NP-MRD: Showing NP-Card for Chatenaytrienin 2 (NP0082152)

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Record Information

Version

2.0

Created at

2022-04-29 03:12:26 UTC

Updated at

2022-04-29 03:12:26 UTC

NP-MRD ID

NP0082152

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chatenaytrienin 2

Description

Chatenaytrienin-2 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 2 is found in Annona muricata . Chatenaytrienin 2 was first documented in 2019 (PMID: 31475519). Based on a literature review very few articles have been published on Chatenaytrienin-2.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652304292205122D          

 37 37  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END

  Mrv1652304292205122D          

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    1.7848    9.8432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0703    9.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0703    8.6057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558    8.1932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558    7.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0703    6.9557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7848    7.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4993    6.9557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4993    6.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2137    5.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9282    6.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6427    5.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3571    6.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0716    5.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7861    6.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5006    5.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2150    6.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9295    5.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6440    6.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3584    5.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0729    6.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7874    5.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2546   13.8427    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  2  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  1  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
  2 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0082152

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCC\C=C/CC\C=C/CC\C=C/CCCCCCCCC1=C[C@H](C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C35H60O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29-30-31-34-32-33(2)37-35(34)36/h14-15,18-19,22-23,32-33H,3-13,16-17,20-21,24-31H2,1-2H3/b15-14-,19-18-,23-22-/t33-/m0/s1

> <INCHI_KEY>
GTXRLWWQVRDMLK-NTMIIVPOSA-N

> <FORMULA>
C35H60O2

> <MOLECULAR_WEIGHT>
512.863

> <EXACT_MASS>
512.459331172

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
97

> <JCHEM_AVERAGE_POLARIZABILITY>
68.2746602438691

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S)-5-methyl-3-[(9Z,13Z,17Z)-triaconta-9,13,17-trien-1-yl]-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
10.61

> <JCHEM_LOGP>
13.155467417666669

> <ALOGPS_LOGS>
-7.83

> <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>
166.80210000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
26

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.64e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-5-methyl-3-[(9Z,13Z,17Z)-triaconta-9,13,17-trien-1-yl]-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       9.230  24.594   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.770  24.594   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.246  23.129   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.000  22.224   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.754  23.129   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.289  22.653   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.000  20.684   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.666  19.914   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.666  18.374   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.333  17.604   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.333  16.064   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.999  15.294   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.665  16.064   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.665  17.604   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.332  18.374   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.998  17.604   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.998  16.064   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.664  15.294   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.664  13.754   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.998  12.984   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.332  13.754   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.665  12.984   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.665  11.444   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.999  10.674   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.333  11.444   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.666  10.674   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.000  11.444   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.334  10.674   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.667  11.444   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.001  10.674   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      15.335  11.444   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      16.668  10.674   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      18.002  11.444   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      19.336  10.674   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      20.669  11.444   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      22.003  10.674   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      11.675  25.840   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3   37                                                  
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                                                            
CONECT   37    2                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₅H₆₀O₂

Average Mass

512.8630 Da

Monoisotopic Mass

512.45933 Da

IUPAC Name

(5S)-5-methyl-3-[(9Z,13Z,17Z)-triaconta-9,13,17-trien-1-yl]-2,5-dihydrofuran-2-one

Traditional Name

(5S)-5-methyl-3-[(9Z,13Z,17Z)-triaconta-9,13,17-trien-1-yl]-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCC\C=C/CC\C=C/CC\C=C/CCCCCCCCC1=C[C@H](C)OC1=O

InChI Identifier

InChI=1S/C35H60O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29-30-31-34-32-33(2)37-35(34)36/h14-15,18-19,22-23,32-33H,3-13,16-17,20-21,24-31H2,1-2H3/b15-14-,19-18-,23-22-/t33-/m0/s1

InChI Key

GTXRLWWQVRDMLK-NTMIIVPOSA-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	10.61	ALOGPS
logP	13.16	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	26	ChemAxon
Refractivity	166.8 m³·mol⁻¹	ChemAxon
Polarizability	68.27 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

103882801

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101949814

PDB ID

Not Available

ChEBI ID

188036

Good Scents ID

Not Available

References

General References

Kunkalkar RA, Fernandes RA: Protecting-Group-Free Total Synthesis of Chatenaytrienin-2. J Org Chem. 2019 Sep 20;84(18):12216-12220. doi: 10.1021/acs.joc.9b01952. Epub 2019 Sep 11. [PubMed:31475519 ]

Showing NP-Card for Chatenaytrienin 2 (NP0082152)

MOL for NP0082152 (Chatenaytrienin 2)

3D MOL for NP0082152 (Chatenaytrienin 2)

3D SDF for NP0082152 (Chatenaytrienin 2)

3D-SDF for NP0082152 (Chatenaytrienin 2)

PDB for NP0082152 (Chatenaytrienin 2)

3D PDB for NP0082152 (Chatenaytrienin 2)

SMILES for NP0082152 (Chatenaytrienin 2)

INCHI for NP0082152 (Chatenaytrienin 2)

Structure for NP0082152 (Chatenaytrienin 2)

3D Structure for NP0082152 (Chatenaytrienin 2)