NP-MRD: Showing NP-Card for (1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17-(acetyloxy)-8-(furan-3-yl)-4,12-dihydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-19-yl (2e)-2-methylbut-2-enoate (NP0206573)

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Record Information

Version

2.0

Created at

2022-09-05 02:52:19 UTC

Updated at

2022-09-05 02:52:20 UTC

NP-MRD ID

NP0206573

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17-(acetyloxy)-8-(furan-3-yl)-4,12-dihydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-19-yl (2e)-2-methylbut-2-enoate

Description

Volkensin belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. (1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17-(acetyloxy)-8-(furan-3-yl)-4,12-dihydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-19-yl (2e)-2-methylbut-2-enoate is found in Melia volkensii. (1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17-(acetyloxy)-8-(furan-3-yl)-4,12-dihydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-19-yl (2e)-2-methylbut-2-enoate was first documented in 2016 (PMID: 26862439). Based on a literature review a small amount of articles have been published on volkensin (PMID: 33499082) (PMID: 32825611) (PMID: 31979199).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052204522D          

 42 47  0  0  1  0            999 V2000
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 42 19  1  6  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309052204522D          

 42 47  0  0  1  0            999 V2000
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    0.3182   -2.1042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7422   -1.9855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6736   -1.1633    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9274   -0.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8588    0.0105    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1126    0.3623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5652   -0.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4966   -0.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3114    0.2435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5366    0.4810    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8311    0.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6405    1.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4509    1.4535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8479    0.7303    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6510    0.5414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2162    1.1425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8890   -0.2485    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4076    0.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7113   -0.3156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2202    0.3337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9941    1.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9950    0.0503    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6797    0.5106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7098    1.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5032    1.5611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9635    0.8765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4545    0.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9649   -0.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1715   -1.0003    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9232   -1.7870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1532   -2.0833    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0862   -2.9056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4415   -1.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3239   -0.8496    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3514   -0.6929    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5343   -1.4974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2828    0.1293    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 28 32  2  0  0  0  0
 27 33  1  0  0  0  0
 34 33  1  6  0  0  0
 24 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
 39 38  1  6  0  0  0
 22 39  1  0  0  0  0
 39 40  1  0  0  0  0
  8 40  1  0  0  0  0
 40 41  1  6  0  0  0
 40 42  1  0  0  0  0
 42 19  1  6  0  0  0
 15 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0206573

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/C)C(=O)O[C@H]1C[C@@H](OC(C)=O)[C@@]2(C)CO[C@@H]3[C@@H]2[C@@]1(C)[C@H]1C[C@H](O)O[C@H]2C[C@H](C(C)=C2[C@]1(C)[C@@H]3O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C33H44O9/c1-8-16(2)30(37)42-24-13-23(40-18(4)34)31(5)15-39-27-28(31)32(24,6)22-12-25(35)41-21-11-20(19-9-10-38-14-19)17(3)26(21)33(22,7)29(27)36/h8-10,14,20-25,27-29,35-36H,11-13,15H2,1-7H3/b16-8+/t20-,21+,22-,23-,24+,25-,27-,28+,29-,31-,32+,33-/m1/s1

> <INCHI_KEY>
KQNNSYZQMSOOQH-GLDAUDTLSA-N

> <FORMULA>
C33H44O9

> <MOLECULAR_WEIGHT>
584.706

> <EXACT_MASS>
584.298532997

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
62.52527480697671

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4R,6S,8R,11R,12S,13R,16R,17R,19S,20R)-17-(acetyloxy)-8-(furan-3-yl)-4,12-dihydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0^{2,11}.0^{6,10}.0^{16,20}]icos-9-en-19-yl (2E)-2-methylbut-2-enoate

> <JCHEM_LOGP>
3.102584949999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.69840058793389

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.422598713575827

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8439553110654403

> <JCHEM_POLAR_SURFACE_AREA>
124.66000000000001

> <JCHEM_REFRACTIVITY>
152.72120000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4R,6S,8R,11R,12S,13R,16R,17R,19S,20R)-17-(acetyloxy)-8-(furan-3-yl)-4,12-dihydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0^{2,11}.0^{6,10}.0^{16,20}]icos-9-en-19-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       0.978  -8.532   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.850  -6.997   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.115  -6.119   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.508  -6.776   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.987  -4.584   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.594  -3.928   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.252  -3.706   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.124  -2.172   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.731  -1.515   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.603   0.020   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.210   0.676   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.055  -0.202   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.927  -1.737   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.448   0.455   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.868   0.898   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.551   1.696   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.062   2.426   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.575   2.713   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.316   1.363   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.815   1.011   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.870   2.133   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.259  -0.464   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.228   0.734   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.794  -0.589   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.744   0.623   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.322   2.104   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.191   0.094   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.469   0.953   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.525   2.492   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.006   2.914   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      14.865   1.636   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      13.915   0.424   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.135  -1.445   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.654  -1.867   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       9.190  -3.336   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       7.753  -3.889   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       7.627  -5.424   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       6.424  -3.110   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.205  -1.586   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.389  -1.293   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       4.731  -2.795   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       4.261   0.241   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   40                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   10   16   17   42                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   42                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24   39                                             
CONECT   23   22                                                            
CONECT   24   22   25   34                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   33                                                  
CONECT   28   27   29   32                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   28                                                       
CONECT   33   27   34                                                       
CONECT   34   33   24   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   22   40                                                  
CONECT   40   39    8   41   42                                             
CONECT   41   40                                                            
CONECT   42   40   19   15                                                  
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Value	Source
RIP protein, a volkensii harms	MeSH
Ribosome-inactivating protein type 2, adenia volkensii	MeSH

Chemical Formula

C₃₃H₄₄O₉

Average Mass

584.7060 Da

Monoisotopic Mass

584.29853 Da

IUPAC Name

(1R,2R,4R,6S,8R,11R,12S,13R,16R,17R,19S,20R)-17-(acetyloxy)-8-(furan-3-yl)-4,12-dihydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0^{2,11}.0^{6,10}.0^{16,20}]icos-9-en-19-yl (2E)-2-methylbut-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

C\C=C(/C)C(=O)O[C@H]1C[C@@H](OC(C)=O)[C@@]2(C)CO[C@@H]3[C@@H]2[C@@]1(C)[C@H]1C[C@H](O)O[C@H]2C[C@H](C(C)=C2[C@]1(C)[C@@H]3O)C1=COC=C1

InChI Identifier

InChI=1S/C33H44O9/c1-8-16(2)30(37)42-24-13-23(40-18(4)34)31(5)15-39-27-28(31)32(24,6)22-12-25(35)41-21-11-20(19-9-10-38-14-19)17(3)26(21)33(22,7)29(27)36/h8-10,14,20-25,27-29,35-36H,11-13,15H2,1-7H3/b16-8+/t20-,21+,22-,23-,24+,25-,27-,28+,29-,31-,32+,33-/m1/s1

InChI Key

KQNNSYZQMSOOQH-GLDAUDTLSA-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
Melia volkensii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
Oxepane
Fatty acid ester
Fatty acyl
Dicarboxylic acid or derivatives
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Furan
Cyclic alcohol
Secondary alcohol
Hemiacetal
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	3.1	ChemAxon
pKa (Strongest Acidic)	12.42	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	124.66 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	152.72 m³·mol⁻¹	ChemAxon
Polarizability	62.53 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00027096

Chemspider ID

4942821

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Volkensin

METLIN ID

Not Available

PubChem Compound

6438338

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bortolotti M, Maiello S, Ferreras JM, Iglesias R, Polito L, Bolognesi A: Kirkiin: A New Toxic Type 2 Ribosome-Inactivating Protein from the Caudex of Adenia kirkii. Toxins (Basel). 2021 Jan 22;13(2):81. doi: 10.3390/toxins13020081. [PubMed:33499082 ]
Iglesias R, Polito L, Bortolotti M, Pedrazzi M, Citores L, Ferreras JM, Bolognesi A: Primary Sequence and 3D Structure Prediction of the Plant Toxin Stenodactylin. Toxins (Basel). 2020 Aug 21;12(9):538. doi: 10.3390/toxins12090538. [PubMed:32825611 ]
Jaoko V, Nji Tizi Taning C, Backx S, Mulatya J, Van den Abeele J, Magomere T, Olubayo F, Mangelinckx S, Werbrouck SPO, Smagghe G: The Phytochemical Composition of Melia volkensii and Its Potential for Insect Pest Management. Plants (Basel). 2020 Jan 22;9(2):143. doi: 10.3390/plants9020143. [PubMed:31979199 ]
Gulino R: Neuroplasticity and Repair in Rodent Neurotoxic Models of Spinal Motoneuron Disease. Neural Plast. 2016;2016:2769735. doi: 10.1155/2016/2769735. Epub 2016 Jan 3. [PubMed:26862439 ]
LOTUS database [Link]

Showing NP-Card for (1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17-(acetyloxy)-8-(furan-3-yl)-4,12-dihydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-19-yl (2e)-2-methylbut-2-enoate (NP0206573)

MOL for NP0206573 ((1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17-(acetyloxy)-8-(furan-3-yl)-4,12-dihydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-19-yl (2e)-2-methylbut-2-enoate)

3D MOL for NP0206573 ((1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17-(acetyloxy)-8-(furan-3-yl)-4,12-dihydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-19-yl (2e)-2-methylbut-2-enoate)

3D SDF for NP0206573 ((1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17-(acetyloxy)-8-(furan-3-yl)-4,12-dihydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-19-yl (2e)-2-methylbut-2-enoate)

3D-SDF for NP0206573 ((1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17-(acetyloxy)-8-(furan-3-yl)-4,12-dihydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-19-yl (2e)-2-methylbut-2-enoate)

PDB for NP0206573 ((1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17-(acetyloxy)-8-(furan-3-yl)-4,12-dihydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-19-yl (2e)-2-methylbut-2-enoate)

3D PDB for NP0206573 ((1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17-(acetyloxy)-8-(furan-3-yl)-4,12-dihydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-19-yl (2e)-2-methylbut-2-enoate)

SMILES for NP0206573 ((1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17-(acetyloxy)-8-(furan-3-yl)-4,12-dihydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-19-yl (2e)-2-methylbut-2-enoate)

INCHI for NP0206573 ((1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17-(acetyloxy)-8-(furan-3-yl)-4,12-dihydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-19-yl (2e)-2-methylbut-2-enoate)

Structure for NP0206573 ((1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17-(acetyloxy)-8-(furan-3-yl)-4,12-dihydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-19-yl (2e)-2-methylbut-2-enoate)

3D Structure for NP0206573 ((1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17-(acetyloxy)-8-(furan-3-yl)-4,12-dihydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-19-yl (2e)-2-methylbut-2-enoate)