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Showing NP-Card for 3-Ethoxyniveusin A (NP0336521)

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Record Information
Version2.0
Created at2024-09-11 06:39:54 UTC
Updated at2024-09-11 06:39:54 UTC
NP-MRD IDNP0336521
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Ethoxyniveusin A
Description3-Ethoxyniveusin A belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Based on a literature review very few articles have been published on 3-Ethoxyniveusin A.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0336521 (3-Ethoxyniveusin A)


  Mrv2104 05262309122D          

 30 32  0  0  0  0            999 V2000
    2.3512    3.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7281    4.3207    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3933    4.3207    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2593    3.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2593    2.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3512    2.7107    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6482    5.1052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4732    5.1052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1078    3.9082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0607    0.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3933    1.3722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6482    2.1568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4732    2.1568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7281    1.3722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0607    0.0623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5128    1.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4514    4.7176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3214    4.7328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0296    3.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6705    3.3705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2171    1.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5025    1.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5025    2.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2170    2.7248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7881    2.7248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7881    3.5498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0736    2.3123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9581    5.7726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3219    5.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0366    5.9699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  6  1  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5 12  1  0  0  0  0
 13  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  2  1  0  0  0  0
  3  9  1  1  0  0  0
  2  9  1  1  0  0  0
 10 11  1  0  0  0  0
 10 14  1  0  0  0  0
 13 14  1  1  0  0  0
 12 13  1  0  0  0  0
 10 15  2  0  0  0  0
 14 16  2  0  0  0  0
  6 27  1  1  0  0  0
  2 17  1  6  0  0  0
  3 18  1  6  0  0  0
  4 19  1  0  0  0  0
 19 20  1  0  0  0  0
 12 11  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
  8 28  1  6  0  0  0
 18 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
Download

3D MOL for NP0336521 (3-Ethoxyniveusin A)

Download
3D SDF for NP0336521 (3-Ethoxyniveusin A)

  Mrv2104 05262309122D          

 30 32  0  0  0  0            999 V2000
    2.3512    3.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7281    4.3207    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3933    4.3207    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2593    3.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2593    2.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3512    2.7107    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6482    5.1052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4732    5.1052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1078    3.9082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0607    0.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3933    1.3722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6482    2.1568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4732    2.1568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7281    1.3722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0607    0.0623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5128    1.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4514    4.7176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3214    4.7328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0296    3.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6705    3.3705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2171    1.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5025    1.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5025    2.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2170    2.7248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7881    2.7248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7881    3.5498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0736    2.3123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9581    5.7726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3219    5.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0366    5.9699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  6  1  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5 12  1  0  0  0  0
 13  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  2  1  0  0  0  0
  3  9  1  1  0  0  0
  2  9  1  1  0  0  0
 10 11  1  0  0  0  0
 10 14  1  0  0  0  0
 13 14  1  1  0  0  0
 12 13  1  0  0  0  0
 10 15  2  0  0  0  0
 14 16  2  0  0  0  0
  6 27  1  1  0  0  0
  2 17  1  6  0  0  0
  3 18  1  6  0  0  0
  4 19  1  0  0  0  0
 19 20  1  0  0  0  0
 12 11  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
  8 28  1  6  0  0  0
 18 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336521

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCO[C@@]12C[C@H](O)[C@@](C)(C[C@@H](OC(=O)C(\C)=C\C)[C@@H]3[C@@H](CC1CO)OC(=O)C3=C)O2

> <INCHI_IDENTIFIER>
InChI=1/C22H32O8/c1-6-12(3)19(25)29-16-9-21(5)17(24)10-22(30-21,27-7-2)14(11-23)8-15-18(16)13(4)20(26)28-15/h6,14-18,23-24H,4,7-11H2,1-3,5H3/b12-6+/t14?,15-,16-,17+,18+,21?,22?/s2

> <INCHI_KEY>
CQMHDUOGTKOQML-CGCAYHLENA-N

> <FORMULA>
C22H32O8

> <MOLECULAR_WEIGHT>
424.49

> <EXACT_MASS>
424.20971799

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
44.23755282962465

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4R,8S,9R,11R,12S)-1-ethoxy-12-hydroxy-2-(hydroxymethyl)-11-methyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradecan-9-yl (2E)-2-methylbut-2-enoate

> <JCHEM_LOGP>
2.3091233853333337

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.31167411767918

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.802913926877466

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6687476422074523

> <JCHEM_POLAR_SURFACE_AREA>
111.52000000000001

> <JCHEM_REFRACTIVITY>
107.0933

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4R,8S,9R,11R,12S)-1-ethoxy-12-hydroxy-2-(hydroxymethyl)-11-methyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradecan-9-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0336521 (3-Ethoxyniveusin A)
Download
PDB for NP0336521 (3-Ethoxyniveusin A)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0       4.389   6.655   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.226   8.065   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.734   8.065   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.484   6.710   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.484   5.115   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.389   5.060   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.210   9.530   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.750   9.530   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.068   7.295   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.980   1.656   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.734   2.561   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.210   4.026   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.750   4.026   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.226   2.561   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.980   0.116   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.691   2.086   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.576   8.806   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.600   8.835   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.922   7.261   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -3.118   6.292   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.739   2.006   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.405   2.776   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.405   4.316   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.738   5.086   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.071   5.086   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.071   6.626   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       5.737   4.316   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       3.655  10.776   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.601  10.375   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.935  11.144   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    8    9   17                                             
CONECT    3    4    7    9   18                                             
CONECT    4    3    5   19                                                  
CONECT    5    4   12                                                       
CONECT    6    1   13   27                                                  
CONECT    7    3    8                                                       
CONECT    8    7    2   28                                                  
CONECT    9    3    2                                                       
CONECT   10   11   14   15                                                  
CONECT   11   10   12                                                       
CONECT   12    5   13   11                                                  
CONECT   13    6   14   12                                                  
CONECT   14   10   13   16                                                  
CONECT   15   10                                                            
CONECT   16   14                                                            
CONECT   17    2                                                            
CONECT   18    3   29                                                       
CONECT   19    4   20                                                       
CONECT   20   19                                                            
CONECT   21   22                                                            
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27    6   25                                                       
CONECT   28    8                                                            
CONECT   29   18   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

Download
3D PDB for NP0336521 (3-Ethoxyniveusin A)
Download
SMILES for NP0336521 (3-Ethoxyniveusin A)
CCO[C@@]12C[C@H](O)[C@@](C)(C[C@@H](OC(=O)C(\C)=C\C)[C@@H]3[C@@H](CC1CO)OC(=O)C3=C)O2
Download
INCHI for NP0336521 (3-Ethoxyniveusin A)
InChI=1/C22H32O8/c1-6-12(3)19(25)29-16-9-21(5)17(24)10-22(30-21,27-7-2)14(11-23)8-15-18(16)13(4)20(26)28-15/h6,14-18,23-24H,4,7-11H2,1-3,5H3/b12-6+/t14?,15-,16-,17+,18+,21?,22?/s2
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View in JSmol
SynonymsNot Available
Chemical FormulaC22H32O8
Average Mass424.4900 Da
Monoisotopic Mass424.20972 Da
IUPAC Name(1R,4R,8S,9R,11R,12S)-1-ethoxy-12-hydroxy-2-(hydroxymethyl)-11-methyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradecan-9-yl (2E)-2-methylbut-2-enoate
Traditional Name(1R,4R,8S,9R,11R,12S)-1-ethoxy-12-hydroxy-2-(hydroxymethyl)-11-methyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradecan-9-yl (2E)-2-methylbut-2-enoate
CAS Registry NumberNot Available
SMILES
CCO[C@@]12C[C@H](O)[C@@](C)(C[C@@H](OC(=O)C(\C)=C\C)[C@@H]3[C@@H](CC1CO)OC(=O)C3=C)O2
InChI Identifier
InChI=1/C22H32O8/c1-6-12(3)19(25)29-16-9-21(5)17(24)10-22(30-21,27-7-2)14(11-23)8-15-18(16)13(4)20(26)28-15/h6,14-18,23-24H,4,7-11H2,1-3,5H3/b12-6+/t14?,15-,16-,17+,18+,21?,22?/s2
InChI KeyCQMHDUOGTKOQML-CGCAYHLENA-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 germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassTerpene lactones  
Direct ParentGermacranolides and derivatives  
Alternative Parents
Substituents
  • Germacranolide
    • 

  • Sesquiterpenoid
    • 

  • Ketal
    • 

  • Fatty acid ester
    • 

  • Fatty acyl
    • 

  • Monosaccharide
    • 

  • Gamma butyrolactone
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Tetrahydrofuran
    • 

  • Secondary alcohol
    • 

  • Lactone
    • 

  • Carboxylic acid ester
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Carboxylic acid derivative
    • 

  • Acetal
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
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
logP2.31ChemAxon
pKa (Strongest Acidic)13.8ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area111.52 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity107.09 m³·mol⁻¹ChemAxon
Polarizability44.24 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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 ReferencesNot Available