NP-MRD: Showing NP-Card for (2e,5r,6e,10e)-11-[(2s,4s)-4-hydroxy-5,5-dimethyloxolan-2-yl]-1-(2-hydroxy-5-methoxy-3-methylphenyl)-3,7-dimethyldodeca-2,6,10-trien-5-yl acetate (NP0302056)

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Record Information

Version

2.0

Created at

2022-09-10 15:22:44 UTC

Updated at

2022-09-10 15:22:44 UTC

NP-MRD ID

NP0302056

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e,5r,6e,10e)-11-[(2s,4s)-4-hydroxy-5,5-dimethyloxolan-2-yl]-1-(2-hydroxy-5-methoxy-3-methylphenyl)-3,7-dimethyldodeca-2,6,10-trien-5-yl acetate

Description

(2E,5R,6E,10E)-11-[(2S,4S)-4-hydroxy-5,5-dimethyloxolan-2-yl]-1-(2-hydroxy-5-methoxy-3-methylphenyl)-3,7-dimethyldodeca-2,6,10-trien-5-yl acetate belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. Based on a literature review very few articles have been published on (2E,5R,6E,10E)-11-[(2S,4S)-4-hydroxy-5,5-dimethyloxolan-2-yl]-1-(2-hydroxy-5-methoxy-3-methylphenyl)-3,7-dimethyldodeca-2,6,10-trien-5-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102217222D          

 36 37  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652309102217222D          

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    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 24 22  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
 24 31  1  0  0  0  0
 15 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
  9 36  2  0  0  0  0
  3 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0302056

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(C)=C(O)C(C\C=C(/C)C[C@@H](OC(C)=O)\C=C(/C)CC\C=C(/C)[C@@H]2C[C@H](O)C(C)(C)O2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O6/c1-19(10-9-11-21(3)27-18-28(32)30(6,7)36-27)14-26(35-23(5)31)15-20(2)12-13-24-17-25(34-8)16-22(4)29(24)33/h11-12,14,16-17,26-28,32-33H,9-10,13,15,18H2,1-8H3/b19-14+,20-12+,21-11+/t26-,27-,28-/m0/s1

> <INCHI_KEY>
ZYDFZZLCOJUUHC-QQJDIDHASA-N

> <FORMULA>
C30H44O6

> <MOLECULAR_WEIGHT>
500.676

> <EXACT_MASS>
500.313789137

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
57.80509491536809

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,5R,6E,10E)-11-[(2S,4S)-4-hydroxy-5,5-dimethyloxolan-2-yl]-1-(2-hydroxy-5-methoxy-3-methylphenyl)-3,7-dimethyldodeca-2,6,10-trien-5-yl acetate

> <JCHEM_LOGP>
5.661114474333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.914747521510616

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.11020612299854

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2735192346143664

> <JCHEM_POLAR_SURFACE_AREA>
85.22

> <JCHEM_REFRACTIVITY>
146.17029999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2E,5R,6E,10E)-11-[(2S,4S)-4-hydroxy-5,5-dimethyloxolan-2-yl]-1-(2-hydroxy-5-methoxy-3-methylphenyl)-3,7-dimethyldodeca-2,6,10-trien-5-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  11.550   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  13.090   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002  13.860   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336  13.090   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002  15.400   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.756  16.305   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.232  17.770   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.327  19.016   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.772  17.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.611  19.301   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.278  18.090   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.248  16.305   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      10.669   6.160   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   36                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   32                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   31                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28   24                                                       
CONECT   32   15   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36    9    3                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

View in JSmol

Synonyms

Value	Source
(2E,5R,6E,10E)-11-[(2S,4S)-4-Hydroxy-5,5-dimethyloxolan-2-yl]-1-(2-hydroxy-5-methoxy-3-methylphenyl)-3,7-dimethyldodeca-2,6,10-trien-5-yl acetic acid	Generator

Chemical Formula

C₃₀H₄₄O₆

Average Mass

500.6760 Da

Monoisotopic Mass

500.31379 Da

IUPAC Name

(2E,5R,6E,10E)-11-[(2S,4S)-4-hydroxy-5,5-dimethyloxolan-2-yl]-1-(2-hydroxy-5-methoxy-3-methylphenyl)-3,7-dimethyldodeca-2,6,10-trien-5-yl acetate

Traditional Name

(2E,5R,6E,10E)-11-[(2S,4S)-4-hydroxy-5,5-dimethyloxolan-2-yl]-1-(2-hydroxy-5-methoxy-3-methylphenyl)-3,7-dimethyldodeca-2,6,10-trien-5-yl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC(C)=C(O)C(C\C=C(/C)C[C@@H](OC(C)=O)\C=C(/C)CC\C=C(/C)[C@@H]2C[C@H](O)C(C)(C)O2)=C1

InChI Identifier

InChI=1S/C30H44O6/c1-19(10-9-11-21(3)27-18-28(32)30(6,7)36-27)14-26(35-23(5)31)15-20(2)12-13-24-17-25(34-8)16-22(4)29(24)33/h11-12,14,16-17,26-28,32-33H,9-10,13,15,18H2,1-8H3/b19-14+,20-12+,21-11+/t26-,27-,28-/m0/s1

InChI Key

ZYDFZZLCOJUUHC-QQJDIDHASA-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 glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Diterpenoid
Fatty alcohol ester
Methoxyphenol
4-alkoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
O-cresol
Alkyl aryl ether
Toluene
Phenol
Monocyclic benzene moiety
Benzenoid
Tetrahydrofuran
Carboxylic acid ester
Secondary alcohol
Ether
Organoheterocyclic compound
Oxacycle
Dialkyl ether
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen 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
logP	5.66	ChemAxon
pKa (Strongest Acidic)	10.11	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	146.17 m³·mol⁻¹	ChemAxon
Polarizability	57.81 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

163193890

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e,5r,6e,10e)-11-[(2s,4s)-4-hydroxy-5,5-dimethyloxolan-2-yl]-1-(2-hydroxy-5-methoxy-3-methylphenyl)-3,7-dimethyldodeca-2,6,10-trien-5-yl acetate (NP0302056)

MOL for NP0302056 ((2e,5r,6e,10e)-11-[(2s,4s)-4-hydroxy-5,5-dimethyloxolan-2-yl]-1-(2-hydroxy-5-methoxy-3-methylphenyl)-3,7-dimethyldodeca-2,6,10-trien-5-yl acetate)

3D MOL for NP0302056 ((2e,5r,6e,10e)-11-[(2s,4s)-4-hydroxy-5,5-dimethyloxolan-2-yl]-1-(2-hydroxy-5-methoxy-3-methylphenyl)-3,7-dimethyldodeca-2,6,10-trien-5-yl acetate)

3D SDF for NP0302056 ((2e,5r,6e,10e)-11-[(2s,4s)-4-hydroxy-5,5-dimethyloxolan-2-yl]-1-(2-hydroxy-5-methoxy-3-methylphenyl)-3,7-dimethyldodeca-2,6,10-trien-5-yl acetate)

3D-SDF for NP0302056 ((2e,5r,6e,10e)-11-[(2s,4s)-4-hydroxy-5,5-dimethyloxolan-2-yl]-1-(2-hydroxy-5-methoxy-3-methylphenyl)-3,7-dimethyldodeca-2,6,10-trien-5-yl acetate)

PDB for NP0302056 ((2e,5r,6e,10e)-11-[(2s,4s)-4-hydroxy-5,5-dimethyloxolan-2-yl]-1-(2-hydroxy-5-methoxy-3-methylphenyl)-3,7-dimethyldodeca-2,6,10-trien-5-yl acetate)

3D PDB for NP0302056 ((2e,5r,6e,10e)-11-[(2s,4s)-4-hydroxy-5,5-dimethyloxolan-2-yl]-1-(2-hydroxy-5-methoxy-3-methylphenyl)-3,7-dimethyldodeca-2,6,10-trien-5-yl acetate)

SMILES for NP0302056 ((2e,5r,6e,10e)-11-[(2s,4s)-4-hydroxy-5,5-dimethyloxolan-2-yl]-1-(2-hydroxy-5-methoxy-3-methylphenyl)-3,7-dimethyldodeca-2,6,10-trien-5-yl acetate)

INCHI for NP0302056 ((2e,5r,6e,10e)-11-[(2s,4s)-4-hydroxy-5,5-dimethyloxolan-2-yl]-1-(2-hydroxy-5-methoxy-3-methylphenyl)-3,7-dimethyldodeca-2,6,10-trien-5-yl acetate)

Structure for NP0302056 ((2e,5r,6e,10e)-11-[(2s,4s)-4-hydroxy-5,5-dimethyloxolan-2-yl]-1-(2-hydroxy-5-methoxy-3-methylphenyl)-3,7-dimethyldodeca-2,6,10-trien-5-yl acetate)

3D Structure for NP0302056 ((2e,5r,6e,10e)-11-[(2s,4s)-4-hydroxy-5,5-dimethyloxolan-2-yl]-1-(2-hydroxy-5-methoxy-3-methylphenyl)-3,7-dimethyldodeca-2,6,10-trien-5-yl acetate)