NP-MRD: Showing NP-Card for 25-Acetoxyluffariellin A (NP0076029)

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Record Information

Version

2.0

Created at

2022-04-28 21:13:07 UTC

Updated at

2022-04-28 21:13:07 UTC

NP-MRD ID

NP0076029

Secondary Accession Numbers

None

Natural Product Identification

Common Name

25-Acetoxyluffariellin A

Description

(2R)-3-[(2R,6S)-6-hydroxy-5-[(3E)-4-methyl-6-[(1R,2R)-2-methyl-1-(prop-1-en-2-yl)cyclopentyl]hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl]-5-oxo-2,5-dihydrofuran-2-yl acetate belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. 25-Acetoxyluffariellin A is found in Luffariella variabilis. Based on a literature review very few articles have been published on (2R)-3-[(2R,6S)-6-hydroxy-5-[(3E)-4-methyl-6-[(1R,2R)-2-methyl-1-(prop-1-en-2-yl)cyclopentyl]hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl]-5-oxo-2,5-dihydrofuran-2-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223132D          

 33 35  0  0  1  0            999 V2000
    0.7145    5.9411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.2911    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    4.7036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    5.5286    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    5.9411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1270    2.1965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3020    2.1965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1353    2.9390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4289    7.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6864   11.2855    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4008   11.6980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0139   11.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6784   10.3923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579    8.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
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  8 13  1  0  0  0  0
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  1 18  1  0  0  0  0
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 21 33  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282223132D          

 33 35  0  0  1  0            999 V2000
    0.7145    5.9411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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M  END
> <DATABASE_ID>
NP0076029

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CCC[C@]1(CC\C(C)=C\CCC1=CC[C@@H](O[C@@H]1O)C1=CC(=O)O[C@H]1OC(C)=O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O6/c1-17(2)27(14-7-9-19(27)4)15-13-18(3)8-6-10-21-11-12-23(32-25(21)30)22-16-24(29)33-26(22)31-20(5)28/h8,11,16,19,23,25-26,30H,1,6-7,9-10,12-15H2,2-5H3/b18-8+/t19-,23-,25+,26-,27+/m1/s1

> <INCHI_KEY>
XHZRTBPTEWIFSK-OISDGEQOSA-N

> <FORMULA>
C27H38O6

> <MOLECULAR_WEIGHT>
458.595

> <EXACT_MASS>
458.266838944

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
51.85636806497107

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-3-[(2R,6S)-6-hydroxy-5-[(3E)-4-methyl-6-[(1R,2R)-2-methyl-1-(prop-1-en-2-yl)cyclopentyl]hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl]-5-oxo-2,5-dihydrofuran-2-yl acetate

> <ALOGPS_LOGP>
4.44

> <JCHEM_LOGP>
5.479348971333334

> <ALOGPS_LOGS>
-5.09

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.841402053533896

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7695762081970772

> <JCHEM_PKA_STRONGEST_BASIC>
-4.181379183673136

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
127.82819999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.74e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-3-[(2R,6S)-6-hydroxy-5-[(3E)-4-methyl-6-[(1R,2R)-2-methyl-1-(prop-1-en-2-yl)cyclopentyl]hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl]-5-oxo-2H-furan-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.334  11.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  10.320   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   8.780   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   8.010   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000   8.780   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.000  10.320   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.334  11.090   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334   6.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.580   5.565   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.104   4.100   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.009   2.854   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.564   4.100   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.088   5.565   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.377   6.041   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.521   5.010   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.986   5.486   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.201   3.504   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  12.630   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  13.400   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  14.940   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  15.710   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  17.250   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335  18.020   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335  19.560   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.015  21.066   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.348  21.836   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.493  20.806   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.866  19.399   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.608  21.693   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.803  19.399   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.898  20.645   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.177  17.992   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.335  14.940   0.000  0.00  0.00           C+0
CONECT    1    2    6   18                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    4    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    1   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   33                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   28   30                                             
CONECT   25   24   26   29                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   24                                                       
CONECT   29   25                                                            
CONECT   30   24   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   21                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
(2R)-3-[(2R,6S)-6-Hydroxy-5-[(3E)-4-methyl-6-[(1R,2R)-2-methyl-1-(prop-1-en-2-yl)cyclopentyl]hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl]-5-oxo-2,5-dihydrofuran-2-yl acetic acid	Generator

Chemical Formula

C₂₇H₃₈O₆

Average Mass

458.5950 Da

Monoisotopic Mass

458.26684 Da

IUPAC Name

(2R)-3-[(2R,6S)-6-hydroxy-5-[(3E)-4-methyl-6-[(1R,2R)-2-methyl-1-(prop-1-en-2-yl)cyclopentyl]hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl]-5-oxo-2,5-dihydrofuran-2-yl acetate

Traditional Name

(2R)-3-[(2R,6S)-6-hydroxy-5-[(3E)-4-methyl-6-[(1R,2R)-2-methyl-1-(prop-1-en-2-yl)cyclopentyl]hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl]-5-oxo-2H-furan-2-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1CCC[C@]1(CC\C(C)=C\CCC1=CC[C@@H](O[C@@H]1O)C1=CC(=O)O[C@H]1OC(C)=O)C(C)=C

InChI Identifier

InChI=1S/C27H38O6/c1-17(2)27(14-7-9-19(27)4)15-13-18(3)8-6-10-21-11-12-23(32-25(21)30)22-16-24(29)33-26(22)31-20(5)28/h8,11,16,19,23,25-26,30H,1,6-7,9-10,12-15H2,2-5H3/b18-8+/t19-,23-,25+,26-,27+/m1/s1

InChI Key

XHZRTBPTEWIFSK-OISDGEQOSA-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
Luffariella variabilis	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Monoterpenoid
Monocyclic monoterpenoid
11-noriridane monoterpenoid
Acylal
Pyran
Dicarboxylic acid or derivatives
2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Dihydrofuran
Lactone
Hemiacetal
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	4.44	ALOGPS
logP	5.48	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	1.77	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	127.83 m³·mol⁻¹	ChemAxon
Polarizability	51.86 Å³	ChemAxon
Number of Rings	3	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

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

162917749

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 25-Acetoxyluffariellin A (NP0076029)

MOL for NP0076029 (25-Acetoxyluffariellin A)

3D MOL for NP0076029 (25-Acetoxyluffariellin A)

3D SDF for NP0076029 (25-Acetoxyluffariellin A)

3D-SDF for NP0076029 (25-Acetoxyluffariellin A)

PDB for NP0076029 (25-Acetoxyluffariellin A)

3D PDB for NP0076029 (25-Acetoxyluffariellin A)

SMILES for NP0076029 (25-Acetoxyluffariellin A)

INCHI for NP0076029 (25-Acetoxyluffariellin A)

Structure for NP0076029 (25-Acetoxyluffariellin A)

3D Structure for NP0076029 (25-Acetoxyluffariellin A)