NP-MRD: Showing NP-Card for Leucolusine (NP0332330)

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Record Information

Version

2.0

Created at

2024-01-04 12:01:12 UTC

Updated at

2025-02-11 15:47:07 UTC

NP-MRD ID

NP0332330

Natural Product DOI

https://doi.org/10.57994/1532

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Leucolusine

Description

Melokhanine A belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Leucolusine was first documented in 2016 (PMID: 27584856). Based on a literature review very few articles have been published on Melokhanine A (PMID: 38284153).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01042412012D          

 25 28  0  0  1  0            999 V2000
    2.8069   -1.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2485   -2.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4115   -3.3785    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6928   -3.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5128   -4.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7256   -4.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1183   -4.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2983   -3.4718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0855   -3.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7233   -2.0476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7846   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0862    1.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8399    1.9810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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  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
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
 10  9  1  0  0  0  0
 10  2  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  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
 15 19  1  6  0  0  0
 15 20  1  0  0  0  0
 20 18  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 14 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332330

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12OCC[C@@]1(CC)CCCN2CC[C@]1(O)C(=O)NC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C19H26N2O3/c1-2-18-8-5-11-21(17(18)24-13-10-18)12-9-19(23)14-6-3-4-7-15(14)20-16(19)22/h3-4,6-7,17,23H,2,5,8-13H2,1H3,(H,20,22)/t17-,18+,19+/m0/s1

> <INCHI_KEY>
FQCHUCFOOQKMIL-IPMKNSEASA-N

> <FORMULA>
C19H26N2O3

> <MOLECULAR_WEIGHT>
330.428

> <EXACT_MASS>
330.194342705

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.78862528140557

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-3-{2-[(3aR,7aS)-3a-ethyl-octahydrofuro[2,3-b]pyridin-7-yl]ethyl}-3-hydroxy-2,3-dihydro-1H-indol-2-one

> <JCHEM_LOGP>
2.354732070999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.775786171773756

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.647148765176544

> <JCHEM_PKA_STRONGEST_BASIC>
7.070676638217647

> <JCHEM_POLAR_SURFACE_AREA>
61.8

> <JCHEM_REFRACTIVITY>
93.4345

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-{2-[(3aR,7aS)-3a-ethyl-hexahydrofuro[2,3-b]pyridin-7-yl]ethyl}-3-hydroxy-1H-indol-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-JAN-24   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JAN-24         0                                  
HETATM    1  O   UNK     0       5.240  -3.663   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.197  -4.797   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       4.502  -6.307   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       3.160  -7.063   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.824  -8.566   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.354  -9.026   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.221  -7.984   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.557  -6.481   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.026  -6.020   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.350  -3.822   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.465  -0.476   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.370   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.465   2.016   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   20  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.161   3.072   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.568   3.698   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9    2   11   12                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   25                                                  
CONECT   15   14   16   19   20                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   20                                                       
CONECT   19   15                                                            
CONECT   20   15   18   21   23                                             
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   14                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₆N₂O₃

Average Mass

330.4280 Da

Monoisotopic Mass

330.19434 Da

IUPAC Name

(3R)-3-{2-[(3aR,7aS)-3a-ethyl-octahydrofuro[2,3-b]pyridin-7-yl]ethyl}-3-hydroxy-2,3-dihydro-1H-indol-2-one

Traditional Name

(3R)-3-{2-[(3aR,7aS)-3a-ethyl-hexahydrofuro[2,3-b]pyridin-7-yl]ethyl}-3-hydroxy-1H-indol-2-one

CAS Registry Number

Not Available

SMILES

[H][C@]12OCC[C@@]1(CC)CCCN2CC[C@]1(O)C(=O)NC2=CC=CC=C12

InChI Identifier

InChI=1S/C19H26N2O3/c1-2-18-8-5-11-21(17(18)24-13-10-18)12-9-19(23)14-6-3-4-7-15(14)20-16(19)22/h3-4,6-7,17,23H,2,5,8-13H2,1H3,(H,20,22)/t17-,18+,19+/m0/s1

InChI Key

FQCHUCFOOQKMIL-IPMKNSEASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C3D6O, experimental)	yylow@um.edu.my	Not Available	Not Available	2024-01-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C3D6O, experimental)	yylow@um.edu.my	Not Available	Not Available	2024-01-04	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.133706048, C3D6O, simulated)	yylow@um.edu.my	Department of Chemistry, Faculty of Science, Universiti Malaya	Yun-Yee Low	2024-05-14	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Leuconotis eugeniifolia		Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Benzenoid
Piperidine
Cyclic carboximidic acid
Tetrahydrofuran
Tertiary alcohol
Hemiaminal
Oxacycle
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Alcohol
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	2.35	ChemAxon
pKa (Strongest Acidic)	11.65	ChemAxon
pKa (Strongest Basic)	7.07	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	61.8 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	93.43 m³·mol⁻¹	ChemAxon
Polarizability	36.79 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

Not Available

Chemspider ID

76777404

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

132524062

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cheng GG, Li D, Hou B, Li XN, Liu L, Chen YY, Lunga PK, Khan A, Liu YP, Zuo ZL, Luo XD: Melokhanines A-J, Bioactive Monoterpenoid Indole Alkaloids with Diverse Skeletons from Melodinus khasianus. J Nat Prod. 2016 Sep 23;79(9):2158-66. doi: 10.1021/acs.jnatprod.6b00011. Epub 2016 Sep 1. [PubMed:27584856 ]
Tan YS, Ng MP, Tan CH, Tang WK, Sim KS, Yong KT, Krishnan P, Lim KH, Lim SH, Low YY: Quinoline, Indole, and Isogranatanine Alkaloids from Malayan Leuconotis eugeniifolia. J Nat Prod. 2024 Feb 23;87(2):286-296. doi: 10.1021/acs.jnatprod.3c00960. Epub 2024 Jan 29. [PubMed:38284153 ]
DOI: 10.1021/acs.jnatprod.3c00960

Showing NP-Card for Leucolusine (NP0332330)

MOL for NP0332330 (Leucolusine)

3D MOL for NP0332330 (Leucolusine)

3D SDF for NP0332330 (Leucolusine)

3D-SDF for NP0332330 (Leucolusine)

PDB for NP0332330 (Leucolusine)

3D PDB for NP0332330 (Leucolusine)

SMILES for NP0332330 (Leucolusine)

INCHI for NP0332330 (Leucolusine)

Structure for NP0332330 (Leucolusine)

3D Structure for NP0332330 (Leucolusine)