NP-MRD: Showing NP-Card for (3e,6s)-6-[(2r,5s)-5-[(2r,2's,5r,5'r)-5'-[(2s,4e)-6-hydroxy-6-methylhept-4-en-2-yl]-[2,2'-bioxolan]-5-yl]oxolan-2-yl]-2-methylhept-3-en-2-ol (NP0182843)

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Record Information

Version

2.0

Created at

2022-09-03 21:39:05 UTC

Updated at

2022-09-03 21:39:05 UTC

NP-MRD ID

NP0182843

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3e,6s)-6-[(2r,5s)-5-[(2r,2's,5r,5'r)-5'-[(2s,4e)-6-hydroxy-6-methylhept-4-en-2-yl]-[2,2'-bioxolan]-5-yl]oxolan-2-yl]-2-methylhept-3-en-2-ol

Description

Longilene peroxide belongs to the class of organic compounds known as oxolanes. These are organic compounds containing an oxolane (tetrahydrofuran) ring, which is a saturated aliphatic five-member ring containing one oxygen and five carbon atoms. (3e,6s)-6-[(2r,5s)-5-[(2r,2's,5r,5'r)-5'-[(2s,4e)-6-hydroxy-6-methylhept-4-en-2-yl]-[2,2'-bioxolan]-5-yl]oxolan-2-yl]-2-methylhept-3-en-2-ol is found in Eurycoma longifolia. (3e,6s)-6-[(2r,5s)-5-[(2r,2's,5r,5'r)-5'-[(2s,4e)-6-hydroxy-6-methylhept-4-en-2-yl]-[2,2'-bioxolan]-5-yl]oxolan-2-yl]-2-methylhept-3-en-2-ol was first documented in 2018 (PMID: 29673138). Based on a literature review very few articles have been published on Longilene peroxide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032223392D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309032223392D          

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   -0.3700   -4.8068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3370   -4.2521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3919   -2.8001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
 10  2  1  1  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  1  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  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 21 31  1  0  0  0  0
 18 31  1  6  0  0  0
 17 32  1  0  0  0  0
 14 32  1  1  0  0  0
 13 33  1  0  0  0  0
 10 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0182843

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](C\C=C\C(C)(C)O)[C@H]1CC[C@H](O1)[C@H]1CC[C@@H](O1)[C@@H]1CC[C@@H](O1)[C@@H](C)C\C=C\C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C28H48O5/c1-19(9-7-17-27(3,4)29)21-11-13-23(31-21)25-15-16-26(33-25)24-14-12-22(32-24)20(2)10-8-18-28(5,6)30/h7-8,17-26,29-30H,9-16H2,1-6H3/b17-7+,18-8+/t19-,20-,21+,22+,23-,24-,25+,26+/m0/s1

> <INCHI_KEY>
JKCKDVJGGOMNHE-WBMRNAERSA-N

> <FORMULA>
C28H48O5

> <MOLECULAR_WEIGHT>
464.687

> <EXACT_MASS>
464.350174646

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
55.27944309144485

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3E,6S)-6-[(2R,5S)-5-[(2R,2'S,5R,5'R)-5'-[(2S,4E)-6-hydroxy-6-methylhept-4-en-2-yl]-[2,2'-bioxolane]-5-yl]oxolan-2-yl]-2-methylhept-3-en-2-ol

> <JCHEM_LOGP>
4.871529339666665

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.781315610600483

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.781315610600483

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2796244234004686

> <JCHEM_POLAR_SURFACE_AREA>
68.15

> <JCHEM_REFRACTIVITY>
134.7347

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3E,6S)-6-[(2R,5S)-5-[(2R,2'S,5R,5'R)-5'-[(2S,4E)-6-hydroxy-6-methylhept-4-en-2-yl]-[2,2'-bioxolane]-5-yl]oxolan-2-yl]-2-methylhept-3-en-2-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       4.377  -2.012   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.711  -2.782   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.045  -2.012   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.045  -0.472   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.378   0.298   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.378   1.838   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.378   3.378   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.838   1.838   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       9.918   1.838   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.711  -4.322   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.957  -5.227   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.481  -6.691   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.941  -6.691   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.036  -7.937   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.512  -9.402   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.266 -10.307   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.020  -9.402   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.555  -9.878   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.079 -11.342   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.461 -11.342   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.937  -9.878   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.401  -9.402   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.546 -10.432   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.721  -7.896   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.186  -7.420   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.506  -5.913   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.971  -5.437   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -8.436  -4.962   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -6.495  -3.973   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -7.447  -6.902   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -0.691  -8.973   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       2.496  -7.937   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       4.465  -5.227   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    2   11   33                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   33                                                  
CONECT   14   13   15   32                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   32                                                  
CONECT   18   17   19   31                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   31                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27                                                            
CONECT   31   21   18                                                       
CONECT   32   17   14                                                       
CONECT   33   13   10                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₈O₅

Average Mass

464.6870 Da

Monoisotopic Mass

464.35017 Da

IUPAC Name

(3E,6S)-6-[(2R,5S)-5-[(2R,2'S,5R,5'R)-5'-[(2S,4E)-6-hydroxy-6-methylhept-4-en-2-yl]-[2,2'-bioxolane]-5-yl]oxolan-2-yl]-2-methylhept-3-en-2-ol

Traditional Name

(3E,6S)-6-[(2R,5S)-5-[(2R,2'S,5R,5'R)-5'-[(2S,4E)-6-hydroxy-6-methylhept-4-en-2-yl]-[2,2'-bioxolane]-5-yl]oxolan-2-yl]-2-methylhept-3-en-2-ol

CAS Registry Number

Not Available

SMILES

C[C@@H](C\C=C\C(C)(C)O)[C@H]1CC[C@H](O1)[C@H]1CC[C@@H](O1)[C@@H]1CC[C@@H](O1)[C@@H](C)C\C=C\C(C)(C)O

InChI Identifier

InChI=1S/C28H48O5/c1-19(9-7-17-27(3,4)29)21-11-13-23(31-21)25-15-16-26(33-25)24-14-12-22(32-24)20(2)10-8-18-28(5,6)30/h7-8,17-26,29-30H,9-16H2,1-6H3/b17-7+,18-8+/t19-,20-,21+,22+,23-,24-,25+,26+/m0/s1

InChI Key

JKCKDVJGGOMNHE-WBMRNAERSA-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

Species Name	Source	Reference
Eurycoma longifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxolanes. These are organic compounds containing an oxolane (tetrahydrofuran) ring, which is a saturated aliphatic five-member ring containing one oxygen and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxolanes

Sub Class

Not Available

Direct Parent

Oxolanes

Alternative Parents

Substituents

Tertiary alcohol
Oxolane
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	4.87	ChemAxon
pKa (Strongest Acidic)	17.78	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	68.15 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	134.73 m³·mol⁻¹	ChemAxon
Polarizability	55.28 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00051309

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

101129808

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cen-Pacheco F, Perez Manriquez C, Luisa Souto M, Norte M, Fernandez JJ, Hernandez Daranas A: Marine Longilenes, Oxasqualenoids with Ser-Thr Protein Phosphatase 2A Inhibition Activity. Mar Drugs. 2018 Apr 17;16(4):131. doi: 10.3390/md16040131. [PubMed:29673138 ]
LOTUS database [Link]

Showing NP-Card for (3e,6s)-6-[(2r,5s)-5-[(2r,2's,5r,5'r)-5'-[(2s,4e)-6-hydroxy-6-methylhept-4-en-2-yl]-[2,2'-bioxolan]-5-yl]oxolan-2-yl]-2-methylhept-3-en-2-ol (NP0182843)

MOL for NP0182843 ((3e,6s)-6-[(2r,5s)-5-[(2r,2's,5r,5'r)-5'-[(2s,4e)-6-hydroxy-6-methylhept-4-en-2-yl]-[2,2'-bioxolan]-5-yl]oxolan-2-yl]-2-methylhept-3-en-2-ol)

3D MOL for NP0182843 ((3e,6s)-6-[(2r,5s)-5-[(2r,2's,5r,5'r)-5'-[(2s,4e)-6-hydroxy-6-methylhept-4-en-2-yl]-[2,2'-bioxolan]-5-yl]oxolan-2-yl]-2-methylhept-3-en-2-ol)

3D SDF for NP0182843 ((3e,6s)-6-[(2r,5s)-5-[(2r,2's,5r,5'r)-5'-[(2s,4e)-6-hydroxy-6-methylhept-4-en-2-yl]-[2,2'-bioxolan]-5-yl]oxolan-2-yl]-2-methylhept-3-en-2-ol)

3D-SDF for NP0182843 ((3e,6s)-6-[(2r,5s)-5-[(2r,2's,5r,5'r)-5'-[(2s,4e)-6-hydroxy-6-methylhept-4-en-2-yl]-[2,2'-bioxolan]-5-yl]oxolan-2-yl]-2-methylhept-3-en-2-ol)

PDB for NP0182843 ((3e,6s)-6-[(2r,5s)-5-[(2r,2's,5r,5'r)-5'-[(2s,4e)-6-hydroxy-6-methylhept-4-en-2-yl]-[2,2'-bioxolan]-5-yl]oxolan-2-yl]-2-methylhept-3-en-2-ol)

3D PDB for NP0182843 ((3e,6s)-6-[(2r,5s)-5-[(2r,2's,5r,5'r)-5'-[(2s,4e)-6-hydroxy-6-methylhept-4-en-2-yl]-[2,2'-bioxolan]-5-yl]oxolan-2-yl]-2-methylhept-3-en-2-ol)

SMILES for NP0182843 ((3e,6s)-6-[(2r,5s)-5-[(2r,2's,5r,5'r)-5'-[(2s,4e)-6-hydroxy-6-methylhept-4-en-2-yl]-[2,2'-bioxolan]-5-yl]oxolan-2-yl]-2-methylhept-3-en-2-ol)

INCHI for NP0182843 ((3e,6s)-6-[(2r,5s)-5-[(2r,2's,5r,5'r)-5'-[(2s,4e)-6-hydroxy-6-methylhept-4-en-2-yl]-[2,2'-bioxolan]-5-yl]oxolan-2-yl]-2-methylhept-3-en-2-ol)

Structure for NP0182843 ((3e,6s)-6-[(2r,5s)-5-[(2r,2's,5r,5'r)-5'-[(2s,4e)-6-hydroxy-6-methylhept-4-en-2-yl]-[2,2'-bioxolan]-5-yl]oxolan-2-yl]-2-methylhept-3-en-2-ol)

3D Structure for NP0182843 ((3e,6s)-6-[(2r,5s)-5-[(2r,2's,5r,5'r)-5'-[(2s,4e)-6-hydroxy-6-methylhept-4-en-2-yl]-[2,2'-bioxolan]-5-yl]oxolan-2-yl]-2-methylhept-3-en-2-ol)