NP-MRD: Showing NP-Card for Ellipticine (NP0050860)

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Record Information

Version

2.0

Created at

2022-04-27 22:16:32 UTC

Updated at

2022-04-27 22:16:32 UTC

NP-MRD ID

NP0050860

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ellipticine

Description

Ellipticine, also known as NSC 71795, 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. A organic heterotetracyclic compound that is pyridocarbazole carrying two methyl substituents at positions 5 and 11. Ellipticine is found in Aspidosperma subincanum, Bleekeria vitiensis, Elateriospermum tapos, Ochrosia acuminata, Ochrosia elliptica, Ochrosia moorei and Tabernaemontana coffeoides. Ellipticine was first documented in 2012 (PMID: 22802684). Ellipticine is a very strong basic compound (based on its pKa) (PMID: 22917556) (PMID: 23697684) (PMID: 23827542) (PMID: 23869776).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 36  0  0  0  0  0  0  0  0999 V2000
    1.7409    2.7457    0.2358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2578    1.3453    0.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1766    0.3278    0.2159 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5294    0.6048    0.3456 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4242   -0.4171    0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0443   -1.7037    0.3295 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7137   -2.0137    0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7713   -1.0121    0.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4245   -1.3305    0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0143   -2.7439   -0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4801   -0.2855   -0.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0562    1.0216    0.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1124    1.8430   -0.0660 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2354    1.1033   -0.1967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5617    1.4731   -0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5148    0.4914   -0.4497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1597   -0.8381   -0.4471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8287   -1.2264   -0.3184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8767   -0.2567   -0.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0604    2.9994    1.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5308    2.9689   -0.5166 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8933    3.4270   -0.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7972    1.6571    0.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4832   -0.1434    0.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4106   -3.0285    0.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7182   -3.4966    0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4910   -2.9436   -1.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7577   -2.8191    0.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0731    2.8839   -0.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7962    2.5190   -0.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5801    0.7485   -0.5538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8732   -1.6362   -0.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5651   -2.2646   -0.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 19  2  0
 19 18  1  0
 18 17  2  0
 17 16  1  0
 16 15  2  0
 12  2  1  0
 15 14  1  0
  8  3  1  0
 19 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
 10 26  1  0
 10 27  1  0
 10 28  1  0
 13 29  1  0
 18 33  1  0
 17 32  1  0
 16 31  1  0
 15 30  1  0
M  END


  Mrv1533004171503122D          

 19 22  0  0  0  0            999 V2000
    3.4623    2.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2997    1.5030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9189    0.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7006    1.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3198    0.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1571   -0.1327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3754   -0.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7562    0.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9745   -0.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8119   -0.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3553    0.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5359    0.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0583   -0.3374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2369   -0.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1069    0.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3706    1.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1920    1.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7990    1.6440    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5180    1.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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  2  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  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
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 12 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 19  1  0  0  0  0
 11 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0050860

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2C=CN=CC2=C(C)C2=C1NC1=C2C=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H14N2/c1-10-14-9-18-8-7-12(14)11(2)17-16(10)13-5-3-4-6-15(13)19-17/h3-9,19H,1-2H3

> <INCHI_KEY>
CTSPAMFJBXKSOY-UHFFFAOYSA-N

> <FORMULA>
C17H14N2

> <MOLECULAR_WEIGHT>
246.313

> <EXACT_MASS>
246.115698459

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
28.241839242347783

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,11-dimethyl-6H-pyrido[4,3-b]carbazole

> <ALOGPS_LOGP>
4.34

> <JCHEM_LOGP>
3.8895327976666665

> <ALOGPS_LOGS>
-4.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.044886967101736

> <JCHEM_PKA_STRONGEST_BASIC>
5.123435947070323

> <JCHEM_POLAR_SURFACE_AREA>
28.68

> <JCHEM_REFRACTIVITY>
77.84790000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.64e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ellipticine

> <JCHEM_VEBER_RULE>
1

$$$$

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       6.463   4.315   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.159   2.806   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.315   1.788   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.774   2.280   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.930   1.262   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       9.627  -0.248   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       8.167  -0.740   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.012   0.278   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.552  -0.214   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.249  -1.724   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.397   0.804   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.867   0.626   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.976  -0.630   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.442  -0.486   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.200   0.914   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.692   2.170   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.225   2.026   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       3.358   3.069   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       4.700   2.314   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   19                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18    2   11                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

View in JSmol

Synonyms

Value	Source
Elliptisine	ChEBI
NSC 71795	ChEBI
NSC-71795	ChEBI
Ellipticine tartrate	MeSH
5,11-Dimethyl-6H-pyrido(4,3-b)carbazole	MeSH
Ellipticine hydrochloride	MeSH

Chemical Formula

C₁₇H₁₄N₂

Average Mass

246.3130 Da

Monoisotopic Mass

246.11570 Da

IUPAC Name

5,11-dimethyl-6H-pyrido[4,3-b]carbazole

Traditional Name

ellipticine

CAS Registry Number

Not Available

SMILES

CC1=C2C=CN=CC2=C(C)C2=C1NC1=C2C=CC=C1

InChI Identifier

InChI=1S/C17H14N2/c1-10-14-9-18-8-7-12(14)11(2)17-16(10)13-5-3-4-6-15(13)19-17/h3-9,19H,1-2H3

InChI Key

CTSPAMFJBXKSOY-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
Aspidosperma subincanum	Plant	KNApSAcK
Bleekeria vitiensis	Plant	KNApSAcK
Elateriospermum tapos	LOTUS Database	35616633
Ochrosia acuminata	Plant	KNApSAcK
Ochrosia elliptica	Plant	KNApSAcK
Ochrosia moorei	Plant	KNApSAcK
Tabernaemontana coffeoides	LOTUS Database	35616633

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
Isoquinoline
Indole
Benzenoid
Pyridine
Heteroaromatic compound
Pyrrole
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotetracyclic compound (CHEBI:4776 )
indole alkaloid (CHEBI:4776 )
organonitrogen heterocyclic compound (CHEBI:4776 )
polycyclic heteroarene (CHEBI:4776 )
Indole alkaloids (C09154 )

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	4.34	ALOGPS
logP	3.89	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	15.04	ChemAxon
pKa (Strongest Basic)	5.12	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	77.85 m³·mol⁻¹	ChemAxon
Polarizability	28.24 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

C00001716

Chemspider ID

Not Available

KEGG Compound ID

C09154

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ellipticine

METLIN ID

Not Available

PubChem Compound

3213

PDB ID

Not Available

ChEBI ID

4776

Good Scents ID

Not Available

References

General References

Wu Y, Sadatmousavi P, Wang R, Lu S, Yuan YF, Chen P: Self-assembling peptide-based nanoparticles enhance anticancer effect of ellipticine in vitro and in vivo. Int J Nanomedicine. 2012;7:3221-33. doi: 10.2147/IJN.S31858. Epub 2012 Jun 28. [PubMed:22802684 ]
Stiborova M, Poljakova J, Martinkova E, Ulrichova J, Simanek V, Dvorak Z, Frei E: Ellipticine oxidation and DNA adduct formation in human hepatocytes is catalyzed by human cytochromes P450 and enhanced by cytochrome b5. Toxicology. 2012 Dec 16;302(2-3):233-41. doi: 10.1016/j.tox.2012.08.004. Epub 2012 Aug 16. [PubMed:22917556 ]
Ghosh S, Kar A, Chowdhury S, Dasgupta D: Ellipticine binds to a human telomere sequence: an additional mode of action as a putative anticancer agent? Biochemistry. 2013 Jun 18;52(24):4127-37. doi: 10.1021/bi400080t. Epub 2013 Jun 4. [PubMed:23697684 ]
Masood F, Chen P, Yasin T, Fatima N, Hasan F, Hameed A: Encapsulation of Ellipticine in poly-(3-hydroxybutyrate-co-3-hydroxyvalerate) based nanoparticles and its in vitro application. Mater Sci Eng C Mater Biol Appl. 2013 Apr 1;33(3):1054-60. doi: 10.1016/j.msec.2012.11.025. Epub 2012 Nov 28. [PubMed:23827542 ]
Tmejova K, Krejcova L, Hynek D, Adam V, Babula P, Trnkova L, Stiborova M, Eckschlager T, Kizek R: Electrochemical study of ellipticine interaction with single and double stranded oligonucleotides. Anticancer Agents Med Chem. 2014 Feb;14(2):331-40. doi: 10.2174/18715206113139990316. [PubMed:23869776 ]

Showing NP-Card for Ellipticine (NP0050860)

MOL for NP0050860 (Ellipticine)

3D MOL for NP0050860 (Ellipticine)

3D SDF for NP0050860 (Ellipticine)

3D-SDF for NP0050860 (Ellipticine)

PDB for NP0050860 (Ellipticine)

3D PDB for NP0050860 (Ellipticine)

SMILES for NP0050860 (Ellipticine)

INCHI for NP0050860 (Ellipticine)

Structure for NP0050860 (Ellipticine)

3D Structure for NP0050860 (Ellipticine)