NP-MRD: Showing NP-Card for 3-propyl-6-[(2r,3s,4e,7e,10e,12e,15r,16r,17s,18e)-3,15,17-trihydroxy-4,8,10,12,16,18-hexamethylicosa-4,7,10,12,18-pentaen-2-yl]pyran-2-one (NP0210362)

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Record Information

Version

2.0

Created at

2022-09-05 08:08:14 UTC

Updated at

2022-09-05 08:08:14 UTC

NP-MRD ID

NP0210362

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-propyl-6-[(2r,3s,4e,7e,10e,12e,15r,16r,17s,18e)-3,15,17-trihydroxy-4,8,10,12,16,18-hexamethylicosa-4,7,10,12,18-pentaen-2-yl]pyran-2-one

Description

Lagunapyrone B belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 3-propyl-6-[(2r,3s,4e,7e,10e,12e,15r,16r,17s,18e)-3,15,17-trihydroxy-4,8,10,12,16,18-hexamethylicosa-4,7,10,12,18-pentaen-2-yl]pyran-2-one was first documented in 2006 (PMID: 17061905). Based on a literature review very few articles have been published on Lagunapyrone B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052210082D          

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M  END

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M  END


  Mrv1652309052210082D          

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    0.0000   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -9.4875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -8.6625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 O   0  0  0  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  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  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
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  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
 33 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 30 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0210362

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC1=CC=C(OC1=O)[C@H](C)[C@H](O)C(\C)=C\C\C=C(/C)C\C(C)=C\C(\C)=C\C[C@@H](O)[C@@H](C)[C@H](O)C(\C)=C\C

> <INCHI_IDENTIFIER>
InChI=1S/C34H52O5/c1-10-13-29-17-19-31(39-34(29)38)28(9)33(37)26(7)15-12-14-22(3)20-24(5)21-23(4)16-18-30(35)27(8)32(36)25(6)11-2/h11,14-17,19,21,27-28,30,32-33,35-37H,10,12-13,18,20H2,1-9H3/b22-14+,23-16+,24-21+,25-11+,26-15+/t27-,28+,30-,32-,33-/m1/s1

> <INCHI_KEY>
OTNYCNDIGKWKTO-KOJVWQQKSA-N

> <FORMULA>
C34H52O5

> <MOLECULAR_WEIGHT>
540.785

> <EXACT_MASS>
540.381474774

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
91

> <JCHEM_AVERAGE_POLARIZABILITY>
63.80713547759457

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-propyl-6-[(2R,3S,4E,7E,10E,12E,15R,16R,17S,18E)-3,15,17-trihydroxy-4,8,10,12,16,18-hexamethylicosa-4,7,10,12,18-pentaen-2-yl]-2H-pyran-2-one

> <JCHEM_LOGP>
6.684889255333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.442136127291093

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.903658069890536

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8830414426204145

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
168.65380000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-propyl-6-[(2R,3S,4E,7E,10E,12E,15R,16R,17S,18E)-3,15,17-trihydroxy-4,8,10,12,16,18-hexamethylicosa-4,7,10,12,18-pentaen-2-yl]pyran-2-one

> <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     -12.003 -16.170   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.669 -15.400   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.336 -16.170   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.336 -17.710   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.002 -15.400   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -8.002 -13.860   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -6.668 -16.170   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.668 -17.710   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335 -15.400   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -5.335 -13.860   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667 -15.400   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334 -17.710   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000 -15.400   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334 -17.710   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667 -15.400   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335 -15.400   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001 -17.710   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335 -18.480   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668 -17.710   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002 -18.480   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.002 -20.020   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.336 -17.710   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.669 -18.480   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       9.336 -16.170   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.002 -15.400   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.669 -15.400   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.003 -13.090   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.337 -13.860   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      14.670 -13.090   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      16.004 -13.860   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      17.338 -13.090   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      13.337 -15.400   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      14.670 -16.170   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      12.003 -16.170   0.000  0.00  0.00           O+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    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   39                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   37                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37   33   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   30                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₅₂O₅

Average Mass

540.7850 Da

Monoisotopic Mass

540.38147 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCCC1=CC=C(OC1=O)[C@H](C)[C@H](O)C(\C)=C\C\C=C(/C)C\C(C)=C\C(\C)=C\C[C@@H](O)[C@@H](C)[C@H](O)C(\C)=C\C

InChI Identifier

InChI=1S/C34H52O5/c1-10-13-29-17-19-31(39-34(29)38)28(9)33(37)26(7)15-12-14-22(3)20-24(5)21-23(4)16-18-30(35)27(8)32(36)25(6)11-2/h11,14-17,19,21,27-28,30,32-33,35-37H,10,12-13,18,20H2,1-9H3/b22-14+,23-16+,24-21+,25-11+,26-15+/t27-,28+,30-,32-,33-/m1/s1

InChI Key

OTNYCNDIGKWKTO-KOJVWQQKSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Long chain fatty alcohol
Fatty alcohol
Pyranone
Fatty acyl
Pyran
Heteroaromatic compound
Secondary alcohol
Lactone
Organoheterocyclic compound
Polyol
Oxacycle
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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

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

8612729

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10437305

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yang F, Newsome JJ, Curran DP: Structure assignment of lagunapyrone B by fluorous mixture synthesis of four candidate stereoisomers. J Am Chem Soc. 2006 Nov 1;128(43):14200-5. doi: 10.1021/ja064812s. [PubMed:17061905 ]
LOTUS database [Link]

Showing NP-Card for 3-propyl-6-[(2r,3s,4e,7e,10e,12e,15r,16r,17s,18e)-3,15,17-trihydroxy-4,8,10,12,16,18-hexamethylicosa-4,7,10,12,18-pentaen-2-yl]pyran-2-one (NP0210362)

MOL for NP0210362 (3-propyl-6-[(2r,3s,4e,7e,10e,12e,15r,16r,17s,18e)-3,15,17-trihydroxy-4,8,10,12,16,18-hexamethylicosa-4,7,10,12,18-pentaen-2-yl]pyran-2-one)

3D MOL for NP0210362 (3-propyl-6-[(2r,3s,4e,7e,10e,12e,15r,16r,17s,18e)-3,15,17-trihydroxy-4,8,10,12,16,18-hexamethylicosa-4,7,10,12,18-pentaen-2-yl]pyran-2-one)

3D SDF for NP0210362 (3-propyl-6-[(2r,3s,4e,7e,10e,12e,15r,16r,17s,18e)-3,15,17-trihydroxy-4,8,10,12,16,18-hexamethylicosa-4,7,10,12,18-pentaen-2-yl]pyran-2-one)

3D-SDF for NP0210362 (3-propyl-6-[(2r,3s,4e,7e,10e,12e,15r,16r,17s,18e)-3,15,17-trihydroxy-4,8,10,12,16,18-hexamethylicosa-4,7,10,12,18-pentaen-2-yl]pyran-2-one)

PDB for NP0210362 (3-propyl-6-[(2r,3s,4e,7e,10e,12e,15r,16r,17s,18e)-3,15,17-trihydroxy-4,8,10,12,16,18-hexamethylicosa-4,7,10,12,18-pentaen-2-yl]pyran-2-one)

3D PDB for NP0210362 (3-propyl-6-[(2r,3s,4e,7e,10e,12e,15r,16r,17s,18e)-3,15,17-trihydroxy-4,8,10,12,16,18-hexamethylicosa-4,7,10,12,18-pentaen-2-yl]pyran-2-one)

SMILES for NP0210362 (3-propyl-6-[(2r,3s,4e,7e,10e,12e,15r,16r,17s,18e)-3,15,17-trihydroxy-4,8,10,12,16,18-hexamethylicosa-4,7,10,12,18-pentaen-2-yl]pyran-2-one)

INCHI for NP0210362 (3-propyl-6-[(2r,3s,4e,7e,10e,12e,15r,16r,17s,18e)-3,15,17-trihydroxy-4,8,10,12,16,18-hexamethylicosa-4,7,10,12,18-pentaen-2-yl]pyran-2-one)

Structure for NP0210362 (3-propyl-6-[(2r,3s,4e,7e,10e,12e,15r,16r,17s,18e)-3,15,17-trihydroxy-4,8,10,12,16,18-hexamethylicosa-4,7,10,12,18-pentaen-2-yl]pyran-2-one)

3D Structure for NP0210362 (3-propyl-6-[(2r,3s,4e,7e,10e,12e,15r,16r,17s,18e)-3,15,17-trihydroxy-4,8,10,12,16,18-hexamethylicosa-4,7,10,12,18-pentaen-2-yl]pyran-2-one)