NP-MRD: Showing NP-Card for Passifetilactone D (NP0333256)

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Record Information

Version

2.0

Created at

2024-05-16 09:04:01 UTC

Updated at

2025-12-20 10:41:06 UTC

NP-MRD ID

NP0333256

Natural Product DOI

https://doi.org/10.57994/2593

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Passifetilactone D

Description

Passifetilactone D belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. Passifetilactone D was first documented in 2024 (PMID: 38787359). Based on a literature review very few articles have been published on Passifetilactone D.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01282311402D          

 25 26  0  0  1  0            999 V2000
  -10.6914    0.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9770    1.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2625    0.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5480    1.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8336    0.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1191    1.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4046    0.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6901    1.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9757    0.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2612    1.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5467    0.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8323    1.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1178    0.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4033    1.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6889    0.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0256    1.2159    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6801    0.7136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4981    0.8213    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0003    1.4758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7257    1.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0821    2.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4202    2.6883    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2381    2.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8926    2.2938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6071    2.7063    0.0000 O   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
  6  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
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 18 17  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  6  0  0  0
 16 21  1  0  0  0  0
 22 21  1  0  0  0  0
 22 20  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333256

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCC[C@@H]1C[C@@H]2C[C@@H](CC(=O)O2)O1

> <INCHI_IDENTIFIER>
InChI=1S/C22H40O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-16-20-17-21(24-19)18-22(23)25-20/h19-21H,2-18H2,1H3/t19-,20-,21+/m1/s1

> <INCHI_KEY>
GRPNFHMXMHZHBP-NJYVYQBISA-N

> <FORMULA>
C22H40O3

> <MOLECULAR_WEIGHT>
352.559

> <EXACT_MASS>
352.297745148

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
45.33023290791201

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,5S,7R)-7-pentadecyl-2,6-dioxabicyclo[3.3.1]nonan-3-one

> <JCHEM_LOGP>
6.6003333316666675

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.170814438849823

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
102.45459999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5S,7R)-7-pentadecyl-2,6-dioxabicyclo[3.3.1]nonan-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-JAN-23         0                                  
HETATM    1  C   UNK     0     -19.957   1.500   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -18.624   2.270   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -17.290   1.500   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -15.956   2.270   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -14.623   1.500   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -13.289   2.270   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -11.955   1.500   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -10.622   2.270   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.288   1.500   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.954   2.270   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.621   1.500   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.287   2.270   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.953   1.500   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.620   2.270   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.286   1.500   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.048   2.270   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.270   1.332   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.796   1.533   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.734   2.755   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.355   3.024   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.153   3.796   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.784   5.018   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.311   5.219   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.533   4.282   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.867   5.052   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    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   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18   24                                                       
CONECT   20   18   22                                                       
CONECT   21   16   22                                                       
CONECT   22   21   20   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   19   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₄₀O₃

Average Mass

352.5590 Da

Monoisotopic Mass

352.29775 Da

IUPAC Name

(1R,5S,7R)-7-pentadecyl-2,6-dioxabicyclo[3.3.1]nonan-3-one

Traditional Name

(1R,5S,7R)-7-pentadecyl-2,6-dioxabicyclo[3.3.1]nonan-3-one

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCC[C@@H]1C[C@@H]2C[C@@H](CC(=O)O2)O1

InChI Identifier

InChI=1S/C22H40O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-16-20-17-21(24-19)18-22(23)25-20/h19-21H,2-18H2,1H3/t19-,20-,21+/m1/s1

InChI Key

GRPNFHMXMHZHBP-NJYVYQBISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	[email protected]	Khon Kaen University	Suphasit Nathabumroong	2024-05-16	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	[email protected]	Khon Kaen University	Suphasit Nathabumroong	2024-05-16	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	[email protected]	Khon Kaen University	Suphasit Nathabumroong	2024-05-16	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	[email protected]	Khon Kaen University	Suphasit Nathabumroong	2024-05-16	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	[email protected]	Khon Kaen University	Suphasit Nathabumroong	2024-05-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	[email protected]	Khon Kaen University	Suphasit Nathabumroong	2024-05-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)	[email protected]	Khon Kaen University	Suphasit Nathabumroong	2024-05-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400.135201058 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400.135201058, CDCl₃, simulated)	[email protected]	Khon Kaen University	Suphasit Nathabumroong	2024-05-16	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Neo-uvaria foetida		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohol esters

Direct Parent

Fatty alcohol esters

Alternative Parents

Substituents

Fatty alcohol ester
Delta_valerolactone
Fatty acid ester
Delta valerolactone
Oxane
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	6.6	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	102.45 m³·mol⁻¹	ChemAxon
Polarizability	45.33 Å³	ChemAxon
Number of Rings	2	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ponsuwan K, Nathabumroong S, Lekphrom R, Sorin S, Saengboonmee C, Senawong T, Tontapha S, Schevenels FT: Passifetilactones A-E, Fatty Acid Lactones from the Fruit and Flowers of Passiflora foetida with Cytotoxic Activity. J Nat Prod. 2024 Jun 28;87(6):1652-1659. doi: 10.1021/acs.jnatprod.4c00463. Epub 2024 May 24. [PubMed:38787359 ]
DOI: 10.1021/acs.jnatprod.4c00463
PMID: 38787359

Showing NP-Card for Passifetilactone D (NP0333256)

MOL for NP0333256 (Passifetilactone D)

3D MOL for NP0333256 (Passifetilactone D)

3D SDF for NP0333256 (Passifetilactone D)

3D-SDF for NP0333256 (Passifetilactone D)

PDB for NP0333256 (Passifetilactone D)

3D PDB for NP0333256 (Passifetilactone D)

SMILES for NP0333256 (Passifetilactone D)

INCHI for NP0333256 (Passifetilactone D)

Structure for NP0333256 (Passifetilactone D)

3D Structure for NP0333256 (Passifetilactone D)