NP-MRD: Showing NP-Card for Vindoline (NP0137369)

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Record Information

Version

2.0

Created at

2022-05-30 16:50:23 UTC

Updated at

2022-05-30 16:50:23 UTC

NP-MRD ID

NP0137369

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Vindoline

Description

Vindoline belongs to the class of organic compounds known as plumeran-type alkaloids. These are alkaloids with a structure based on the plumeran skeleton. Plumeran is a pentacyclic compound that consists of a pyrrolidine ring shed to the quinoline moiety of pyrido[3,2-c]carbazole ring system. Vindoline is found in Catharanthus roseus and Catharanthus trichophyllus. Vindoline is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231519282D          

 33 37  0  0  0  0            999 V2000
   -1.2812   -1.8647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5107   -2.1596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1299   -1.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6406   -1.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7705   -0.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1299   -0.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6406   -0.3051    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6095   -0.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0595   -0.7730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5410   -1.4147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7705   -1.1198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6709   -2.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4859   -2.3576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8612   -3.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8597   -1.6221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6564   -1.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8690   -0.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6657   -0.3963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2497   -0.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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    3.8465    0.3652    1.6743 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0196    1.8990   -2.2252 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3489    0.0270   -1.4851 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8019    0.8797   -1.1402 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6362    1.0492   -2.2737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4171    2.2550   -0.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7808    3.3074   -1.3056 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004231519282D          

 33 37  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0137369

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC12C=CCN3CCC4(C13)C(N(C)C1=CC(OC)=CC=C41)C(O)(C2OC(C)=O)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C25H32N2O6/c1-6-23-10-7-12-27-13-11-24(19(23)27)17-9-8-16(31-4)14-18(17)26(3)20(24)25(30,22(29)32-5)21(23)33-15(2)28/h7-10,14,19-21,30H,6,11-13H2,1-5H3

> <INCHI_KEY>
CXBGOBGJHGGWIE-UHFFFAOYSA-N

> <FORMULA>
C25H32N2O6

> <MOLECULAR_WEIGHT>
456.539

> <EXACT_MASS>
456.226036758

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
48.772066848644286

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 11-(acetyloxy)-12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,13-tetraene-10-carboxylate

> <ALOGPS_LOGP>
2.53

> <JCHEM_LOGP>
1.8826374543333317

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.868158007477678

> <JCHEM_PKA_STRONGEST_BASIC>
8.673438058558657

> <JCHEM_POLAR_SURFACE_AREA>
88.54

> <JCHEM_REFRACTIVITY>
122.2981

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.92e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 11-(acetyloxy)-12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,13-tetraene-10-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      -2.392  -3.481   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.953  -4.031   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.243  -3.061   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.196  -2.510   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.438  -0.990   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.243  -0.019   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       1.196  -0.570   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       3.004  -0.152   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.844  -1.443   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.877  -2.641   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.438  -2.090   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.119  -4.162   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       4.640  -4.401   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       5.341  -5.772   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.338  -3.028   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.825  -2.628   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.222  -1.140   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.709  -0.740   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.799  -1.827   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.132  -0.052   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.645  -0.452   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.248  -1.940   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.923  -5.132   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.132  -6.453   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.485  -4.582   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.711  -5.552   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.468  -7.073   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.970  -7.623   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.664  -8.043   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.087  -6.141   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.542  -5.638   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       2.794  -7.653   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.958  -8.662   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   11   25                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   22                                             
CONECT   11   10    3    7                                                  
CONECT   12   10   13   23                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   10   15                                                  
CONECT   23   12   24   25   30                                             
CONECT   24   23                                                            
CONECT   25   23    3   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   23   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
Vindoline, citrate, (2beta,3beta,4beta,5alpha,12beta,19alpha)-isomer	MeSH
Vindoline, monohydrochloride, (2beta,3beta,4beta,5alpha,12beta,19alpha)-isomer	MeSH
Methyl 11-(acetyloxy)-12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0,.0,.0,]nonadeca-2(7),3,5,13-tetraene-10-carboxylic acid	Generator

Chemical Formula

C₂₅H₃₂N₂O₆

Average Mass

456.5390 Da

Monoisotopic Mass

456.22604 Da

IUPAC Name

methyl 11-(acetyloxy)-12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,13-tetraene-10-carboxylate

Traditional Name

methyl 11-(acetyloxy)-12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,13-tetraene-10-carboxylate

CAS Registry Number

Not Available

SMILES

CCC12C=CCN3CCC4(C13)C(N(C)C1=CC(OC)=CC=C41)C(O)(C2OC(C)=O)C(=O)OC

InChI Identifier

InChI=1S/C25H32N2O6/c1-6-23-10-7-12-27-13-11-24(19(23)27)17-9-8-16(31-4)14-18(17)26(3)20(24)25(30,22(29)32-5)21(23)33-15(2)28/h7-10,14,19-21,30H,6,11-13H2,1-5H3

InChI Key

CXBGOBGJHGGWIE-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Catharanthus roseus	LOTUS Database	35616633
Catharanthus trichophyllus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as plumeran-type alkaloids. These are alkaloids with a structure based on the plumeran skeleton. Plumeran is a pentacyclic compound that consists of a pyrrolidine ring shed to the quinoline moiety of pyrido[3,2-c]carbazole ring system.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Plumeran-type alkaloids

Sub Class

Not Available

Direct Parent

Plumeran-type alkaloids

Alternative Parents

Substituents

Plumeran-type alkaloid
Carbazole
Indole or derivatives
Anisole
Tertiary aliphatic/aromatic amine
Dialkylarylamine
Alkyl aryl ether
Aralkylamine
N-alkylpyrrolidine
Benzenoid
Dicarboxylic acid or derivatives
Methyl ester
Cyclic alcohol
Tertiary alcohol
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Ether
Organic nitrogen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organopnictogen compound
Amine
Organic oxygen compound
Organooxygen compound
Organonitrogen 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	2.53	ALOGPS
logP	1.88	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	10.87	ChemAxon
pKa (Strongest Basic)	8.67	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	88.54 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	122.3 m³·mol⁻¹	ChemAxon
Polarizability	48.77 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	Yes	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

Vindoline

METLIN ID

Not Available

PubChem Compound

425978

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Vindoline (NP0137369)

MOL for NP0137369 (Vindoline)

3D MOL for NP0137369 (Vindoline)

3D SDF for NP0137369 (Vindoline)

3D-SDF for NP0137369 (Vindoline)

PDB for NP0137369 (Vindoline)

3D PDB for NP0137369 (Vindoline)

SMILES for NP0137369 (Vindoline)

INCHI for NP0137369 (Vindoline)

Structure for NP0137369 (Vindoline)

3D Structure for NP0137369 (Vindoline)