NP-MRD: Showing NP-Card for Caceline (NP0050852)

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Record Information

Version

2.0

Created at

2022-04-27 22:15:39 UTC

Updated at

2022-04-27 22:15:39 UTC

NP-MRD ID

NP0050852

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Caceline

Description

Ceceline 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. Caceline is found in Aniba santalodora. Ceceline is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 42  0  0  0  0  0  0  0  0999 V2000
    5.8461   -0.6628   -1.8592 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2444   -1.7148   -1.1345 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0070   -1.4858   -0.5567 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4183   -2.5146    0.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1837   -2.2809    0.7300 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5361   -1.0688    0.6143 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3682   -0.5762    1.0594 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1932    0.7234    0.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8188    1.6310    0.8721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0333    1.2453    1.6450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0404    0.5051    0.8951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9347    1.2007    0.0676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9061    0.5611   -0.6385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0538   -0.8268   -0.5683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0651   -1.4400   -1.3109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1924   -1.5327    0.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1989   -0.8609    0.9539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7219    2.8647    0.3620 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3391    3.2243   -0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3759    2.3473   -0.5893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2897    1.0656   -0.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1165   -0.0393   -0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3486   -0.2781   -0.6652 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9071   -0.8946   -2.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8341    0.2971   -1.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3231   -0.4403   -2.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9344   -3.4851    0.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7393   -3.0900    1.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3124   -1.1155    1.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7061    0.6310    2.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4271    2.2028    2.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8312    2.2626    0.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6016    1.0973   -1.2808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6637   -0.8757   -1.8779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2906   -2.6127    0.3021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5846   -1.4900    1.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3453    4.2426   -0.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2345    2.6321   -1.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7982    0.5514   -1.2254 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 23  2  0
 23 22  1  0
 22  6  2  0
  6  7  1  0
  7  8  1  0
  8 21  2  0
 21 20  1  0
 20 19  2  0
 19 18  1  0
 18  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
 21 22  1  0
 17 11  1  0
  9  8  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
 23 39  1  0
  7 29  1  0
 20 38  1  0
 19 37  1  0
 10 30  1  0
 10 31  1  0
 12 32  1  0
 13 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
  5 28  1  0
  4 27  1  0
M  END


  Mrv1533004171500502D          

 23 26  0  0  0  0            999 V2000
    0.6159   -2.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4229   -2.4457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9749   -1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7200   -1.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720   -0.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7464   -0.1215    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4139   -0.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2208   -0.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4758    0.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2828    0.5213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5377    1.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3447    1.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8967    0.8644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7037    1.0359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6418    0.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8348   -0.0918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7729   -1.0479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5179   -1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7110   -2.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1589   -1.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339   -1.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7819   -2.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 11 17  1  0  0  0  0
  9 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
  8 21  2  0  0  0  0
 21 22  1  0  0  0  0
  6 22  2  0  0  0  0
 22 23  1  0  0  0  0
  3 23  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0050852

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(NC3=C2C=CN=C3CC2=CC=C(O)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H16N2O2/c1-23-14-6-7-17-16(11-14)15-8-9-20-18(19(15)21-17)10-12-2-4-13(22)5-3-12/h2-9,11,21-22H,10H2,1H3

> <INCHI_KEY>
BHOQLEQHXKFSAO-UHFFFAOYSA-N

> <FORMULA>
C19H16N2O2

> <MOLECULAR_WEIGHT>
304.349

> <EXACT_MASS>
304.121177763

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
33.11561886646995

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-({6-methoxy-9H-pyrido[3,4-b]indol-1-yl}methyl)phenol

> <ALOGPS_LOGP>
4.53

> <JCHEM_LOGP>
3.3776866636666663

> <ALOGPS_LOGS>
-4.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.611760524059289

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.976945400901524

> <JCHEM_PKA_STRONGEST_BASIC>
5.3943718208870415

> <JCHEM_POLAR_SURFACE_AREA>
58.14

> <JCHEM_REFRACTIVITY>
89.0728

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.38e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ceceline

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       1.150  -4.245   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.656  -4.565   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.687  -3.421   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.211  -1.956   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.241  -0.812   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.747  -1.132   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       6.993  -0.227   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       8.239  -1.132   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.746  -0.812   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.221   0.653   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.728   0.973   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.204   2.438   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.710   2.758   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.740   1.613   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      16.247   1.934   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      14.265   0.149   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.758  -0.171   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      10.776  -1.956   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      10.300  -3.421   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.794  -3.741   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.763  -2.597   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.223  -2.597   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.193  -3.741   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   22                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   11                                                       
CONECT   18    9   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    8   22                                                  
CONECT   22   21    6   23                                                  
CONECT   23   22    3                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₁₆N₂O₂

Average Mass

304.3490 Da

Monoisotopic Mass

304.12118 Da

IUPAC Name

4-({6-methoxy-9H-pyrido[3,4-b]indol-1-yl}methyl)phenol

Traditional Name

ceceline

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(NC3=C2C=CN=C3CC2=CC=C(O)C=C2)C=C1

InChI Identifier

InChI=1S/C19H16N2O2/c1-23-14-6-7-17-16(11-14)15-8-9-20-18(19(15)21-17)10-12-2-4-13(22)5-3-12/h2-9,11,21-22H,10H2,1H3

InChI Key

BHOQLEQHXKFSAO-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
Aniba santalodora	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
Indole
Indole or derivatives
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Pyridine
Benzenoid
Heteroaromatic compound
Pyrrole
Organoheterocyclic compound
Azacycle
Ether
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

harmala alkaloid (CHEBI:3477 )

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	4.53	ALOGPS
logP	3.38	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	9.98	ChemAxon
pKa (Strongest Basic)	5.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.14 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	89.07 m³·mol⁻¹	ChemAxon
Polarizability	33.12 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

C00001706

Chemspider ID

Not Available

KEGG Compound ID

C09130

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281380

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Caceline (NP0050852)

MOL for NP0050852 (Caceline)

3D MOL for NP0050852 (Caceline)

3D SDF for NP0050852 (Caceline)

3D-SDF for NP0050852 (Caceline)

PDB for NP0050852 (Caceline)

3D PDB for NP0050852 (Caceline)

SMILES for NP0050852 (Caceline)

INCHI for NP0050852 (Caceline)

Structure for NP0050852 (Caceline)

3D Structure for NP0050852 (Caceline)