NP-MRD: Showing NP-Card for Cephaeline (NP0050959)

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Record Information

Version

2.0

Created at

2022-04-27 22:25:40 UTC

Updated at

2022-04-27 22:25:40 UTC

NP-MRD ID

NP0050959

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cephaeline

Description

Cephaeline, also known as desmethyl-emetine, belongs to the class of organic compounds known as emetine alkaloids. These are alkaloids with a structure characterized by the presence of both an isoquinoline and a benzoquinolizidine nuclei. Cephaeline is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Cephaeline is found in Alangium lamarckii, Alangium longiflorum, Carapichea affinis, Cephaelis acuminata, Cephaelis ipecacuanha , Cephalis ipecacuanha, Dorstenia asaroides, Dorstenia bahiensis, Dorstenia barnimiana, Dorstenia brasiliensis , Dorstenia bryonifolia, Dorstenia cayapiaa, Dorstenia contrajerva , Dorstenia drakena , Dorstenia excentria, Dorstenia heringerii, Dorstenia lindeniana, Dorstenia psilurus, Pogonopus tubulosus, Psychotria borucana, Psychotria burucana, Psychotria ipecacuanha and Psychotria klugii. Cephaeline was first documented in 2021 (PMID: 35295737). Based on a literature review a small amount of articles have been published on cephaeline (PMID: 35355337) (PMID: 35301800) (PMID: 34800440) (PMID: 34797299).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200252D          

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M  END

     RDKit          3D

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  Mrv1652304282200252D          

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 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
 28 30  1  0  0  0  0
 27 31  1  0  0  0  0
 31 32  1  0  0  0  0
 16 33  1  6  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050959

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1CN2CCC3=C(C=C(OC)C(OC)=C3)[C@@H]2C[C@@H]1C[C@H]1NCCC2=C1C=C(OC)C(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C28H38N2O4/c1-5-17-16-30-9-7-19-13-27(33-3)28(34-4)15-22(19)24(30)11-20(17)10-23-21-14-26(32-2)25(31)12-18(21)6-8-29-23/h12-15,17,20,23-24,29,31H,5-11,16H2,1-4H3/t17-,20-,23+,24-/m0/s1

> <INCHI_KEY>
DTGZHCFJNDAHEN-OZEXIGSWSA-N

> <FORMULA>
C28H38N2O4

> <MOLECULAR_WEIGHT>
466.622

> <EXACT_MASS>
466.283157712

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
54.462857526684054

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R)-1-{[(2S,3R,11bS)-3-ethyl-9,10-dimethoxy-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-yl]methyl}-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol

> <ALOGPS_LOGP>
4.10

> <JCHEM_LOGP>
3.950451670283629

> <ALOGPS_LOGS>
-4.84

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.087153557619692

> <JCHEM_PKA_STRONGEST_BASIC>
9.150666029736596

> <JCHEM_POLAR_SURFACE_AREA>
63.19000000000001

> <JCHEM_REFRACTIVITY>
135.26839999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.73e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cephaeline

> <JCHEM_VEBER_RULE>
0

$$$$

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      -9.336   6.930   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -9.336   8.470   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0     -10.669   9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -12.003   8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -12.003   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.669   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -10.669   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -12.003   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -13.337   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -13.337   6.160   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0     -14.670   3.850   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0     -16.004   4.620   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0     -12.003   2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0     -13.337   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.668   8.470   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      -6.668   3.850   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
CONECT    1    2    6   18                                                  
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    5                                                       
CONECT   11    9   12                                                       
CONECT   12   11                                                            
CONECT   13    8   14                                                       
CONECT   14   13                                                            
CONECT   15    2   16                                                       
CONECT   16   15   17   33                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17    1                                                       
CONECT   19   17   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   20   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   31                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28   24                                                       
CONECT   30   28                                                            
CONECT   31   27   32                                                       
CONECT   32   31                                                            
CONECT   33   16   34                                                       
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
Cephaelin	ChEBI
Cephaline	MeSH
Desmethyl-emetine	MeSH
Desmethylemetine	MeSH

Chemical Formula

C₂₈H₃₈N₂O₄

Average Mass

466.6220 Da

Monoisotopic Mass

466.28316 Da

IUPAC Name

(1R)-1-{[(2S,3R,11bS)-3-ethyl-9,10-dimethoxy-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-yl]methyl}-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol

Traditional Name

cephaeline

CAS Registry Number

Not Available

SMILES

CC[C@H]1CN2CCC3=C(C=C(OC)C(OC)=C3)[C@@H]2C[C@@H]1C[C@H]1NCCC2=C1C=C(OC)C(O)=C2

InChI Identifier

InChI=1S/C28H38N2O4/c1-5-17-16-30-9-7-19-13-27(33-3)28(34-4)15-22(19)24(30)11-20(17)10-23-21-14-26(32-2)25(31)12-18(21)6-8-29-23/h12-15,17,20,23-24,29,31H,5-11,16H2,1-4H3/t17-,20-,23+,24-/m0/s1

InChI Key

DTGZHCFJNDAHEN-OZEXIGSWSA-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
Alangium lamarckii	Plant	KNApSAcK
Alangium longiflorum	Plant	KNApSAcK
Carapichea affinis	-	KNApSAcK
Cephaelis acuminata	Plant	KNApSAcK
Cephaelis ipecacuanha	Plant	KNApSAcK
Cephalis ipecacuanha	-	KNApSAcK
Dorstenia asaroides	Plant	KNApSAcK
Dorstenia bahiensis	Plant	KNApSAcK
Dorstenia barnimiana	Plant	KNApSAcK
Dorstenia brasiliensis	Plant	KNApSAcK
Dorstenia bryonifolia	Plant	KNApSAcK
Dorstenia cayapiaa	Plant	KNApSAcK
Dorstenia contrajerva	Plant	KNApSAcK
Dorstenia drakena	Plant	KNApSAcK
Dorstenia excentria	Plant	KNApSAcK
Dorstenia heringerii	Plant	KNApSAcK
Dorstenia lindeniana	Plant	KNApSAcK
Dorstenia psilurus	Plant	KNApSAcK
Pogonopus tubulosus	LOTUS Database	35616633
Psychotria borucana	LOTUS Database	35616633
Psychotria burucana	Plant	KNApSAcK
Psychotria ipecacuanha	Plant	KNApSAcK
Psychotria klugii	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as emetine alkaloids. These are alkaloids with a structure characterized by the presence of both an isoquinoline and a benzoquinolizidine nuclei.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Emetine alkaloids

Sub Class

Not Available

Direct Parent

Emetine alkaloids

Alternative Parents

Substituents

Emetine alkaloid
Quinolizidine
Tetrahydroisoquinoline
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Piperidine
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Secondary aliphatic amine
Ether
Azacycle
Secondary amine
Organoheterocyclic compound
Organonitrogen compound
Amine
Organopnictogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pyridoisoquinoline (CHEBI:3533 )
Isoquinoline alkaloids (C09390 )

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	4.1	ALOGPS
logP	3.95	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	10.09	ChemAxon
pKa (Strongest Basic)	9.15	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.19 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	135.27 m³·mol⁻¹	ChemAxon
Polarizability	54.46 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00001835

Chemspider ID

390702

KEGG Compound ID

C09390

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cephaeline

METLIN ID

Not Available

PubChem Compound

442195

PDB ID

Not Available

ChEBI ID

3533

Good Scents ID

Not Available

References

General References

Gonzalez BL, de Oliveira NC, Ritter MR, Tonin FS, Melo EB, Sanches ACC, Fernandez-Llimos F, Petruco MV, de Mello JCP, Chierrito D, de Medeiros Araujo DC: The naturally-derived alkaloids as a potential treatment for COVID-19: A scoping review. Phytother Res. 2022 Mar 30. doi: 10.1002/ptr.7442. [PubMed:35355337 ]
Qiang W, Dai Y, Xing X, Sun X: Identification of a metabolic reprogramming-related signature associated with prognosis and immune microenvironment of head and neck squamous cell carcinoma by in silico analysis. Cancer Med. 2022 Mar 18. doi: 10.1002/cam4.4670. [PubMed:35301800 ]
Pushparaj PN, Kalamegam G, Wali Sait KH, Rasool M: Decoding the Role of Astrocytes in the Entorhinal Cortex in Alzheimer's Disease Using High-Dimensional Single-Nucleus RNA Sequencing Data and Next-Generation Knowledge Discovery Methodologies: Focus on Drugs and Natural Product Remedies for Dementia. Front Pharmacol. 2022 Feb 28;12:720170. doi: 10.3389/fphar.2021.720170. eCollection 2021. [PubMed:35295737 ]
Gulfidan G, Soylu M, Demirel D, Erdonmez HBC, Beklen H, Ozbek Sarica P, Arga KY, Turanli B: Systems biomarkers for papillary thyroid cancer prognosis and treatment through multi-omics networks. Arch Biochem Biophys. 2022 Jan 15;715:109085. doi: 10.1016/j.abb.2021.109085. Epub 2021 Nov 17. [PubMed:34800440 ]
Zhang J, Liu J, Xu S, Yu X, Zhang Y, Li X, Zhang L, Yang J, Xing X: Bioinformatics analyses of the pathogenesis and new biomarkers of chronic obstructive pulmonary disease. Medicine (Baltimore). 2021 Nov 19;100(46):e27737. doi: 10.1097/MD.0000000000027737. [PubMed:34797299 ]

Showing NP-Card for Cephaeline (NP0050959)

MOL for NP0050959 (Cephaeline)

3D MOL for NP0050959 (Cephaeline)

3D SDF for NP0050959 (Cephaeline)

3D-SDF for NP0050959 (Cephaeline)

PDB for NP0050959 (Cephaeline)

3D PDB for NP0050959 (Cephaeline)

SMILES for NP0050959 (Cephaeline)

INCHI for NP0050959 (Cephaeline)

Structure for NP0050959 (Cephaeline)

3D Structure for NP0050959 (Cephaeline)