NP-MRD: Showing NP-Card for Chatenaytrienin 4 (NP0082154)

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Record Information

Version

2.0

Created at

2022-04-29 03:12:33 UTC

Updated at

2022-04-29 03:12:33 UTC

NP-MRD ID

NP0082154

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chatenaytrienin 4

Description

Chatenaytrienin-4 belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. Chatenaytrienin 4 is found in Annona muricata . Based on a literature review very few articles have been published on Chatenaytrienin-4.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652304292205122D          

 39 39  0  0  1  0            999 V2000
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M  END

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M  END

  Mrv1652304292205122D          

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    0.2036    1.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7013    0.8588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2229    2.5762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8465    2.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6261    2.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2497    1.7660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0293    2.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6529    1.4960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4325    1.7660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0561    1.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8357    1.4960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4593    0.9559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2389    1.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3948    2.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7711    2.5762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9270    3.3863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7066    3.6564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3302    3.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1098    3.3863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2657    4.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6420    4.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7980    5.5467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5775    5.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7334    6.6268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1098    7.1669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2657    7.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6420    8.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7980    9.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1743    9.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3302   10.6775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7066   11.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8625   12.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2389   12.5678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3948   13.3780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6807    2.5201    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  2  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  2  0  0  0  0
  4  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
 10 11  1  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
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  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
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
  2 39  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0082154

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCC\C=C/CC\C=C/CC\C=C/CCCCCCCCCCCCC1=C[C@H](C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C37H64O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29-30-31-32-33-36-34-35(2)39-37(36)38/h12-13,16-17,20-21,34-35H,3-11,14-15,18-19,22-33H2,1-2H3/b13-12-,17-16-,21-20-/t35-/m0/s1

> <INCHI_KEY>
BOWRZSGIKPRYCT-YYYDTODKSA-N

> <FORMULA>
C37H64O2

> <MOLECULAR_WEIGHT>
540.917

> <EXACT_MASS>
540.490631301

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
103

> <JCHEM_AVERAGE_POLARIZABILITY>
72.52926635251386

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S)-3-[(13Z,17Z,21Z)-dotriaconta-13,17,21-trien-1-yl]-5-methyl-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
10.85

> <JCHEM_LOGP>
14.044604747666666

> <ALOGPS_LOGS>
-7.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.470827754881434

> <JCHEM_PKA_STRONGEST_BASIC>
-6.879887748924185

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
176.00410000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
28

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.74e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-3-[(13Z,17Z,21Z)-dotriaconta-13,17,21-trien-1-yl]-5-methyl-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0      -1.160   2.801   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.664   4.257   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.436   5.186   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.828   4.305   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.380   2.831   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.309   1.603   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.283   4.809   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.447   3.801   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.902   4.305   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.066   3.297   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.521   3.801   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.685   2.793   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.141   3.297   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.305   2.288   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.760   2.793   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.924   1.784   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.379   2.288   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.670   3.801   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.506   4.809   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.797   6.321   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.252   6.825   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.416   5.817   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.872   6.321   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.163   7.833   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.998   8.842   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.290  10.354   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      19.745  10.858   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      20.036  12.370   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      18.872  13.378   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      19.163  14.891   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      17.998  15.899   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      18.290  17.411   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      17.125  18.419   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      17.416  19.931   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      16.252  20.940   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      16.543  22.452   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      15.379  23.460   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      15.670  24.972   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -3.137   4.704   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3   39                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    1    6                                                  
CONECT    6    5                                                            
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37                                                            
CONECT   39    2                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₇H₆₄O₂

Average Mass

540.9170 Da

Monoisotopic Mass

540.49063 Da

IUPAC Name

(5S)-3-[(13Z,17Z,21Z)-dotriaconta-13,17,21-trien-1-yl]-5-methyl-2,5-dihydrofuran-2-one

Traditional Name

(5S)-3-[(13Z,17Z,21Z)-dotriaconta-13,17,21-trien-1-yl]-5-methyl-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

CCCCCCCCCC\C=C/CC\C=C/CC\C=C/CCCCCCCCCCCCC1=C[C@H](C)OC1=O

InChI Identifier

InChI=1S/C37H64O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29-30-31-32-33-36-34-35(2)39-37(36)38/h12-13,16-17,20-21,34-35H,3-11,14-15,18-19,22-33H2,1-2H3/b13-12-,17-16-,21-20-/t35-/m0/s1

InChI Key

BOWRZSGIKPRYCT-YYYDTODKSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Annona muricata	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous acetogenins

Alternative Parents

Substituents

Annonaceae acetogenin skeleton
2-furanone
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	10.85	ALOGPS
logP	14.04	ChemAxon
logS	-7.8	ALOGPS
pKa (Strongest Acidic)	13.47	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	28	ChemAxon
Refractivity	176 m³·mol⁻¹	ChemAxon
Polarizability	72.53 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

103882802

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101949816

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Chatenaytrienin 4 (NP0082154)

MOL for NP0082154 (Chatenaytrienin 4)

3D MOL for NP0082154 (Chatenaytrienin 4)

3D SDF for NP0082154 (Chatenaytrienin 4)

3D-SDF for NP0082154 (Chatenaytrienin 4)

PDB for NP0082154 (Chatenaytrienin 4)

3D PDB for NP0082154 (Chatenaytrienin 4)

SMILES for NP0082154 (Chatenaytrienin 4)

INCHI for NP0082154 (Chatenaytrienin 4)

Structure for NP0082154 (Chatenaytrienin 4)

3D Structure for NP0082154 (Chatenaytrienin 4)