NP-MRD: Showing NP-Card for Brevicolline (NP0050840)

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Record Information

Version

2.0

Created at

2022-04-27 22:14:43 UTC

Updated at

2022-04-27 22:14:44 UTC

NP-MRD ID

NP0050840

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Brevicolline

Description

Brevicolline belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole. Brevicolline is found in Carex brevicollis . Brevicolline was first documented in 2006 (PMID: 16869657). Based on a literature review very few articles have been published on Brevicolline (PMID: 20890795).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 42  0  0  0  0  0  0  0  0999 V2000
   -3.3212   -2.7673    1.4704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0730   -2.1453    0.9411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9054   -2.7800    0.8987 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2229   -2.1907    0.4097 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2179   -0.8978   -0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4450   -0.3473   -0.5445 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6000   -1.3087   -0.7101 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3652   -1.2411    0.5766 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8616   -0.0026    1.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1062    0.6762    0.1683 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0999    1.3362   -0.6583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9808   -0.2195   -0.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1388   -0.8312    0.4662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1649    0.0239    0.3851 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7157    1.1618   -0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3450    2.3667   -0.4656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6484    3.4091   -1.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2934    3.2500   -1.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6480    2.0583   -0.9876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3554    1.0528   -0.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1190   -3.8648    1.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1535   -2.5905    0.7657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5510   -2.4271    2.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0783   -2.8584    0.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2663    0.0140   -1.6066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2671   -0.9571   -1.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3375   -2.3484   -0.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1219   -2.1157    1.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4744   -1.1856    0.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7447    0.5988    1.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1588   -0.2380    2.0373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9799    2.4433   -0.6387 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0341    1.0515   -1.7229 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1338    1.1226   -0.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1438   -0.1627    0.6870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3993    2.4625   -0.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1816    4.3320   -1.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7558    4.0820   -1.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3784    2.0377   -1.2311 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 13  1  0
 13 12  2  0
 12 20  1  0
 20 15  2  0
 15 14  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  6 10  1  0
 12  5  1  0
 19 20  1  0
 14 13  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
  9 30  1  0
  9 31  1  0
  8 28  1  0
  8 29  1  0
  7 26  1  0
  7 27  1  0
  6 25  1  6
  4 24  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
M  END


  Mrv1652304282200142D          

 20 23  0  0  1  0            999 V2000
    2.8985    1.1971    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
    3.4084   -0.3721    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
    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
    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
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 N   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
    0.9694    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2243    1.9817    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7394    2.6492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2243    3.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0090    3.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0090    2.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0856    2.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2046   -1.1567    0.0000 C   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
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  8 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
  7 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 15 19  1  0  0  0  0
 10 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050840

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CCC[C@H]1C1=CN=C(C)C2=C1C1=C(N2)C=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H19N3/c1-11-17-16(12-6-3-4-7-14(12)19-17)13(10-18-11)15-8-5-9-20(15)2/h3-4,6-7,10,15,19H,5,8-9H2,1-2H3/t15-/m0/s1

> <INCHI_KEY>
DIZAFWUMCZPYGF-HNNXBMFYSA-N

> <FORMULA>
C17H19N3

> <MOLECULAR_WEIGHT>
265.36

> <EXACT_MASS>
265.157897624

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
30.744848711198053

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-1-methyl-2-{1-methyl-9H-pyrido[3,4-b]indol-4-yl}pyrrolidine

> <ALOGPS_LOGP>
3.10

> <JCHEM_LOGP>
2.4115447349999997

> <ALOGPS_LOGS>
-3.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.380124838412573

> <JCHEM_PKA_STRONGEST_BASIC>
9.212046783093632

> <JCHEM_POLAR_SURFACE_AREA>
31.92

> <JCHEM_REFRACTIVITY>
81.6607

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
brevicolline

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.410   2.235   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       6.362  -0.695   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.856  -0.374   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.380   1.090   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       3.610  -1.280   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       0.858  -0.695   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -0.173   0.450   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.285   3.699   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       1.380   4.945   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       2.285   6.191   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.750   5.715   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.750   4.175   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.160   4.945   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.382  -2.159   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    5                                                       
CONECT   10    8   11   20                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14                                                       
CONECT   19   15                                                            
CONECT   20   10                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Value	Source
(S)-Brevicolline	MeSH

Chemical Formula

C₁₇H₁₉N₃

Average Mass

265.3600 Da

Monoisotopic Mass

265.15790 Da

IUPAC Name

(2S)-1-methyl-2-{1-methyl-9H-pyrido[3,4-b]indol-4-yl}pyrrolidine

Traditional Name

brevicolline

CAS Registry Number

Not Available

SMILES

CN1CCC[C@H]1C1=CN=C(C)C2=C1C1=C(N2)C=CC=C1

InChI Identifier

InChI=1S/C17H19N3/c1-11-17-16(12-6-3-4-7-14(12)19-17)13(10-18-11)15-8-5-9-20(15)2/h3-4,6-7,10,15,19H,5,8-9H2,1-2H3/t15-/m0/s1

InChI Key

DIZAFWUMCZPYGF-HNNXBMFYSA-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
Carex brevicollis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Harmala alkaloids

Sub Class

Not Available

Direct Parent

Harmala alkaloids

Alternative Parents

Substituents

Harman
Beta-carboline
Pyridoindole
Pyrrolidinylpyridine
Indole
Indole or derivatives
Methylpyridine
Aralkylamine
Pyridine
Benzenoid
N-alkylpyrrolidine
Heteroaromatic compound
Pyrrolidine
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Amine
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

harmala alkaloid (CHEBI:3174 )
Indole alkaloids (C09083 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	3.1	ALOGPS
logP	2.41	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	13.38	ChemAxon
pKa (Strongest Basic)	9.21	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	31.92 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	81.66 m³·mol⁻¹	ChemAxon
Polarizability	30.74 Å³	ChemAxon
Number of Rings	4	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00001694

Chemspider ID

4444722

KEGG Compound ID

C09083

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281361

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Busque J, Pedrosa MM, Cabellos B, Muzquiz M: Phenological changes in the concentration of alkaloids of Carex brevicollis in an Alpine rangeland. J Chem Ecol. 2010 Nov;36(11):1244-54. doi: 10.1007/s10886-010-9865-4. Epub 2010 Oct 5. [PubMed:20890795 ]
Wagner FF, Comins DL: Six-step synthesis of (S)-brevicolline from (S)-nicotine. Org Lett. 2006 Aug 3;8(16):3549-52. doi: 10.1021/ol061334h. [PubMed:16869657 ]

Showing NP-Card for Brevicolline (NP0050840)

MOL for NP0050840 (Brevicolline)

3D MOL for NP0050840 (Brevicolline)

3D SDF for NP0050840 (Brevicolline)

3D-SDF for NP0050840 (Brevicolline)

PDB for NP0050840 (Brevicolline)

3D PDB for NP0050840 (Brevicolline)

SMILES for NP0050840 (Brevicolline)

INCHI for NP0050840 (Brevicolline)

Structure for NP0050840 (Brevicolline)

3D Structure for NP0050840 (Brevicolline)