NP-MRD: Showing NP-Card for (2r,5r)-5-[(4e,8e)-10-(5-hydroxy-2-methoxy-3-methylphenyl)-4,8-dimethyl-6-oxodeca-4,8-dien-1-yl]-2-(2-hydroxypropan-2-yl)-5-methyloxolan-3-one (NP0153026)

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Record Information

Version

2.0

Created at

2022-09-02 09:36:50 UTC

Updated at

2022-09-02 09:36:51 UTC

NP-MRD ID

NP0153026

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,5r)-5-[(4e,8e)-10-(5-hydroxy-2-methoxy-3-methylphenyl)-4,8-dimethyl-6-oxodeca-4,8-dien-1-yl]-2-(2-hydroxypropan-2-yl)-5-methyloxolan-3-one

Description

(2R,5R)-5-[(4E,8E)-10-(5-hydroxy-2-methoxy-3-methylphenyl)-4,8-dimethyl-6-oxodeca-4,8-dien-1-yl]-2-(2-hydroxypropan-2-yl)-5-methyloxolan-3-one belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (2r,5r)-5-[(4e,8e)-10-(5-hydroxy-2-methoxy-3-methylphenyl)-4,8-dimethyl-6-oxodeca-4,8-dien-1-yl]-2-(2-hydroxypropan-2-yl)-5-methyloxolan-3-one is found in Cystoseira usneoides. Based on a literature review very few articles have been published on (2R,5R)-5-[(4E,8E)-10-(5-hydroxy-2-methoxy-3-methylphenyl)-4,8-dimethyl-6-oxodeca-4,8-dien-1-yl]-2-(2-hydroxypropan-2-yl)-5-methyloxolan-3-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022211362D          

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 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 29 34  1  0  0  0  0
 24 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0153026

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C)C=C(O)C=C1C\C=C(/C)CC(=O)\C=C(/C)CCC[C@]1(C)CC(=O)[C@H](O1)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C28H40O6/c1-18(9-8-12-28(6)17-24(31)26(34-28)27(4,5)32)13-22(29)14-19(2)10-11-21-16-23(30)15-20(3)25(21)33-7/h10,13,15-16,26,30,32H,8-9,11-12,14,17H2,1-7H3/b18-13+,19-10+/t26-,28+/m0/s1

> <INCHI_KEY>
NOLBKOFZJOKNIL-JQBVMMCNSA-N

> <FORMULA>
C28H40O6

> <MOLECULAR_WEIGHT>
472.622

> <EXACT_MASS>
472.282489008

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
52.903318377001014

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,5R)-5-[(4E,8E)-10-(5-hydroxy-2-methoxy-3-methylphenyl)-4,8-dimethyl-6-oxodeca-4,8-dien-1-yl]-2-(2-hydroxypropan-2-yl)-5-methyloxolan-3-one

> <ALOGPS_LOGP>
4.86

> <JCHEM_LOGP>
5.439693492333332

> <ALOGPS_LOGS>
-5.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.140549233820678

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.99647207656995

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1734227324440454

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
135.8687

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.90e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,5R)-5-[(4E,8E)-10-(5-hydroxy-2-methoxy-3-methylphenyl)-4,8-dimethyl-6-oxodeca-4,8-dien-1-yl]-2-(2-hydroxypropan-2-yl)-5-methyloxolan-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      19.964  18.252   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      20.440  16.787   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      21.947  16.467   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.977  17.611   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.501  19.076   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      24.483  17.291   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.959  15.826   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      26.466  15.506   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      23.929  14.682   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.423  15.002   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.392  13.858   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.868  12.393   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.838  11.249   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.331  11.569   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.313   9.784   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.283   8.640   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      18.777   8.960   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      20.759   7.175   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      19.728   6.031   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      18.222   6.351   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      20.204   4.566   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.174   3.421   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      19.650   1.957   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.619   0.812   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.589   1.957   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      19.865  -0.093   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      19.389  -1.557   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      20.294  -2.803   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      17.849  -1.557   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.944  -2.803   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.039  -4.049   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      15.698  -1.898   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      18.190  -3.709   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      17.373  -0.093   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    3   11                                                  
CONECT   11   10   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   34                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   34                                                  
CONECT   30   29   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30                                                            
CONECT   34   29   24                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₀O₆

Average Mass

472.6220 Da

Monoisotopic Mass

472.28249 Da

IUPAC Name

(2R,5R)-5-[(4E,8E)-10-(5-hydroxy-2-methoxy-3-methylphenyl)-4,8-dimethyl-6-oxodeca-4,8-dien-1-yl]-2-(2-hydroxypropan-2-yl)-5-methyloxolan-3-one

Traditional Name

(2R,5R)-5-[(4E,8E)-10-(5-hydroxy-2-methoxy-3-methylphenyl)-4,8-dimethyl-6-oxodeca-4,8-dien-1-yl]-2-(2-hydroxypropan-2-yl)-5-methyloxolan-3-one

CAS Registry Number

Not Available

SMILES

COC1=C(C)C=C(O)C=C1C\C=C(/C)CC(=O)\C=C(/C)CCC[C@]1(C)CC(=O)[C@H](O1)C(C)(C)O

InChI Identifier

InChI=1S/C28H40O6/c1-18(9-8-12-28(6)17-24(31)26(34-28)27(4,5)32)13-22(29)14-19(2)10-11-21-16-23(30)15-20(3)25(21)33-7/h10,13,15-16,26,30,32H,8-9,11-12,14,17H2,1-7H3/b18-13+,19-10+/t26-,28+/m0/s1

InChI Key

NOLBKOFZJOKNIL-JQBVMMCNSA-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
Cystoseira usneoides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Methoxyphenol
4-alkoxyphenol
Phenoxy compound
Methoxybenzene
Phenol ether
M-cresol
Anisole
1-hydroxy-2-unsubstituted benzenoid
Toluene
Phenol
Alkyl aryl ether
Benzenoid
3-furanone
Monocyclic benzene moiety
Alpha,beta-unsaturated ketone
Tetrahydrofuran
Tertiary alcohol
Enone
Acryloyl-group
Cyclic ketone
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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
logP	4.86	ALOGPS
logP	5.44	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	10	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	135.87 m³·mol⁻¹	ChemAxon
Polarizability	52.9 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

162817092

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,5r)-5-[(4e,8e)-10-(5-hydroxy-2-methoxy-3-methylphenyl)-4,8-dimethyl-6-oxodeca-4,8-dien-1-yl]-2-(2-hydroxypropan-2-yl)-5-methyloxolan-3-one (NP0153026)

MOL for NP0153026 ((2r,5r)-5-[(4e,8e)-10-(5-hydroxy-2-methoxy-3-methylphenyl)-4,8-dimethyl-6-oxodeca-4,8-dien-1-yl]-2-(2-hydroxypropan-2-yl)-5-methyloxolan-3-one)

3D MOL for NP0153026 ((2r,5r)-5-[(4e,8e)-10-(5-hydroxy-2-methoxy-3-methylphenyl)-4,8-dimethyl-6-oxodeca-4,8-dien-1-yl]-2-(2-hydroxypropan-2-yl)-5-methyloxolan-3-one)

3D SDF for NP0153026 ((2r,5r)-5-[(4e,8e)-10-(5-hydroxy-2-methoxy-3-methylphenyl)-4,8-dimethyl-6-oxodeca-4,8-dien-1-yl]-2-(2-hydroxypropan-2-yl)-5-methyloxolan-3-one)

3D-SDF for NP0153026 ((2r,5r)-5-[(4e,8e)-10-(5-hydroxy-2-methoxy-3-methylphenyl)-4,8-dimethyl-6-oxodeca-4,8-dien-1-yl]-2-(2-hydroxypropan-2-yl)-5-methyloxolan-3-one)

PDB for NP0153026 ((2r,5r)-5-[(4e,8e)-10-(5-hydroxy-2-methoxy-3-methylphenyl)-4,8-dimethyl-6-oxodeca-4,8-dien-1-yl]-2-(2-hydroxypropan-2-yl)-5-methyloxolan-3-one)

3D PDB for NP0153026 ((2r,5r)-5-[(4e,8e)-10-(5-hydroxy-2-methoxy-3-methylphenyl)-4,8-dimethyl-6-oxodeca-4,8-dien-1-yl]-2-(2-hydroxypropan-2-yl)-5-methyloxolan-3-one)

SMILES for NP0153026 ((2r,5r)-5-[(4e,8e)-10-(5-hydroxy-2-methoxy-3-methylphenyl)-4,8-dimethyl-6-oxodeca-4,8-dien-1-yl]-2-(2-hydroxypropan-2-yl)-5-methyloxolan-3-one)

INCHI for NP0153026 ((2r,5r)-5-[(4e,8e)-10-(5-hydroxy-2-methoxy-3-methylphenyl)-4,8-dimethyl-6-oxodeca-4,8-dien-1-yl]-2-(2-hydroxypropan-2-yl)-5-methyloxolan-3-one)

Structure for NP0153026 ((2r,5r)-5-[(4e,8e)-10-(5-hydroxy-2-methoxy-3-methylphenyl)-4,8-dimethyl-6-oxodeca-4,8-dien-1-yl]-2-(2-hydroxypropan-2-yl)-5-methyloxolan-3-one)

3D Structure for NP0153026 ((2r,5r)-5-[(4e,8e)-10-(5-hydroxy-2-methoxy-3-methylphenyl)-4,8-dimethyl-6-oxodeca-4,8-dien-1-yl]-2-(2-hydroxypropan-2-yl)-5-methyloxolan-3-one)