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Showing NP-Card for 17-O-deacetylvindoline (NP0339790)

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Record Information
Version2.0
Created at2024-09-11 23:34:20 UTC
Updated at2024-09-11 23:34:20 UTC
NP-MRD IDNP0339790
Secondary Accession NumbersNone
Natural Product Identification
Common Name17-O-deacetylvindoline
Description17-O-deacetylvindoline 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. 17-O-deacetylvindoline was first documented in 1985 (PMID: 24254077). Based on a literature review a small amount of articles have been published on 17-O-deacetylvindoline (PMID: 24232684) (PMID: 24254076).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0339790 (17-O-deacetylvindoline)


  Mrv2104 05272302062D          

 30 34  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
    0.7705   -1.1198    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
    1.6709   -2.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0304   -2.7493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6536   -3.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4970   -4.0999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1202   -4.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4333   -3.0204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2598   -2.4544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3808   -2.9743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6062   -3.4569    0.0000 O   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
    2.8597   -1.6221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2757   -1.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4884   -0.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2851   -0.0279    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
    4.8784    0.4008    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
    2.8612   -3.0923    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
    1.6095   -0.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6406   -0.3051    0.0000 N   0  3  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
   -0.7705   -0.5302    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
  1  2  1  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
  6  7  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
  8 11  2  0  0  0  0
  7 12  1  0  0  0  0
  3 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7 14  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  5 17  1  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  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  2  0  0  0  0
 16 23  1  0  0  0  0
 15 24  1  0  0  0  0
  5 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  4 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
  3 30  1  0  0  0  0
M  CHG  1  27   1
M  RAD  1  27   2
M  END
Download

3D MOL for NP0339790 (17-O-deacetylvindoline)

Download
3D SDF for NP0339790 (17-O-deacetylvindoline)

  Mrv2104 05272302062D          

 30 34  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
    0.7705   -1.1198    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
    1.6709   -2.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0304   -2.7493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6536   -3.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4970   -4.0999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1202   -4.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4333   -3.0204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2598   -2.4544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3808   -2.9743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6062   -3.4569    0.0000 O   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
    2.8597   -1.6221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2757   -1.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4884   -0.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2851   -0.0279    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
    4.8784    0.4008    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
    2.8612   -3.0923    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
    1.6095   -0.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6406   -0.3051    0.0000 N   0  3  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
   -0.7705   -0.5302    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
  1  2  1  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
  6  7  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
  8 11  2  0  0  0  0
  7 12  1  0  0  0  0
  3 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7 14  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  5 17  1  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  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  2  0  0  0  0
 16 23  1  0  0  0  0
 15 24  1  0  0  0  0
  5 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  4 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
  3 30  1  0  0  0  0
M  CHG  1  27   1
M  RAD  1  27   2
M  END
> <DATABASE_ID>
NP0339790

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC12C=CC[N+]3CCC4(C(N(C)C5=C4C=CC(OC)=C5)C(O)(C1O)C(=O)OC)C23

> <INCHI_IDENTIFIER>
InChI=1/C23H30N2O5/c1-5-21-9-6-11-25-12-10-22(17(21)25)15-8-7-14(29-3)13-16(15)24(2)18(22)23(28,19(21)26)20(27)30-4/h6-9,13,17-19,26,28H,5,10-12H2,1-4H3/q+1

> <INCHI_KEY>
UGWNULLIAGYONC-UHFFFAOYNA-N

> <FORMULA>
C23H30N2O5

> <MOLECULAR_WEIGHT>
414.501

> <EXACT_MASS>
414.214923494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
44.42715618730216

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12-ethyl-10,11-dihydroxy-5-methoxy-10-(methoxycarbonyl)-8-methyl-8,16lambda5-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,13-tetraen-16-ylium-16-yl

> <JCHEM_LOGP>
-1.839461855138412

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.845894922403676

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.878443286730864

> <JCHEM_PKA_STRONGEST_BASIC>
-0.307346322414451

> <JCHEM_POLAR_SURFACE_AREA>
92.82000000000001

> <JCHEM_REFRACTIVITY>
113.1466

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
12-ethyl-10,11-dihydroxy-5-methoxy-10-(methoxycarbonyl)-8-methyl-8,16lambda5-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,13-tetraen-16-ylium-16-yl

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0339790 (17-O-deacetylvindoline)
Download
PDB for NP0339790 (17-O-deacetylvindoline)
HEADER    PROTEIN                                 27-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-23         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       1.438  -2.090   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.877  -2.641   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.119  -4.162   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.923  -5.132   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.087  -6.141   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.794  -7.653   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.958  -8.662   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.542  -5.638   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.485  -4.582   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.711  -5.552   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.132  -6.453   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       4.640  -4.401   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       5.338  -3.028   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.248  -1.940   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.645  -0.452   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.132  -0.052   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.222  -1.140   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.709  -0.740   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.106   0.748   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.825  -2.628   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.341  -5.772   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.844  -1.443   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.004  -0.152   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       1.196  -0.570   0.000  0.00  0.00           N+1
HETATM   28  C   UNK     0      -0.243  -0.019   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.438  -0.990   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.196  -2.510   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   12   30                                             
CONECT    4    3    5   27                                                  
CONECT    5    4    6   17   25                                             
CONECT    6    5    7   15                                                  
CONECT    7    6    8   12   14                                             
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8                                                            
CONECT   12    7    3   13                                                  
CONECT   13   12                                                            
CONECT   14    7                                                            
CONECT   15    6   16   24                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16    5   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   16                                                       
CONECT   24   15                                                            
CONECT   25    5   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26    4   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29    3                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

Download
3D PDB for NP0339790 (17-O-deacetylvindoline)
Download
SMILES for NP0339790 (17-O-deacetylvindoline)
CCC12C=CC[N+]3CCC4(C(N(C)C5=C4C=CC(OC)=C5)C(O)(C1O)C(=O)OC)C23
Download
INCHI for NP0339790 (17-O-deacetylvindoline)
InChI=1/C23H30N2O5/c1-5-21-9-6-11-25-12-10-22(17(21)25)15-8-7-14(29-3)13-16(15)24(2)18(22)23(28,19(21)26)20(27)30-4/h6-9,13,17-19,26,28H,5,10-12H2,1-4H3/q+1
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View in JSmol
SynonymsNot Available
Chemical FormulaC23H30N2O5
Average Mass414.5010 Da
Monoisotopic Mass414.21492 Da
IUPAC Name12-ethyl-10,11-dihydroxy-5-methoxy-10-(methoxycarbonyl)-8-methyl-8,16lambda5-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,13-tetraen-16-ylium-16-yl
Traditional Name12-ethyl-10,11-dihydroxy-5-methoxy-10-(methoxycarbonyl)-8-methyl-8,16lambda5-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,13-tetraen-16-ylium-16-yl
CAS Registry NumberNot Available
SMILES
CCC12C=CC[N+]3CCC4(C(N(C)C5=C4C=CC(OC)=C5)C(O)(C1O)C(=O)OC)C23
InChI Identifier
InChI=1/C23H30N2O5/c1-5-21-9-6-11-25-12-10-22(17(21)25)15-8-7-14(29-3)13-16(15)24(2)18(22)23(28,19(21)26)20(27)30-4/h6-9,13,17-19,26,28H,5,10-12H2,1-4H3/q+1
InChI KeyUGWNULLIAGYONC-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds  
Super ClassAlkaloids and derivatives  
ClassPlumeran-type alkaloids  
Sub ClassNot Available
Direct ParentPlumeran-type alkaloids  
Alternative Parents
Substituents
  • Plumeran-type alkaloid
    • 

  • Carbazole
    • 

  • Indole or derivatives
    • 

  • Anisole
    • 

  • Dialkylarylamine
    • 

  • Tertiary aliphatic/aromatic amine
    • 

  • Alkyl aryl ether
    • 

  • Beta-hydroxy acid
    • 

  • Aralkylamine
    • 

  • Hydroxy acid
    • 

  • N-alkylpyrrolidine
    • 

  • Benzenoid
    • 

  • Methyl ester
    • 

  • Tertiary alcohol
    • 

  • Pyrrolidine
    • 

  • Cyclic alcohol
    • 

  • Tertiary amine
    • 

  • Amino acid or derivatives
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid ester
    • 

  • 1,2-diol
    • 

  • Organoheterocyclic compound
    • 

  • Carboxylic acid derivative
    • 

  • Azacycle
    • 

  • Ether
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Alcohol
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Amine
    • 

  • Organonitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic nitrogen compound
    • 

  • Organic cation
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.8ChemAxon
pKa (Strongest Acidic)10.88ChemAxon
pKa (Strongest Basic)-0.31ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area92.82 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity113.15 m³·mol⁻¹ChemAxon
Polarizability44.43 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Fahn W, Laussermair E, Deus-Neumann B, Stockigt J: Late enzymes of vindoline biosynthesis : S-Adenosyl-L-methionine: 11-O-demethyl-17-O-deacetylvindoline 11-O-methyltransferase and unspecific acetylesterase. Plant Cell Rep. 1985 Dec;4(6):337-40. doi: 10.1007/BF00269893. [PubMed:24254077  ] 
  2. Fahn W, Stockigt J: Purification of acetyl-CoA: 17-O-deacetylvindoline 17-O-acetyltransferase from Catharanthus roseus leaves. Plant Cell Rep. 1990 Mar;8(10):613-6. doi: 10.1007/BF00270066. [PubMed:24232684  ] 
  3. Fahn W, Gundlach H, Deus-Neumann B, Stockigt J: Late enzymes of vindoline biosynthesis. Acetyl-CoA: 17-O-deacetylvindoline 17-O-acetyl-transferase. Plant Cell Rep. 1985 Dec;4(6):333-6. doi: 10.1007/BF00269892. [PubMed:24254076  ]