NP-MRD: Showing NP-Card for (2s,3r,4s,5r)-2-{4-hydroxy-5-[(2e,6e,10e)-14-hydroxy-3,7,11-trimethyltetradeca-2,6,10-trien-1-yl]-2,3-dimethylphenoxy}oxane-3,4,5-triol (NP0319630)

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Record Information

Version

2.0

Created at

2022-09-11 20:45:50 UTC

Updated at

2022-09-11 20:45:50 UTC

NP-MRD ID

NP0319630

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5r)-2-{4-hydroxy-5-[(2e,6e,10e)-14-hydroxy-3,7,11-trimethyltetradeca-2,6,10-trien-1-yl]-2,3-dimethylphenoxy}oxane-3,4,5-triol

Description

Lurlenol, also known as lurlene C, belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. (2s,3r,4s,5r)-2-{4-hydroxy-5-[(2e,6e,10e)-14-hydroxy-3,7,11-trimethyltetradeca-2,6,10-trien-1-yl]-2,3-dimethylphenoxy}oxane-3,4,5-triol is found in Chlamydomonas allensworthii. Based on a literature review very few articles have been published on Lurlenol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112222452D          

 37 38  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309112222452D          

 37 38  0  0  1  0            999 V2000
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    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    7.0125    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  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  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  1  0  0  0
 12 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 10 27  1  0  0  0  0
 27 28  1  0  0  0  0
  2 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0319630

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(CCCO)=C/CC\C(C)=C\CC\C(C)=C\CC1=CC(O[C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)=C(C)C(C)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O7/c1-19(9-6-11-20(2)13-8-16-31)10-7-12-21(3)14-15-24-17-26(22(4)23(5)27(24)33)37-30-29(35)28(34)25(32)18-36-30/h10-11,14,17,25,28-35H,6-9,12-13,15-16,18H2,1-5H3/b19-10+,20-11+,21-14+/t25-,28+,29-,30+/m1/s1

> <INCHI_KEY>
HGCVITHBCNPTOB-BIIYHIOKSA-N

> <FORMULA>
C30H46O7

> <MOLECULAR_WEIGHT>
518.691

> <EXACT_MASS>
518.324353821

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
61.35578173303745

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5R)-2-{4-hydroxy-5-[(2E,6E,10E)-14-hydroxy-3,7,11-trimethyltetradeca-2,6,10-trien-1-yl]-2,3-dimethylphenoxy}oxane-3,4,5-triol

> <JCHEM_LOGP>
5.2556790626666645

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.238044260624907

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.109023792895352

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9713055604709981

> <JCHEM_POLAR_SURFACE_AREA>
119.61000000000001

> <JCHEM_REFRACTIVITY>
149.2628

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R)-2-{4-hydroxy-5-[(2E,6E,10E)-14-hydroxy-3,7,11-trimethyltetradeca-2,6,10-trien-1-yl]-2,3-dimethylphenoxy}oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   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       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.669   9.240   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.669  10.780   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.336  11.550   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.003  11.550   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.337  10.780   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      14.670  11.550   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      14.670  13.090   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   29                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   27                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   23                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   14   22                                                  
CONECT   22   21                                                            
CONECT   23   12   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   10   28                                                  
CONECT   28   27                                                            
CONECT   29    2   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   76    0
END

View in JSmol

Synonyms

Value	Source
Lurlene C	MeSH

Chemical Formula

C₃₀H₄₆O₇

Average Mass

518.6910 Da

Monoisotopic Mass

518.32435 Da

IUPAC Name

(2S,3R,4S,5R)-2-{4-hydroxy-5-[(2E,6E,10E)-14-hydroxy-3,7,11-trimethyltetradeca-2,6,10-trien-1-yl]-2,3-dimethylphenoxy}oxane-3,4,5-triol

Traditional Name

(2S,3R,4S,5R)-2-{4-hydroxy-5-[(2E,6E,10E)-14-hydroxy-3,7,11-trimethyltetradeca-2,6,10-trien-1-yl]-2,3-dimethylphenoxy}oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

C\C(CCCO)=C/CC\C(C)=C\CC\C(C)=C\CC1=CC(O[C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)=C(C)C(C)=C1O

InChI Identifier

InChI=1S/C30H46O7/c1-19(9-6-11-20(2)13-8-16-31)10-7-12-21(3)14-15-24-17-26(22(4)23(5)27(24)33)37-30-29(35)28(34)25(32)18-36-30/h10-11,14,17,25,28-35H,6-9,12-13,15-16,18H2,1-5H3/b19-10+,20-11+,21-14+/t25-,28+,29-,30+/m1/s1

InChI Key

HGCVITHBCNPTOB-BIIYHIOKSA-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
Chlamydomonas allensworthii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Farsesane sesquiterpenoid
Sesquiterpenoid
Long chain fatty alcohol
O-glycosyl compound
Pentose monosaccharide
4-alkoxyphenol
Fatty alcohol
Phenoxy compound
O-xylene
Xylene
M-cresol
O-cresol
Phenol ether
Phenol
Monocyclic benzene moiety
Fatty acyl
Monosaccharide
Benzenoid
Oxane
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Alcohol
Hydrocarbon derivative
Primary 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	5.26	ChemAxon
pKa (Strongest Acidic)	10.11	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	119.61 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	149.26 m³·mol⁻¹	ChemAxon
Polarizability	61.36 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

9257036

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11081889

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5r)-2-{4-hydroxy-5-[(2e,6e,10e)-14-hydroxy-3,7,11-trimethyltetradeca-2,6,10-trien-1-yl]-2,3-dimethylphenoxy}oxane-3,4,5-triol (NP0319630)

MOL for NP0319630 ((2s,3r,4s,5r)-2-{4-hydroxy-5-[(2e,6e,10e)-14-hydroxy-3,7,11-trimethyltetradeca-2,6,10-trien-1-yl]-2,3-dimethylphenoxy}oxane-3,4,5-triol)

3D MOL for NP0319630 ((2s,3r,4s,5r)-2-{4-hydroxy-5-[(2e,6e,10e)-14-hydroxy-3,7,11-trimethyltetradeca-2,6,10-trien-1-yl]-2,3-dimethylphenoxy}oxane-3,4,5-triol)

3D SDF for NP0319630 ((2s,3r,4s,5r)-2-{4-hydroxy-5-[(2e,6e,10e)-14-hydroxy-3,7,11-trimethyltetradeca-2,6,10-trien-1-yl]-2,3-dimethylphenoxy}oxane-3,4,5-triol)

3D-SDF for NP0319630 ((2s,3r,4s,5r)-2-{4-hydroxy-5-[(2e,6e,10e)-14-hydroxy-3,7,11-trimethyltetradeca-2,6,10-trien-1-yl]-2,3-dimethylphenoxy}oxane-3,4,5-triol)

PDB for NP0319630 ((2s,3r,4s,5r)-2-{4-hydroxy-5-[(2e,6e,10e)-14-hydroxy-3,7,11-trimethyltetradeca-2,6,10-trien-1-yl]-2,3-dimethylphenoxy}oxane-3,4,5-triol)

3D PDB for NP0319630 ((2s,3r,4s,5r)-2-{4-hydroxy-5-[(2e,6e,10e)-14-hydroxy-3,7,11-trimethyltetradeca-2,6,10-trien-1-yl]-2,3-dimethylphenoxy}oxane-3,4,5-triol)

SMILES for NP0319630 ((2s,3r,4s,5r)-2-{4-hydroxy-5-[(2e,6e,10e)-14-hydroxy-3,7,11-trimethyltetradeca-2,6,10-trien-1-yl]-2,3-dimethylphenoxy}oxane-3,4,5-triol)

INCHI for NP0319630 ((2s,3r,4s,5r)-2-{4-hydroxy-5-[(2e,6e,10e)-14-hydroxy-3,7,11-trimethyltetradeca-2,6,10-trien-1-yl]-2,3-dimethylphenoxy}oxane-3,4,5-triol)

Structure for NP0319630 ((2s,3r,4s,5r)-2-{4-hydroxy-5-[(2e,6e,10e)-14-hydroxy-3,7,11-trimethyltetradeca-2,6,10-trien-1-yl]-2,3-dimethylphenoxy}oxane-3,4,5-triol)

3D Structure for NP0319630 ((2s,3r,4s,5r)-2-{4-hydroxy-5-[(2e,6e,10e)-14-hydroxy-3,7,11-trimethyltetradeca-2,6,10-trien-1-yl]-2,3-dimethylphenoxy}oxane-3,4,5-triol)