos potatorum, Synechocystis aquatilis, Tedania anhelans, Trametes maxima and Tribulus terrestris L. . Norharman was first documented in 2001 (PMID: 11374564). Based on a literature review very few articles have been published on beta-Carboline (PMID: 19255684).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105163D          

 21 23  0  0  0  0            999 V2000
   -3.2094   -0.1077   -0.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7268    1.1760   -0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3768    1.4093   -0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4518    0.3771   -0.0337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9530   -0.9063   -0.0203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3056   -1.1434   -0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1413   -1.7172    0.0582 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2663   -0.9948    0.0926 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5927   -1.2966    0.1675 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5490   -0.3240    0.1860 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2446    0.9838    0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9108    1.3148    0.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9223    0.3467    0.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2939   -0.3137   -0.2039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4154    1.9973   -0.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9500    2.4131   -0.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6592   -2.1844   -0.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0816   -2.7626    0.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9414   -2.3114    0.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0619    1.6884    0.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6300    2.3556    0.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  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
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  6  1  1  0  0  0  0
 13  8  1  0  0  0  0
 13  4  1  0  0  0  0
  1 14  1  0  0  0  0
  2 15  1  0  0  0  0
  3 16  1  0  0  0  0
  6 17  1  0  0  0  0
  7 18  1  0  0  0  0
  9 19  1  0  0  0  0
 11 20  1  0  0  0  0
 12 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021476

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N1C2=C([H])N=C([H])C([H])=C2C2=C([H])C([H])=C([H])C([H])=C12

> <INCHI_IDENTIFIER>
InChI=1S/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H

> <INCHI_KEY>
AIFRHYZBTHREPW-UHFFFAOYSA-N

> <FORMULA>
C11H8N2

> <MOLECULAR_WEIGHT>
168.1946

> <EXACT_MASS>
168.068748266

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
18.066186690991525

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9H-pyrido[3,4-b]indole

> <ALOGPS_LOGP>
2.56

> <JCHEM_LOGP>
1.8732132623333335

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.223870765973725

> <JCHEM_PKA_STRONGEST_BASIC>
5.284479184974655

> <JCHEM_POLAR_SURFACE_AREA>
28.68

> <JCHEM_REFRACTIVITY>
51.31530000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.87e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-carboline

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.209  -0.108  -0.156  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.727   1.176  -0.171  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.377   1.409  -0.110  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.452   0.377  -0.034  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.953  -0.906  -0.020  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.306  -1.143  -0.080  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.141  -1.717   0.058  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.266  -0.995   0.093  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.593  -1.297   0.168  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.549  -0.324   0.186  0.00  0.00           N+0
HETATM   11  C   UNK     0       3.245   0.984   0.132  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.911   1.315   0.056  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.922   0.347   0.036  0.00  0.00           C+0
HETATM   14  H   UNK     0      -4.294  -0.314  -0.204  0.00  0.00           H+0
HETATM   15  H   UNK     0      -3.415   1.997  -0.229  0.00  0.00           H+0
HETATM   16  H   UNK     0      -0.950   2.413  -0.119  0.00  0.00           H+0
HETATM   17  H   UNK     0      -2.659  -2.184  -0.067  0.00  0.00           H+0
HETATM   18  H   UNK     0       0.082  -2.763   0.087  0.00  0.00           H+0
HETATM   19  H   UNK     0       2.941  -2.311   0.215  0.00  0.00           H+0
HETATM   20  H   UNK     0       4.062   1.688   0.151  0.00  0.00           H+0
HETATM   21  H   UNK     0       1.630   2.356   0.011  0.00  0.00           H+0
CONECT    1    2    6   14                                                  
CONECT    2    1    3   15                                                  
CONECT    3    2    4   16                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1   17                                                  
CONECT    7    5    8   18                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13   21                                                  
CONECT   13   12    8    4                                                  
CONECT   14    1                                                            
CONECT   15    2                                                            
CONECT   16    3                                                            
CONECT   17    6                                                            
CONECT   18    7                                                            
CONECT   19    9                                                            
CONECT   20   11                                                            
CONECT   21   12                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
2,9-Diazafluorene	ChEBI
2-Azacarbazole	ChEBI
9H-beta-Carboline	ChEBI
9H-Pyrido(3,4-b)indole	ChEBI
9H-Pyrido[3,4-b]indole	ChEBI
Carbazoline	ChEBI
Norharman	ChEBI
Norharmane	ChEBI
9H-b-Carboline	Generator
9H-Β-carboline	Generator
b-Carboline	Generator
Β-carboline	Generator
Norharman hydrochloride	MeSH
Norhormane	MeSH
beta-Carboline	HMDB, MeSH

Chemical Formula

C₁₁H₈N₂

Average Mass

168.1946 Da

Monoisotopic Mass

168.06875 Da

IUPAC Name

9H-pyrido[3,4-b]indole

Traditional Name

β-carboline

CAS Registry Number

Not Available

SMILES

N1C2=CC=CC=C2C2=C1C=NC=C2

InChI Identifier

InChI=1S/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H

InChI Key

AIFRHYZBTHREPW-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ailanthus altissima	LOTUS Database	35616633
Ailanthus triphysus	LOTUS Database	35616633
Anabaena cylindrica Lemmermann	KNApSAcK Database	22123792
Anabaena inaequalis (Kuetzing)Bornet & Flahault	KNApSAcK Database	22123792
Anabaenopsis siamensis (Antarikanonda) Komarek & Anagnostidis	-	KNApSAcK
Brucea mollis	LOTUS Database	35616633
Cichorium intybus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Commelina communis	LOTUS Database	35616633
Coriolus	NPAtlas	4798774
Cribricellina cribraria	LOTUS Database	35616633
Datura metel	Plant	KNApSAcK
Euodia fargesii	LOTUS Database	35616633
Eurycoma longifolia	LOTUS Database	35616633
Festuca arundinacea Schreb.	KNApSAcK Database	22123792
Hannoa klaineana	LOTUS Database	35616633
Heliconius erato	LOTUS Database	35616633
Homo sapiens	LOTUS Database	35616633
Isatis tinctoria	LOTUS Database	35616633
Lolium perenne L.	KNApSAcK Database	22123792
Nicotiana tabacum	LOTUS Database	35616633
Noctiluca scintillans	LOTUS Database	35616633
Panax ginseng	LOTUS Database	35616633
Passiflora incarnata	LOTUS Database	35616633
Passiflora incarnata L.	KNApSAcK Database	22123792
Picrasma quassioides	LOTUS Database	35616633
Pinellia pedatisecta	KNApSAcK Database	22123792
Polygala tenuifolia	KNApSAcK Database	22123792
Psychotria viridis	KNApSAcK Database	22123792
Quassia africana	LOTUS Database	35616633
Rauvolfia serpentina	LOTUS Database	35616633
Rauvolfia sumatrana	LOTUS Database	35616633
Senecio leptolobus	LOTUS Database	35616633
Streptomyces nigra	LOTUS Database	35616633
Strychnos barnhartiana Krukoff.	KNApSAcK Database	22123792
Strychnos johnsonii	LOTUS Database	35616633
Strychnos potatorum	LOTUS Database	35616633
Synechocystis aquatilis	LOTUS Database	35616633
Tedania anhelans	-	KNApSAcK
Trametes maxima	LOTUS Database	35616633
Tribulus terrestris	Plant	KNApSAcK
Tribulus terrestris L.	KNApSAcK Database	22123792

Species Where Detected

Species Name	Source	Reference
Nodularia harveyana Thuret ex Bornet et Flahault	KNApSAcK Database	22123792
Nostoc carneum C. Agardh ex Bornet & Flahault	KNApSAcK Database	22123792
Nostoc commune Vaucher ex Bornet & Flahault	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyridoindoles

Direct Parent

Beta carbolines

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	199.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	391.30 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	9.55 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.170	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	2.56	ALOGPS
logP	1.87	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	13.22	ChemAxon
pKa (Strongest Basic)	5.28	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	28.68 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	51.32 m³·mol⁻¹	ChemAxon
Polarizability	18.07 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

External Links

NPAtlas ID

NPA007873

HMDB ID

HMDB0012897

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Beta-Carboline

METLIN ID

Not Available

PubChem Compound

PDB ID

ChEBI ID

Good Scents ID

References

General References

Hidalgo J, Sanchez-Coronilla A, Balon M, Asuncion Munoz M, Carmona C: Dual emission of temperature-induced betacarboline self-associated hydrogen bond aggregates. Photochem Photobiol Sci. 2009 Mar;8(3):414-20. doi: 10.1039/b816776a. Epub 2009 Jan 20. [PubMed:19255684 ]
Munoz MA, Sama O, Galan M, Guardado P, Carmona C, Balon M: Hydrogen bonding NH/pi interactions between betacarboline and methyl benzene derivatives. Spectrochim Acta A Mol Biomol Spectrosc. 2001 Apr;57A(5):1049-56. doi: 10.1016/s1386-1425(00)00421-2. [PubMed:11374564 ]

Showing NP-Card for Norharman (NP0021476)

MOL for NP0021476 (Norharman)

3D MOL for NP0021476 (Norharman)

3D SDF for NP0021476 (Norharman)

3D-SDF for NP0021476 (Norharman)

PDB for NP0021476 (Norharman)

3D PDB for NP0021476 (Norharman)

SMILES for NP0021476 (Norharman)

INCHI for NP0021476 (Norharman)

Structure for NP0021476 (Norharman)

3D Structure for NP0021476 (Norharman)