NP-MRD: Showing NP-Card for (+)-11-chloromelodinine E (NP0332518)

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Record Information

Version

2.0

Created at

2024-02-20 00:00:38 UTC

Updated at

2024-09-03 04:19:29 UTC

NP-MRD ID

NP0332518

Natural Product DOI

https://doi.org/10.57994/1772

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-11-chloromelodinine E

Description

(+)-11-Chloromelodinine E belongs to the class of organic compounds known as rhazinilam alkaloids. These are alkaloids with a structure based on the rhazinilam skeleton, a tetracyclic compound with a complex tetracyclic carbon skeleton containing pyrrole ring embedded in its indolizine core. (+)-11-chloromelodinine E was first documented in 2024 (PMID: 38341161). Based on a literature review very few articles have been published on (+)-11-chloromelodinine E.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02202400002D          

 24 28  0  0  1  0            999 V2000
    0.1502   -3.1846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6533   -2.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4795   -1.6880    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2848   -1.2699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2427   -0.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7227   -0.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3047   -0.6927    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3636   -0.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3172    0.2631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1694    0.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6865    1.1484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2287   -0.2474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7342   -0.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2764   -1.2523    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7553   -0.3398    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5431   -0.5464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2238   -0.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9678   -0.4370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0310   -1.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3502   -1.7256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6062   -1.3690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8696   -1.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4845   -2.5464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8680   -3.3148    0.0000 Cl  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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  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  2  0  0  0  0
  7 12  1  6  0  0  0
 12 13  1  0  0  0  0
  7 14  1  0  0  0  0
 14  3  1  6  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  2  0  0  0  0
  2 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332518

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@]12CCCN3C(=O)C(Cl)=C4C5=CC=CC=C5N(C(=O)CC1)[C@@]234

> <INCHI_IDENTIFIER>
InChI=1S/C19H19ClN2O2/c1-2-18-9-5-11-21-17(24)16(20)15-12-6-3-4-7-13(12)22(19(15,18)21)14(23)8-10-18/h3-4,6-7H,2,5,8-11H2,1H3/t18-,19+/m1/s1

> <INCHI_KEY>
FINOUIGFWOEBPK-MOPGFXCFSA-N

> <FORMULA>
C19H19ClN2O2

> <MOLECULAR_WEIGHT>
342.82

> <EXACT_MASS>
342.1135056

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
35.16995486870563

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(15R,19R)-9-chloro-15-ethyl-1,11-diazapentacyclo[9.7.1.0^{2,7}.0^{8,19}.0^{15,19}]nonadeca-2,4,6,8-tetraene-10,18-dione

> <JCHEM_LOGP>
3.0232348966666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6874469198015793

> <JCHEM_POLAR_SURFACE_AREA>
40.620000000000005

> <JCHEM_REFRACTIVITY>
91.9537

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(15R,19R)-9-chloro-15-ethyl-1,11-diazapentacyclo[9.7.1.0^{2,7}.0^{8,19}.0^{15,19}]nonadeca-2,4,6,8-tetraene-10,18-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-FEB-24   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-FEB-24         0                                  
HETATM    1  O   UNK     0       0.280  -5.945   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.220  -4.636   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       0.895  -3.151   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -0.532  -2.371   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.453  -0.803   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.349  -0.159   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.435  -1.293   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.679  -1.247   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.592   0.491   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.183   0.800   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.148   2.144   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.427  -0.462   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.371  -1.187   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.383  -2.338   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       3.277  -0.634   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       4.747  -1.020   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.018  -0.150   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.407  -0.816   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.525  -2.351   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.254  -3.221   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.865  -2.555   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.490  -3.344   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.771  -4.753   0.000  0.00  0.00           C+0
HETATM   24 Cl   UNK     0       3.487  -6.188   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12   14                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10                                                            
CONECT   12    7   13                                                       
CONECT   13   12                                                            
CONECT   14    7    3   15   22                                             
CONECT   15   14   10   16                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16   22                                                  
CONECT   22   21   14   23                                                  
CONECT   23   22    2   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₁₉ClN₂O₂

Average Mass

342.8200 Da

Monoisotopic Mass

342.11351 Da

IUPAC Name

(15R,19R)-9-chloro-15-ethyl-1,11-diazapentacyclo[9.7.1.0^{2,7}.0^{8,19}.0^{15,19}]nonadeca-2,4,6,8-tetraene-10,18-dione

Traditional Name

(15R,19R)-9-chloro-15-ethyl-1,11-diazapentacyclo[9.7.1.0^{2,7}.0^{8,19}.0^{15,19}]nonadeca-2,4,6,8-tetraene-10,18-dione

CAS Registry Number

Not Available

SMILES

CC[C@@]12CCCN3C(=O)C(Cl)=C4C5=CC=CC=C5N(C(=O)CC1)[C@@]234

InChI Identifier

InChI=1S/C19H19ClN2O2/c1-2-18-9-5-11-21-17(24)16(20)15-12-6-3-4-7-13(12)22(19(15,18)21)14(23)8-10-18/h3-4,6-7H,2,5,8-11H2,1H3/t18-,19+/m1/s1

InChI Key

FINOUIGFWOEBPK-MOPGFXCFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D_DEPT NMR	¹³C NMR Spectrum (1D, 101 MHz, C3D6O, experimental)	ren.41@osu.edu	The Ohio State University	Yulin Ren	2024-05-02	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 101 MHz, C3D6O, experimental)	ren.41@osu.edu	The Ohio State University	Yulin Ren	2024-05-02	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, C3D6O, experimental)	ren.41@osu.edu	The Ohio State University	Yulin Ren	2024-02-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, C3D6O, experimental)	ren.41@osu.edu	The Ohio State University	Yulin Ren	2024-02-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C3D6O, experimental)	ren.41@osu.edu	The Ohio State University	Yulin Ren	2024-02-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
dubia		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as rhazinilam alkaloids. These are alkaloids with a structure based on the rhazinilam skeleton, a tetracyclic compound with a complex tetracyclic carbon skeleton containing pyrrole ring embedded in its indolizine core.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Rhazinilam alkaloids

Sub Class

Not Available

Direct Parent

Rhazinilam alkaloids

Alternative Parents

Substituents

Rhazinilam skeleton
Pyrroloindole
Diazanaphthalene
Naphthyridine
Azaspirodecane
N-acyl-piperidine
Indolizidine
Indole or derivatives
Indole
N-acylpyrrolidine
Piperidinone
Delta-lactam
Benzenoid
Piperidine
N-acyl-amine
Tertiary carboxylic acid amide
Pyrroline
Pyrrolidine
Pyrrole
Lactam
Carboxamide group
Azacycle
Chloroalkene
Haloalkene
Organoheterocyclic compound
Vinyl halide
Vinyl chloride
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	3.02	ChemAxon
pKa (Strongest Basic)	-0.69	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.62 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	91.95 m³·mol⁻¹	ChemAxon
Polarizability	35.17 Å³	ChemAxon
Number of Rings	5	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ren Y, Kaweesa EN, Henkin JM, Sydara K, Xayvue M, Pandey P, Chittiboyina AG, Ali Z, Ferreira D, Soejarto DD, Burdette JE, Kinghorn AD: Cytotoxic leuconoxine-type diazaspiroindole alkaloids isolated from Cryptolepis dubia. Bioorg Med Chem Lett. 2024 Mar 15;101:129650. doi: 10.1016/j.bmcl.2024.129650. Epub 2024 Feb 9. [PubMed:38341161 ]

Showing NP-Card for (+)-11-chloromelodinine E (NP0332518)

MOL for NP0332518 ((+)-11-chloromelodinine E)

3D MOL for NP0332518 ((+)-11-chloromelodinine E)

3D SDF for NP0332518 ((+)-11-chloromelodinine E)

3D-SDF for NP0332518 ((+)-11-chloromelodinine E)

PDB for NP0332518 ((+)-11-chloromelodinine E)

3D PDB for NP0332518 ((+)-11-chloromelodinine E)

SMILES for NP0332518 ((+)-11-chloromelodinine E)

INCHI for NP0332518 ((+)-11-chloromelodinine E)

Structure for NP0332518 ((+)-11-chloromelodinine E)

3D Structure for NP0332518 ((+)-11-chloromelodinine E)