NP-MRD: Showing NP-Card for desacetoxyvindoline (NP0339592)

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Record Information

Version

2.0

Created at

2024-09-11 22:36:40 UTC

Updated at

2024-09-11 22:36:40 UTC

NP-MRD ID

NP0339592

Secondary Accession Numbers

None

Natural Product Identification

Common Name

desacetoxyvindoline

Description

desacetoxyvindoline was first documented in 2006 (PMID: 16895428). Based on a literature review a significant number of articles have been published on desacetoxyvindoline (PMID: 35323487) (PMID: 26813287) (PMID: 21047699) (PMID: 33994597) (PMID: 32886329) (PMID: 29200741).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05272301082D          

 29 33  0  0  0  0            999 V2000
    0.1477    0.2147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9183    0.5096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5589   -0.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6888    0.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4593    1.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0351    1.8069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0999    0.5794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9149    0.7076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2902    1.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2886   -0.0279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0853   -0.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2980   -1.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0946   -1.2537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6786   -0.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7140   -1.6221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9173   -1.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7047   -0.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9700   -0.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4885   -0.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0384   -1.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0695   -1.3449    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -1.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6584   -1.1198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7883   -0.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1995   -0.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0825    1.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8623    1.3704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9259    2.4499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5491    2.9904    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  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
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
  3 24  1  0  0  0  0
 21 25  1  0  0  0  0
  3 25  1  0  0  0  0
 18 25  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END


  Mrv2104 05272301082D          

 29 33  0  0  0  0            999 V2000
    0.1477    0.2147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9183    0.5096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5589   -0.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6888    0.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4593    1.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0351    1.8069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0999    0.5794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9149    0.7076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2902    1.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2886   -0.0279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0853   -0.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2980   -1.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0946   -1.2537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6786   -0.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7140   -1.6221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9173   -1.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7047   -0.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9700   -0.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4885   -0.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0384   -1.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0695   -1.3449    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -1.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6584   -1.1198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7883   -0.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1995   -0.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0825    1.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8623    1.3704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9259    2.4499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5491    2.9904    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  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
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
  3 24  1  0  0  0  0
 21 25  1  0  0  0  0
  3 25  1  0  0  0  0
 18 25  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339592

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC12CC(O)(C3N(C)C4=CC(OC)=CC=C4C33CCN(CC=C1)C23)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1/C23H30N2O4/c1-5-21-9-6-11-25-12-10-22(18(21)25)16-8-7-15(28-3)13-17(16)24(2)19(22)23(27,14-21)20(26)29-4/h6-9,13,18-19,27H,5,10-12,14H2,1-4H3

> <INCHI_KEY>
WNKDGPXNFMMOEJ-UHFFFAOYNA-N

> <FORMULA>
C23H30N2O4

> <MOLECULAR_WEIGHT>
398.503

> <EXACT_MASS>
398.220557454

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
43.56619466054381

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,13-tetraene-10-carboxylate

> <JCHEM_LOGP>
2.360508191

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.7596375727156

> <JCHEM_PKA_STRONGEST_BASIC>
8.81513799840542

> <JCHEM_POLAR_SURFACE_AREA>
62.24000000000001

> <JCHEM_REFRACTIVITY>
111.93909999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl 12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,13-tetraene-10-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

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       0.276   0.401   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.714   0.951   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.910  -0.019   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.152   1.502   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.591   2.052   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.799   3.373   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.786   1.082   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       7.308   1.321   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       8.008   2.692   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.005  -0.052   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.493  -0.452   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.890  -1.940   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.377  -2.340   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.467  -1.253   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.799  -3.028   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.312  -2.628   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.915  -1.140   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.544  -0.439   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.512  -1.637   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.672  -2.928   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       3.863  -2.510   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       2.425  -3.061   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.229  -2.090   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.472  -0.570   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.106  -0.990   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.754   3.061   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.210   2.558   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       5.462   4.573   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.625   5.582   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24   25                                             
CONECT    4    3    5                                                       
CONECT    5    4    6    7   26                                             
CONECT    6    5                                                            
CONECT    7    5    8   18                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   10   18                                                  
CONECT   18   17    7   19   25                                             
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    3                                                       
CONECT   25   21    3   18                                                  
CONECT   26    5   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₀N₂O₄

Average Mass

398.5030 Da

Monoisotopic Mass

398.22056 Da

IUPAC Name

methyl 12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,13-tetraene-10-carboxylate

Traditional Name

methyl 12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,13-tetraene-10-carboxylate

CAS Registry Number

Not Available

SMILES

CCC12CC(O)(C3N(C)C4=CC(OC)=CC=C4C33CCN(CC=C1)C23)C(=O)OC

InChI Identifier

InChI=1/C23H30N2O4/c1-5-21-9-6-11-25-12-10-22(18(21)25)16-8-7-15(28-3)13-17(16)24(2)19(22)23(27,14-21)20(26)29-4/h6-9,13,18-19,27H,5,10-12,14H2,1-4H3

InChI Key

WNKDGPXNFMMOEJ-UHFFFAOYNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Classification

Not classified

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	2.36	ChemAxon
pKa (Strongest Acidic)	11.76	ChemAxon
pKa (Strongest Basic)	8.82	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	62.24 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	111.94 m³·mol⁻¹	ChemAxon
Polarizability	43.57 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

Desacetoxyvindoline

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tang W, Liu X, He Y, Yang F: Enhancement of Vindoline and Catharanthine Accumulation, Antioxidant Enzymes Activities, and Gene Expression Levels in Catharanthus roseus Leaves by Chitooligosaccharides Elicitation. Mar Drugs. 2022 Mar 3;20(3). pii: md20030188. doi: 10.3390/md20030188. [PubMed:35323487 ]
Sears JE, Boger DL: Tandem Intramolecular Diels-Alder/1,3-Dipolar Cycloaddition Cascade of 1,3,4-Oxadiazoles: Initial Scope and Applications. Acc Chem Res. 2016 Feb 16;49(2):241-51. doi: 10.1021/acs.accounts.5b00510. Epub 2016 Jan 27. [PubMed:26813287 ]
Guirimand G, Guihur A, Poutrain P, Hericourt F, Mahroug S, St-Pierre B, Burlat V, Courdavault V: Spatial organization of the vindoline biosynthetic pathway in Catharanthus roseus. J Plant Physiol. 2011 Apr 15;168(6):549-57. doi: 10.1016/j.jplph.2010.08.018. Epub 2010 Nov 2. [PubMed:21047699 ]
Boon BA, Yu YY, Boger DL: Total synthesis of (-)-4-desacetoxy-1-oxovindoline: Single atom exchange of an embedded core heteroatom in vindoline. Tetrahedron. 2021 May 7;87:132117. doi: 10.1016/j.tet.2021.132117. Epub 2021 Mar 29. [PubMed:33994597 ]
Soltani N, Nazarian-Firouzabadi F, Shafeinia A, Sadr AS, Shirali M: The expression of Terpenoid Indole Alkaloid (TIAs) pathway genes in Catharanthus roseus in response to salicylic acid treatment. Mol Biol Rep. 2020 Sep;47(9):7009-7016. doi: 10.1007/s11033-020-05759-y. Epub 2020 Sep 4. [PubMed:32886329 ]
Pengfei Z, Jianhua Z, Rongmin Y, Jiachen Z: Enzyme Inhibitors Cause Multiple Effects on Accumulation of Monoterpene Indole Alkaloids in Catharanthus Roseus Cambial Meristematic Cell Cultures. Pharmacogn Mag. 2017 Oct-Dec;13(52):732-737. doi: 10.4103/0973-1296.218121. Epub 2017 Nov 13. [PubMed:29200741 ]
Wang M, Zi J, Zhu J, Chen S, Wang P, Song L, Yu R: Artemisinic Acid Serves as a Novel ORCA3 Inducer to Enhance Biosynthesis of Terpenoid Indole Alkaloids in Catharanthus roseus Cambial Meristematic Cells. Nat Prod Commun. 2016 Jun;11(6):715-7. [PubMed:27534099 ]
Pandey SS, Singh S, Babu CS, Shanker K, Srivastava NK, Shukla AK, Kalra A: Fungal endophytes of Catharanthus roseus enhance vindoline content by modulating structural and regulatory genes related to terpenoid indole alkaloid biosynthesis. Sci Rep. 2016 May 25;6:26583. doi: 10.1038/srep26583. [PubMed:27220774 ]
Zhou C, Zhang J, Zhao SJ, Hu ZB: An active Catharanthus roseus desacetoxyvindoline-4-hydroxylase-like gene and its transcriptional regulatory profile. Bot Stud. 2014 Dec;55(1):29. doi: 10.1186/1999-3110-55-29. Epub 2014 Mar 13. [PubMed:28510984 ]
Ishikawa H, Elliott GI, Velcicky J, Choi Y, Boger DL: Total synthesis of (-)- and ent-(+)-vindoline and related alkaloids. J Am Chem Soc. 2006 Aug 16;128(32):10596-612. doi: 10.1021/ja061256t. [PubMed:16895428 ]

Showing NP-Card for desacetoxyvindoline (NP0339592)

MOL for NP0339592 (desacetoxyvindoline)

3D MOL for NP0339592 (desacetoxyvindoline)

3D SDF for NP0339592 (desacetoxyvindoline)

3D-SDF for NP0339592 (desacetoxyvindoline)

PDB for NP0339592 (desacetoxyvindoline)

3D PDB for NP0339592 (desacetoxyvindoline)

SMILES for NP0339592 (desacetoxyvindoline)

INCHI for NP0339592 (desacetoxyvindoline)

Structure for NP0339592 (desacetoxyvindoline)

3D Structure for NP0339592 (desacetoxyvindoline)