NP-MRD: Showing NP-Card for (4e,8e,12e)-14-{2-hydroxy-3,4-dimethyl-5-[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]phenyl}-4,8,12-trimethyltetradeca-4,8,12-trienoic acid (NP0244786)

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Record Information

Version

2.0

Created at

2022-09-07 05:39:36 UTC

Updated at

2022-09-07 05:39:36 UTC

NP-MRD ID

NP0244786

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4e,8e,12e)-14-{2-hydroxy-3,4-dimethyl-5-[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]phenyl}-4,8,12-trimethyltetradeca-4,8,12-trienoic acid

Description

Lurlene 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. (4e,8e,12e)-14-{2-hydroxy-3,4-dimethyl-5-[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]phenyl}-4,8,12-trimethyltetradeca-4,8,12-trienoic acid is found in Chlamydomonas allensworthii. (4e,8e,12e)-14-{2-hydroxy-3,4-dimethyl-5-[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]phenyl}-4,8,12-trimethyltetradeca-4,8,12-trienoic acid was first documented in 1996 (PMID: 8917459). Based on a literature review very few articles have been published on Lurlene.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072207392D          

 37 38  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072207392D          

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   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    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
   -5.7158    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    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
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  1  0  0  0
 12 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 10 26  1  0  0  0  0
 26 27  1  0  0  0  0
  2 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0244786

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O7/c1-18(9-7-11-20(3)13-15-26(32)33)8-6-10-19(2)12-14-23-16-24(21(4)22(5)27(23)34)30-29(36)28(35)25(31)17-37-30/h8,11-12,16,25,28-31,34-36H,6-7,9-10,13-15,17H2,1-5H3,(H,32,33)/b18-8+,19-12+,20-11+/t25-,28+,29-,30+/m1/s1

> <INCHI_KEY>
RLPQQDHLHYSRQE-JXXPZVEBSA-N

> <FORMULA>
C30H44O7

> <MOLECULAR_WEIGHT>
516.675

> <EXACT_MASS>
516.308703757

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
60.01557493512636

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4E,8E,12E)-14-{2-hydroxy-3,4-dimethyl-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]phenyl}-4,8,12-trimethyltetradeca-4,8,12-trienoic acid

> <JCHEM_LOGP>
5.186428424333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.746829099175468

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.928864274407132

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5229002821135458

> <JCHEM_POLAR_SURFACE_AREA>
127.45

> <JCHEM_REFRACTIVITY>
147.99250000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4E,8E,12E)-14-{2-hydroxy-3,4-dimethyl-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]phenyl}-4,8,12-trimethyltetradeca-4,8,12-trienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   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  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -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  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.335  10.780   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.001  11.550   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -6.668  11.550   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -8.002  10.780   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -9.336  11.550   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0     -10.669  10.780   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -9.336  13.090   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   28                                                  
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   26                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   22                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   13   21                                                  
CONECT   21   20                                                            
CONECT   22   12   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   10   27                                                  
CONECT   27   26                                                            
CONECT   28    2   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₄O₇

Average Mass

516.6750 Da

Monoisotopic Mass

516.30870 Da

IUPAC Name

(4E,8E,12E)-14-{2-hydroxy-3,4-dimethyl-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]phenyl}-4,8,12-trimethyltetradeca-4,8,12-trienoic acid

Traditional Name

(4E,8E,12E)-14-{2-hydroxy-3,4-dimethyl-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]phenyl}-4,8,12-trimethyltetradeca-4,8,12-trienoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C30H44O7/c1-18(9-7-11-20(3)13-15-26(32)33)8-6-10-19(2)12-14-23-16-24(21(4)22(5)27(23)34)30-29(36)28(35)25(31)17-37-30/h8,11-12,16,25,28-31,34-36H,6-7,9-10,13-15,17H2,1-5H3,(H,32,33)/b18-8+,19-12+,20-11+/t25-,28+,29-,30+/m1/s1

InChI Key

RLPQQDHLHYSRQE-JXXPZVEBSA-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
Sesquiterpenoid
Farsesane sesquiterpenoid
Long-chain fatty acid
M-cresol
O-xylene
Xylene
O-cresol
Branched fatty acid
Heterocyclic fatty acid
Phenol
Hydroxy fatty acid
Methyl-branched fatty acid
Monocyclic benzene moiety
Unsaturated fatty acid
Benzenoid
Fatty acid
Oxane
Fatty acyl
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Oxacycle
Monocarboxylic acid or derivatives
Polyol
Organoheterocyclic compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxide
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	5.19	ChemAxon
pKa (Strongest Acidic)	4.93	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.45 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	147.99 m³·mol⁻¹	ChemAxon
Polarizability	60.02 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

Lurlene McDaniel

METLIN ID

Not Available

PubChem Compound

101693588

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jaenicke L, Starr RC: The lurlenes, a new class of plastoquinone-related mating pheromones from Chlamydomonas allensworthii (Chlorophyceae). Eur J Biochem. 1996 Oct 15;241(2):581-5. doi: 10.1111/j.1432-1033.1996.00581.x. [PubMed:8917459 ]
LOTUS database [Link]

Showing NP-Card for (4e,8e,12e)-14-{2-hydroxy-3,4-dimethyl-5-[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]phenyl}-4,8,12-trimethyltetradeca-4,8,12-trienoic acid (NP0244786)

MOL for NP0244786 ((4e,8e,12e)-14-{2-hydroxy-3,4-dimethyl-5-[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]phenyl}-4,8,12-trimethyltetradeca-4,8,12-trienoic acid)

3D MOL for NP0244786 ((4e,8e,12e)-14-{2-hydroxy-3,4-dimethyl-5-[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]phenyl}-4,8,12-trimethyltetradeca-4,8,12-trienoic acid)

3D SDF for NP0244786 ((4e,8e,12e)-14-{2-hydroxy-3,4-dimethyl-5-[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]phenyl}-4,8,12-trimethyltetradeca-4,8,12-trienoic acid)

3D-SDF for NP0244786 ((4e,8e,12e)-14-{2-hydroxy-3,4-dimethyl-5-[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]phenyl}-4,8,12-trimethyltetradeca-4,8,12-trienoic acid)

PDB for NP0244786 ((4e,8e,12e)-14-{2-hydroxy-3,4-dimethyl-5-[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]phenyl}-4,8,12-trimethyltetradeca-4,8,12-trienoic acid)

3D PDB for NP0244786 ((4e,8e,12e)-14-{2-hydroxy-3,4-dimethyl-5-[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]phenyl}-4,8,12-trimethyltetradeca-4,8,12-trienoic acid)

SMILES for NP0244786 ((4e,8e,12e)-14-{2-hydroxy-3,4-dimethyl-5-[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]phenyl}-4,8,12-trimethyltetradeca-4,8,12-trienoic acid)

INCHI for NP0244786 ((4e,8e,12e)-14-{2-hydroxy-3,4-dimethyl-5-[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]phenyl}-4,8,12-trimethyltetradeca-4,8,12-trienoic acid)

Structure for NP0244786 ((4e,8e,12e)-14-{2-hydroxy-3,4-dimethyl-5-[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]phenyl}-4,8,12-trimethyltetradeca-4,8,12-trienoic acid)

3D Structure for NP0244786 ((4e,8e,12e)-14-{2-hydroxy-3,4-dimethyl-5-[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]phenyl}-4,8,12-trimethyltetradeca-4,8,12-trienoic acid)